CN109705175B - 使用模拟移动床色谱纯化中性人乳寡糖的方法 - Google Patents
使用模拟移动床色谱纯化中性人乳寡糖的方法 Download PDFInfo
- Publication number
- CN109705175B CN109705175B CN201811603666.0A CN201811603666A CN109705175B CN 109705175 B CN109705175 B CN 109705175B CN 201811603666 A CN201811603666 A CN 201811603666A CN 109705175 B CN109705175 B CN 109705175B
- Authority
- CN
- China
- Prior art keywords
- solution
- human milk
- lacto
- neutral
- chromatography
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 230000007935 neutral effect Effects 0.000 title claims abstract description 117
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 77
- 150000002482 oligosaccharides Chemical class 0.000 title claims abstract description 77
- 238000000034 method Methods 0.000 title claims abstract description 70
- 235000020256 human milk Nutrition 0.000 title claims abstract description 64
- 210000004251 human milk Anatomy 0.000 title claims abstract description 64
- 238000004587 chromatography analysis Methods 0.000 title claims description 68
- 238000000746 purification Methods 0.000 claims abstract description 46
- 238000001694 spray drying Methods 0.000 claims abstract description 9
- 239000000243 solution Substances 0.000 claims description 126
- 229940062827 2'-fucosyllactose Drugs 0.000 claims description 71
- HWHQUWQCBPAQQH-UHFFFAOYSA-N 2-O-alpha-L-Fucosyl-lactose Natural products OC1C(O)C(O)C(C)OC1OC1C(O)C(O)C(CO)OC1OC(C(O)CO)C(O)C(O)C=O HWHQUWQCBPAQQH-UHFFFAOYSA-N 0.000 claims description 71
- HWHQUWQCBPAQQH-BWRPKUOHSA-N 2-fucosyllactose Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O HWHQUWQCBPAQQH-BWRPKUOHSA-N 0.000 claims description 71
- SNFSYLYCDAVZGP-UHFFFAOYSA-N UNPD26986 Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(OC(O)C(O)C2O)CO)OC(CO)C(O)C1O SNFSYLYCDAVZGP-UHFFFAOYSA-N 0.000 claims description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 48
- 239000000356 contaminant Substances 0.000 claims description 33
- 238000001728 nano-filtration Methods 0.000 claims description 33
- 239000003480 eluent Substances 0.000 claims description 30
- 239000000284 extract Substances 0.000 claims description 29
- 239000012045 crude solution Substances 0.000 claims description 25
- 238000000855 fermentation Methods 0.000 claims description 23
- 230000004151 fermentation Effects 0.000 claims description 23
- 238000001914 filtration Methods 0.000 claims description 19
- 239000012607 strong cation exchange resin Substances 0.000 claims description 19
- 230000000813 microbial effect Effects 0.000 claims description 18
- AXQLFFDZXPOFPO-UHFFFAOYSA-N UNPD216 Natural products O1C(CO)C(O)C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(=O)C)C1OC(C1O)C(O)C(CO)OC1OC1C(O)C(O)C(O)OC1CO AXQLFFDZXPOFPO-UHFFFAOYSA-N 0.000 claims description 16
- AXQLFFDZXPOFPO-UNTPKZLMSA-N beta-D-Galp-(1->3)-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-beta-D-Glcp Chemical compound O([C@@H]1O[C@H](CO)[C@H](O)[C@@H]([C@H]1O)O[C@H]1[C@@H]([C@H]([C@H](O)[C@@H](CO)O1)O[C@H]1[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O1)O)NC(=O)C)[C@H]1[C@H](O)[C@@H](O)[C@H](O)O[C@@H]1CO AXQLFFDZXPOFPO-UNTPKZLMSA-N 0.000 claims description 16
- 238000000909 electrodialysis Methods 0.000 claims description 16
- USIPEGYTBGEPJN-UHFFFAOYSA-N lacto-N-tetraose Natural products O1C(CO)C(O)C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(=O)C)C1OC1C(O)C(CO)OC(OC(C(O)CO)C(O)C(O)C=O)C1O USIPEGYTBGEPJN-UHFFFAOYSA-N 0.000 claims description 16
- 239000007921 spray Substances 0.000 claims description 16
- 238000005277 cation exchange chromatography Methods 0.000 claims description 9
- 238000011210 chromatographic step Methods 0.000 claims description 9
- IEQCXFNWPAHHQR-UHFFFAOYSA-N lacto-N-neotetraose Natural products OCC1OC(OC2C(C(OC3C(OC(O)C(O)C3O)CO)OC(CO)C2O)O)C(NC(=O)C)C(O)C1OC1OC(CO)C(O)C(O)C1O IEQCXFNWPAHHQR-UHFFFAOYSA-N 0.000 claims description 9
- 229940062780 lacto-n-neotetraose Drugs 0.000 claims description 9
- RBMYDHMFFAVMMM-PLQWBNBWSA-N neolactotetraose Chemical compound O([C@H]1[C@H](O)[C@H]([C@@H](O[C@@H]1CO)O[C@@H]1[C@H]([C@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)O[C@H](CO)[C@@H]1O)O)NC(=O)C)[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O RBMYDHMFFAVMMM-PLQWBNBWSA-N 0.000 claims description 9
- AUNPEJDACLEKSC-ZAYDSPBTSA-N 3-fucosyllactose Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@H](OC(O)[C@H](O)[C@H]2O)CO)O[C@H](CO)[C@@H]1O AUNPEJDACLEKSC-ZAYDSPBTSA-N 0.000 claims description 7
- 238000005571 anion exchange chromatography Methods 0.000 claims description 7
- 238000000502 dialysis Methods 0.000 claims description 7
- 150000004044 tetrasaccharides Chemical class 0.000 claims description 7
- 150000004043 trisaccharides Chemical class 0.000 claims description 7
- 238000013375 chromatographic separation Methods 0.000 claims description 6
- 239000012608 weak cation exchange resin Substances 0.000 claims description 6
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims description 5
- ODDPRQJTYDIWJU-UHFFFAOYSA-N 3'-beta-D-galactopyranosyl-lactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(OC(O)C(O)C2O)CO)OC(CO)C1O ODDPRQJTYDIWJU-UHFFFAOYSA-N 0.000 claims description 5
- WJPIUUDKRHCAEL-UHFFFAOYSA-N 3FL Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(O)C(O)C(CO)O2)O)C(CO)OC(O)C1O WJPIUUDKRHCAEL-UHFFFAOYSA-N 0.000 claims description 5
- TVVLIFCVJJSLBL-SEHWTJTBSA-N Lacto-N-fucopentaose V Chemical compound O[C@H]1C(O)C(O)[C@H](C)O[C@H]1OC([C@@H](O)C=O)[C@@H](C(O)CO)O[C@H]1[C@H](O)[C@@H](OC2[C@@H](C(OC3[C@@H](C(O)C(O)[C@@H](CO)O3)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](O)[C@@H](CO)O1 TVVLIFCVJJSLBL-SEHWTJTBSA-N 0.000 claims description 5
- RJTOFDPWCJDYFZ-SPVZFZGWSA-N Lacto-N-triaose Chemical compound CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)O[C@H](CO)[C@@H]1O RJTOFDPWCJDYFZ-SPVZFZGWSA-N 0.000 claims description 5
- FZIVHOUANIQOMU-YIHIYSSUSA-N alpha-L-Fucp-(1->2)-beta-D-Galp-(1->3)-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-D-Glcp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@@H]2[C@H]([C@H](O[C@@H]3[C@H]([C@H](O[C@@H]4[C@H](OC(O)[C@H](O)[C@H]4O)CO)O[C@H](CO)[C@@H]3O)O)O[C@H](CO)[C@H]2O)NC(C)=O)O[C@H](CO)[C@H](O)[C@@H]1O FZIVHOUANIQOMU-YIHIYSSUSA-N 0.000 claims description 5
- CMQZRJBJDCVIEY-JEOLMMCMSA-N alpha-L-Fucp-(1->3)-[beta-D-Galp-(1->4)]-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-D-Glcp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](CO)O[C@@H](O[C@@H]2[C@H]([C@H](O[C@@H]3[C@H](OC(O)[C@H](O)[C@H]3O)CO)O[C@H](CO)[C@@H]2O)O)[C@@H]1NC(C)=O CMQZRJBJDCVIEY-JEOLMMCMSA-N 0.000 claims description 5
- DUKURNFHYQXCJG-JEOLMMCMSA-N alpha-L-Fucp-(1->4)-[beta-D-Galp-(1->3)]-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-D-Glcp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](NC(C)=O)[C@H](O[C@@H]2[C@H]([C@H](O[C@@H]3[C@H](OC(O)[C@H](O)[C@H]3O)CO)O[C@H](CO)[C@@H]2O)O)O[C@@H]1CO DUKURNFHYQXCJG-JEOLMMCMSA-N 0.000 claims description 5
- ODDPRQJTYDIWJU-OAUIKNEUSA-N beta-D-Galp-(1->3)-beta-D-Galp-(1->4)-beta-D-Glcp Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)O[C@H](CO)[C@@H]1O ODDPRQJTYDIWJU-OAUIKNEUSA-N 0.000 claims description 5
- 150000002402 hexoses Chemical class 0.000 claims description 5
- FZIVHOUANIQOMU-UHFFFAOYSA-N lacto-N-fucopentaose I Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(OC3C(C(OC4C(OC(O)C(O)C4O)CO)OC(CO)C3O)O)OC(CO)C2O)NC(C)=O)OC(CO)C(O)C1O FZIVHOUANIQOMU-UHFFFAOYSA-N 0.000 claims description 5
- FKADDOYBRRMBPP-UHFFFAOYSA-N lacto-N-fucopentaose II Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(C)=O)C(OC2C(C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C2O)O)OC1CO FKADDOYBRRMBPP-UHFFFAOYSA-N 0.000 claims description 5
- CMQZRJBJDCVIEY-UHFFFAOYSA-N lacto-N-fucopentaose III Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(O)C(O)C(CO)O2)O)C(CO)OC(OC2C(C(OC3C(OC(O)C(O)C3O)CO)OC(CO)C2O)O)C1NC(C)=O CMQZRJBJDCVIEY-UHFFFAOYSA-N 0.000 claims description 5
- 150000002972 pentoses Chemical class 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 4
- 239000002198 insoluble material Substances 0.000 claims description 4
- RQNFGIWYOACERD-OCQMRBNYSA-N alpha-L-Fucp-(1->4)-[alpha-L-Fucp-(1->2)-beta-D-Galp-(1->3)]-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-D-Glcp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](CO)O[C@@H](O[C@@H]3[C@H]([C@H](O[C@@H]4[C@H](OC(O)[C@H](O)[C@H]4O)CO)O[C@H](CO)[C@@H]3O)O)[C@@H]2NC(C)=O)O[C@H]2[C@H]([C@H](O)[C@H](O)[C@H](C)O2)O)O[C@H](CO)[C@H](O)[C@@H]1O RQNFGIWYOACERD-OCQMRBNYSA-N 0.000 claims description 3
- DMYPRRDPOMGEAK-XWDFSUOISA-N beta-D-Galp-(1->3)-[alpha-L-Fucp-(1->4)]-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-D-Glcp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O[C@H]4[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O4)O)[C@H](O[C@H]4[C@H]([C@H](O)[C@H](O)[C@H](C)O4)O)[C@@H](CO)O3)NC(C)=O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](CO)OC(O)[C@@H]1O DMYPRRDPOMGEAK-XWDFSUOISA-N 0.000 claims description 3
- 238000004255 ion exchange chromatography Methods 0.000 claims description 3
- RQNFGIWYOACERD-UHFFFAOYSA-N lacto-N-Difucosylhexaose I Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(CO)OC(OC3C(C(OC4C(OC(O)C(O)C4O)CO)OC(CO)C3O)O)C2NC(C)=O)OC2C(C(O)C(O)C(C)O2)O)OC(CO)C(O)C1O RQNFGIWYOACERD-UHFFFAOYSA-N 0.000 claims description 3
- OQIUPKPUOLIHHS-UHFFFAOYSA-N lacto-N-difucohexaose I Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(CO)OC(OC3C(C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C3O)O)C2NC(C)=O)OC2C(C(O)C(O)C(C)O2)O)OC(CO)C(O)C1O OQIUPKPUOLIHHS-UHFFFAOYSA-N 0.000 claims description 3
- DMYPRRDPOMGEAK-UHFFFAOYSA-N lacto-N-difucohexaose II Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(OC3C(C(OC4C(C(O)C(O)C(CO)O4)O)C(OC4C(C(O)C(O)C(C)O4)O)C(CO)O3)NC(C)=O)C(O)C(CO)O2)O)C(CO)OC(O)C1O DMYPRRDPOMGEAK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002195 soluble material Substances 0.000 claims 1
- 238000004977 Hueckel calculation Methods 0.000 abstract description 81
- 230000008569 process Effects 0.000 abstract description 23
- 235000013305 food Nutrition 0.000 abstract description 14
- 238000003786 synthesis reaction Methods 0.000 abstract description 12
- 239000007787 solid Substances 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 6
- 229910001385 heavy metal Inorganic materials 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 239000002002 slurry Substances 0.000 abstract description 2
- 238000004611 spectroscopical analysis Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 84
- 239000012528 membrane Substances 0.000 description 33
- 239000002245 particle Substances 0.000 description 28
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000000926 separation method Methods 0.000 description 17
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 16
- 239000003729 cation exchange resin Substances 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 12
- 238000011026 diafiltration Methods 0.000 description 12
- 239000008101 lactose Substances 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 150000002772 monosaccharides Chemical class 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 150000001720 carbohydrates Chemical class 0.000 description 8
- 235000014633 carbohydrates Nutrition 0.000 description 8
- 238000009826 distribution Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000009295 crossflow filtration Methods 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 238000011146 sterile filtration Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 238000000113 differential scanning calorimetry Methods 0.000 description 6
- 150000002016 disaccharides Chemical class 0.000 description 6
- 238000000634 powder X-ray diffraction Methods 0.000 description 6
- 230000008929 regeneration Effects 0.000 description 6
- 238000011069 regeneration method Methods 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 230000005526 G1 to G0 transition Effects 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 235000008504 concentrate Nutrition 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- LKOHREGGXUJGKC-UHFFFAOYSA-N Lactodifucotetraose Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(O)C(O)OC2CO)OC2C(C(O)C(O)C(C)O2)O)OC(CO)C(O)C1O LKOHREGGXUJGKC-UHFFFAOYSA-N 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- LKOHREGGXUJGKC-GXSKDVPZSA-N alpha-L-Fucp-(1->3)-[alpha-L-Fucp-(1->2)-beta-D-Galp-(1->4)]-beta-D-Glcp Chemical compound C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]2O[C@@H]2[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]2O)[C@@H](O)[C@H](O)[C@@H]1O LKOHREGGXUJGKC-GXSKDVPZSA-N 0.000 description 4
- 238000005341 cation exchange Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000002178 crystalline material Substances 0.000 description 4
- 239000002158 endotoxin Substances 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- 238000000108 ultra-filtration Methods 0.000 description 4
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 3
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 description 3
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 description 3
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 230000002210 biocatalytic effect Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000001186 cumulative effect Effects 0.000 description 3
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 230000007717 exclusion Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- 229930182830 galactose Natural products 0.000 description 3
- 238000001641 gel filtration chromatography Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 235000016709 nutrition Nutrition 0.000 description 3
- 230000035764 nutrition Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 description 2
- 102000051366 Glycosyltransferases Human genes 0.000 description 2
- 108700023372 Glycosyltransferases Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000003109 Karl Fischer titration Methods 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 108091034117 Oligonucleotide Proteins 0.000 description 2
- 239000003011 anion exchange membrane Substances 0.000 description 2
- 235000008452 baby food Nutrition 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 239000012228 culture supernatant Substances 0.000 description 2
- 235000013365 dairy product Nutrition 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000011033 desalting Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000011013 endotoxin removal Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000013542 high molecular weight contaminant Substances 0.000 description 2
- 239000012510 hollow fiber Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- RJTOFDPWCJDYFZ-UHFFFAOYSA-N lacto-N-triose Natural products CC(=O)NC1C(O)C(O)C(CO)OC1OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1O RJTOFDPWCJDYFZ-UHFFFAOYSA-N 0.000 description 2
- 239000013541 low molecular weight contaminant Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000001471 micro-filtration Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000004334 sorbic acid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- PJVXUVWGSCCGHT-ZPYZYFCMSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;(3s,4r,5r)-1,3,4,5,6-pentahydroxyhexan-2-one Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO PJVXUVWGSCCGHT-ZPYZYFCMSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 239000000592 Artificial Cell Substances 0.000 description 1
- 108010077805 Bacterial Proteins Proteins 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 108020004511 Recombinant DNA Proteins 0.000 description 1
- 239000005862 Whey Substances 0.000 description 1
- 102000007544 Whey Proteins Human genes 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- -1 certain HMOs Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004185 countercurrent chromatography Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000011038 discontinuous diafiltration by volume reduction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000012154 double-distilled water Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000011868 grain product Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- JCQLYHFGKNRPGE-FCVZTGTOSA-N lactulose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 JCQLYHFGKNRPGE-FCVZTGTOSA-N 0.000 description 1
- 229960000511 lactulose Drugs 0.000 description 1
- PFCRQPBOOFTZGQ-UHFFFAOYSA-N lactulose keto form Natural products OCC(=O)C(O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1O PFCRQPBOOFTZGQ-UHFFFAOYSA-N 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000003685 thermal hair damage Effects 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000000193 wide-angle powder X-ray diffraction Methods 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/15—Vitamins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/40—Complete food formulations for specific consumer groups or specific purposes, e.g. infant formula
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/702—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/18—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
- B01D15/1814—Recycling of the fraction to be distributed
- B01D15/1821—Simulated moving beds
- B01D15/185—Simulated moving beds characterised by the components to be separated
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction, e.g. ion-exchange, ion-pair, ion-suppression or ion-exclusion
- B01D15/361—Ion-exchange
- B01D15/362—Cation-exchange
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/42—Electrodialysis; Electro-osmosis ; Electro-ultrafiltration; Membrane capacitive deionization
- B01D61/422—Electrodialysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/16—Inorganic salts, minerals or trace elements
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/04—Sulfur, selenium or tellurium; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/06—Aluminium, calcium or magnesium; Compounds thereof, e.g. clay
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/18—Iodine; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/34—Copper; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/66—Microorganisms or materials therefrom
- A61K35/74—Bacteria
- A61K35/741—Probiotics
- A61K35/744—Lactic acid bacteria, e.g. enterococci, pediococci, lactococci, streptococci or leuconostocs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2315/00—Details relating to the membrane module operation
- B01D2315/16—Diafiltration
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nutrition Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Mycology (AREA)
- Biochemistry (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Water Supply & Treatment (AREA)
- Analytical Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Sustainable Development (AREA)
- Microbiology (AREA)
- Pediatric Medicine (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Urology & Nephrology (AREA)
- Nanotechnology (AREA)
- Hematology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13187369.7A EP2857410A1 (en) | 2013-10-04 | 2013-10-04 | Process for purification of 2´-fucosyllactose using simulated moving bed chromatography |
| EP13187369.7 | 2013-10-04 | ||
| PCT/EP2014/071145 WO2015049331A1 (en) | 2013-10-04 | 2014-10-02 | Process for purification of a neutral human milk oligosaccharide using simulated moving bed chromatography |
| CN201480054230.4A CN105814070A (zh) | 2013-10-04 | 2014-10-02 | 使用模拟移动床色谱纯化中性人乳寡糖的方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480054230.4A Division CN105814070A (zh) | 2013-10-04 | 2014-10-02 | 使用模拟移动床色谱纯化中性人乳寡糖的方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109705175A CN109705175A (zh) | 2019-05-03 |
| CN109705175B true CN109705175B (zh) | 2022-07-05 |
Family
ID=49293548
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811603666.0A Active CN109705175B (zh) | 2013-10-04 | 2014-10-02 | 使用模拟移动床色谱纯化中性人乳寡糖的方法 |
| CN201480054230.4A Withdrawn CN105814070A (zh) | 2013-10-04 | 2014-10-02 | 使用模拟移动床色谱纯化中性人乳寡糖的方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480054230.4A Withdrawn CN105814070A (zh) | 2013-10-04 | 2014-10-02 | 使用模拟移动床色谱纯化中性人乳寡糖的方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US10435427B2 (enExample) |
| EP (2) | EP2857410A1 (enExample) |
| JP (1) | JP6666243B2 (enExample) |
| KR (1) | KR102298281B1 (enExample) |
| CN (2) | CN109705175B (enExample) |
| BR (1) | BR112016007342B1 (enExample) |
| DK (1) | DK3063159T3 (enExample) |
| ES (1) | ES2868249T3 (enExample) |
| MX (2) | MX373919B (enExample) |
| PH (1) | PH12016500594B1 (enExample) |
| PL (1) | PL3063159T3 (enExample) |
| RU (1) | RU2685537C2 (enExample) |
| WO (1) | WO2015049331A1 (enExample) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2857410A1 (en) | 2013-10-04 | 2015-04-08 | Jennewein Biotechnologie GmbH | Process for purification of 2´-fucosyllactose using simulated moving bed chromatography |
| DK2896628T3 (en) | 2014-01-20 | 2019-01-14 | Jennewein Biotechnologie Gmbh | Process for Effective Purification of Neutral Milk Oligosaccharides (HMOs) from Microbial Fermentation |
| US10314852B2 (en) | 2014-10-24 | 2019-06-11 | Glycom A/S | Mixtures of HMOs |
| EP3390652B1 (en) | 2015-12-18 | 2024-12-04 | Glycom A/S | Fermentative production of oligosaccharides |
| US11312741B2 (en) | 2016-04-19 | 2022-04-26 | Glycom A/S | Separation of oligosaccharides from fermentation broth |
| WO2017221208A1 (en) | 2016-06-24 | 2017-12-28 | Glycom A/S | Compositions comprising hmos, their production and use for the prevention and/or treatment of viral and/or bacterial infections |
| KR101979608B1 (ko) * | 2017-04-17 | 2019-08-28 | 재단법인 탄소순환형 차세대 바이오매스 생산전환 기술연구단 | 푸코오스 분리방법 및 이를 위한 장치 |
| AU2018295414A1 (en) * | 2017-07-07 | 2020-01-16 | Societe Des Produits Nestle S.A. | Human milk fortifier |
| WO2019012461A1 (en) | 2017-07-12 | 2019-01-17 | Glycom A/S | AMORPHOUS MIXTURE COMPRISING A NEUTRAL MONO- OR OLIGOSACCHARIDE AND A NON-GLUCIDIC ACID COMPONENT |
| EP3450443A1 (en) * | 2017-08-29 | 2019-03-06 | Jennewein Biotechnologie GmbH | Process for purifying sialylated oligosaccharides |
| WO2019050321A1 (ko) * | 2017-09-07 | 2019-03-14 | (주)프로테옴텍 | 다수의 검사선을 구비한 크로마토그래피용 스트립, 이를 포함하는 진단 키트 및 다수의 경쟁적 반응 측정 단계를 포함하는 정성, 반정량, 정량 분석방법 |
| CN111164090A (zh) * | 2017-09-29 | 2020-05-15 | 菲仕兰坎皮纳荷兰公司 | 用于从微生物发酵纯化中性母乳寡糖(hmo)的方法 |
| EP3494805B1 (en) | 2017-12-08 | 2025-08-13 | Chr. Hansen HMO GmbH | Spray-dried tetrasaccharides |
| PL3494804T3 (pl) | 2017-12-08 | 2025-10-06 | Chr. Hansen HMO GmbH | Suszona rozpyłowo 3-fukozylolaktoza |
| EP3494807A1 (en) | 2017-12-11 | 2019-06-12 | Jennewein Biotechnologie GmbH | Spray-dried sialyllactose |
| ES3040419T3 (en) | 2017-12-08 | 2025-10-30 | Chr Hansen Hmo Gmbh | Spray-dried lacto-n-fucopentaose |
| CN111447845B (zh) * | 2017-12-08 | 2022-10-28 | 科汉森母乳低聚糖股份有限公司 | 喷雾干燥的唾液酸乳糖 |
| PL3524067T3 (pl) | 2018-02-08 | 2025-06-09 | Chr. Hansen HMO GmbH | Suszona rozpyłowo mieszanina oligosacharydów mleka ludzkiego |
| EP3546060A1 (en) * | 2018-03-27 | 2019-10-02 | DuPont Nutrition Biosciences ApS | Process for spray drying fucosyllactose solutions and related product compositions |
| WO2019160922A1 (en) * | 2018-02-19 | 2019-08-22 | Dupont Nutrition Biosciences Aps | Process for spray drying fucosyllactose solutions and related product compositions |
| KR20210006916A (ko) | 2018-05-07 | 2021-01-19 | 젠와인 바이오테크놀로지 게엠바하 | 미생물 발효에 의해 수득된 탄수화물로부터 락토-N-네오테트라오스 (LNnT)를 정제하기 위한 간단한 방법 |
| WO2019226431A1 (en) * | 2018-05-23 | 2019-11-28 | Dsm Ip Assets B.V. | Production of oligosaccharides |
| US20210298328A1 (en) * | 2018-08-08 | 2021-09-30 | Mars, Incoroprated | Pet food products comprising oligosaccharides and methods of use |
| AU2019362595B2 (en) | 2018-10-18 | 2024-12-19 | Basf Se | Crystalline form II of 2'-O-fucosyllactose, process for its preparation, nutritional, cosmetic or pharmaceutical formulation containing the same |
| EP3741770A1 (en) * | 2019-05-21 | 2020-11-25 | Jennewein Biotechnologie GmbH | Purification of oligosaccharides from a fermentation broth by using filtration |
| EP3750902A1 (en) * | 2019-06-14 | 2020-12-16 | Jennewein Biotechnologie GmbH | Process for the purification of lacto-n-neotetraose |
| WO2021011905A1 (en) * | 2019-07-18 | 2021-01-21 | The Regents Of The University Of California | Human milk oligosaccharides for control of dietary response and metabolic phenotype |
| MX2022002949A (es) | 2019-09-24 | 2022-04-06 | Prolacta Bioscience Inc | Composiciones y metodos para el tratamiento de enfermedades inflamatorias e inmunes. |
| CN110672756B (zh) * | 2019-11-07 | 2020-12-29 | 江南大学 | 一种奶粉中2’-岩藻糖基乳糖含量的检测方法 |
| CN115003681B (zh) * | 2020-01-29 | 2024-07-05 | 帝斯曼知识产权资产管理有限公司 | 用于回收和纯化人乳寡糖的方法 |
| KR20220155595A (ko) * | 2020-03-20 | 2022-11-23 | 글리콤 에이/에스 | 고체 hmo 생성물을 제공하는 방법, 및 이에 의해 수득된 고체 hmo 생성물 |
| WO2021250191A1 (en) * | 2020-06-12 | 2021-12-16 | Basf Se | Improved demineralization of fermentation broths and purification of fine chemicals such as oligosaccharides |
| IL300573A (en) | 2020-08-14 | 2023-04-01 | Prolacta Bioscience Inc | Breast milk oligosaccharide compositions for use with bacteriotherapy |
| CN112526022A (zh) * | 2020-11-27 | 2021-03-19 | 内蒙古伊利实业集团股份有限公司 | 一种乳中母乳低聚糖的检测方法 |
| JP2024502629A (ja) | 2021-01-12 | 2024-01-22 | プロラクタ バイオサイエンス,インコーポレイテッド | シンバイオティック治療レジメン |
| EP4418878A1 (en) * | 2021-10-18 | 2024-08-28 | DSM IP Assets B.V. | A method for providing an amorphous hmo product by drying |
| CN117003803A (zh) | 2022-05-07 | 2023-11-07 | 山东恒鲁生物科技有限公司 | 一种三糖的新晶型 |
| CN115873051B (zh) | 2022-05-17 | 2024-06-25 | 山东恒鲁生物科技有限公司 | 三糖的新晶型 |
| CN115073539B (zh) * | 2022-07-21 | 2023-06-16 | 南京工业大学 | 一种2’-岩藻糖基乳糖分离纯化的方法 |
| CN115260255B (zh) * | 2022-08-30 | 2024-06-28 | 南京工业大学 | 一种利用模拟移动床分离纯化2’-岩藻糖基乳糖的方法 |
| WO2024130119A2 (en) | 2022-12-16 | 2024-06-20 | Prolacta Bioscience, Inc. | Synbiotic compositions for short chain fatty acid production |
| CN115856151B (zh) * | 2022-12-27 | 2025-08-12 | 深圳市中科朗健生物技术有限公司 | 一种同时测定多种人乳低聚糖的高效液相色谱检测方法 |
| CN115838390A (zh) * | 2022-12-30 | 2023-03-24 | 保龄宝生物股份有限公司 | 一种利用三组分色谱分离技术制备高含量2′-岩藻糖基乳糖的方法 |
| WO2024165630A1 (en) * | 2023-02-07 | 2024-08-15 | N.V. Nutricia | Nutritional composition with improved segregation resistance |
| CN118805902A (zh) * | 2023-04-19 | 2024-10-22 | 科·汉森有限公司 | 母乳低聚糖 |
| WO2025056571A1 (en) | 2023-09-12 | 2025-03-20 | Frieslandcampina Nederland B.V. | Milk extracellular vesicle enrichment process |
| CN117089503B (zh) | 2023-10-17 | 2024-01-02 | 保龄宝生物股份有限公司 | 一种大肠杆菌k-12 mg1655 blbyzt6及其应用 |
| WO2025149372A1 (en) | 2024-01-09 | 2025-07-17 | Frieslandcampina Nederland B.V. | Milk extracellular vesicle enrichment process using peg |
| CN119192253B (zh) * | 2024-09-06 | 2025-10-21 | 虹摹生物科技(上海)有限公司 | 一种岩藻糖基乳糖及其纯化方法 |
| CN120847064B (zh) * | 2025-09-23 | 2025-12-05 | 吉林省科技创新研究院有限公司 | 一种液体中微量可见异物分析鉴定方法 |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1222869A (zh) * | 1996-05-24 | 1999-07-14 | 库尔特公司 | 用色谱模拟移动床方法分离溶液的方法 |
| CN1242776A (zh) * | 1996-10-10 | 2000-01-26 | 尼澳斯技术股份有限公司 | 用超滤、反渗透和纳滤纯化糖类 |
| CN101367844A (zh) * | 2008-09-17 | 2009-02-18 | 无锡绿色分离应用技术研究所有限公司 | 一种从阿拉伯胶水解液中提取阿拉伯糖的方法 |
| CN101831475A (zh) * | 2010-03-24 | 2010-09-15 | 方煜宇 | 一种生产高纯度低聚半乳糖的方法 |
| CN102459295A (zh) * | 2009-04-07 | 2012-05-16 | 格礼卡姆股份公司 | 2’-o-岩藻糖基乳糖的合成 |
| CN102676604A (zh) * | 2011-03-08 | 2012-09-19 | 保龄宝生物股份有限公司 | 一种连续模拟移动床色谱分离制备高纯度低聚半乳糖的方法 |
| WO2012158517A1 (en) * | 2011-05-13 | 2012-11-22 | Glycosyn LLC | The use of purified 2'-fucosyllactose, 3-fucosyllactose and lactodifucotetraose as prebiotics |
| WO2012156897A1 (en) * | 2011-05-13 | 2012-11-22 | Glycom A/S | METHOD FOR GENERATING HUMAN MILK OLIGOSACCHARIDES (HMOs) OR PRECURSORS THEREOF |
| WO2012156898A1 (en) * | 2011-05-13 | 2012-11-22 | Glycom A/S | DIVERSIFICATION OF HUMAN MILK OLIGOSACCHARIDES (HMOs) OR PRECURSORS THEREOF |
| CN103025749A (zh) * | 2010-06-01 | 2013-04-03 | 格礼卡姆股份公司 | 2’-o-岩藻糖基乳糖的多晶型物及其制备 |
| CN103113422A (zh) * | 2013-02-06 | 2013-05-22 | 广西轻工业科学技术研究院 | 一种用模拟流动床分离精制高纯度l-阿拉伯糖、d-木糖的方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0779800B2 (ja) | 1986-01-23 | 1995-08-30 | オムロン株式会社 | 電子血圧計 |
| JPH0639206B2 (ja) | 1988-04-18 | 1994-05-25 | 田村プラスチック製品株式会社 | ルーフバイザーの取り付け方法 |
| JPH02286695A (ja) | 1989-04-28 | 1990-11-26 | Sumitomo Heavy Ind Ltd | オリゴ糖の分離方法 |
| NZ240002A (en) * | 1991-09-30 | 1993-11-25 | Lactose Co Of Nz Ltd | Method of producing a dry powder containing lactose and "oligosaccharides" |
| JPH0779927B2 (ja) | 1992-05-22 | 1995-08-30 | 川崎重工業株式会社 | 擬似移動床式液体クロマトオリゴ糖分離装置 |
| JPH06253879A (ja) * | 1993-03-01 | 1994-09-13 | Snow Brand Milk Prod Co Ltd | グルクロン酸結合オリゴ糖の分離方法 |
| DE4326665C2 (de) * | 1993-08-09 | 1995-07-13 | Biotest Pharma Gmbh | Verfahren zur Sterilfiltration von Milch |
| JP3368389B2 (ja) | 1993-09-14 | 2003-01-20 | 雪印乳業株式会社 | シアル酸含有オリゴ糖の分離方法 |
| DK0931097T3 (da) | 1996-10-10 | 2006-01-16 | Neose Technologies Inc | Kulhydratoprensning ved anvendelse af omvendt osmose og nanofiltrering |
| EP1531832B1 (en) * | 2002-06-28 | 2009-04-15 | Glykos Finland Oy | Therapeutic compositions for use in prophylaxis or treatment of diarrheas |
| EP1634599A1 (en) * | 2004-08-20 | 2006-03-15 | N.V. Nutricia | Iimmune stimulatory infant nutrition |
| JP5184768B2 (ja) | 2006-09-05 | 2013-04-17 | 株式会社林原 | トレハロース高含有糖液の回収方法並びに結晶トレハロースの製造方法 |
| EP2293677B1 (en) | 2008-06-13 | 2017-11-15 | N.V. Nutricia | Nutritional composition for infants delivered via caesarean section |
| ES2660698T3 (es) * | 2009-06-08 | 2018-03-23 | Jennewein Biotechnologie Gmbh | Síntesis de HMO |
| EP2465507A1 (en) | 2010-11-23 | 2012-06-20 | Nestec S.A. | Oligosaccharide composition for treating skin diseases |
| DE12746649T1 (de) | 2011-02-16 | 2016-09-29 | Glycosyn LLC | Biosynthese menschlicher milcholigosaccaride in manipulierten Bakterien |
| EP2526784A1 (en) * | 2011-05-24 | 2012-11-28 | Nestec S.A. | Milk oligosaccharide-galactooligosaccharide composition for infant formula containing the soluble oligosaccharide fraction present in milk, and having a low level of monosaccharides, and a process to produce the composition |
| DE202013012827U1 (de) * | 2012-06-14 | 2020-02-13 | Glycom A/S | Verbesserung der Stabilität und Reinheit sowie Erhöhung der Bioverfügbarkeit von menschlichen Milch-Oligosacchariden oder Vorläufern oder Mischungen davon |
| EP2857410A1 (en) | 2013-10-04 | 2015-04-08 | Jennewein Biotechnologie GmbH | Process for purification of 2´-fucosyllactose using simulated moving bed chromatography |
-
2013
- 2013-10-04 EP EP13187369.7A patent/EP2857410A1/en active Pending
-
2014
- 2014-10-02 CN CN201811603666.0A patent/CN109705175B/zh active Active
- 2014-10-02 CN CN201480054230.4A patent/CN105814070A/zh not_active Withdrawn
- 2014-10-02 PL PL14777665T patent/PL3063159T3/pl unknown
- 2014-10-02 EP EP14777665.2A patent/EP3063159B1/en not_active Revoked
- 2014-10-02 BR BR112016007342-8A patent/BR112016007342B1/pt active IP Right Grant
- 2014-10-02 PH PH1/2016/500594A patent/PH12016500594B1/en unknown
- 2014-10-02 US US15/027,047 patent/US10435427B2/en active Active
- 2014-10-02 DK DK14777665.2T patent/DK3063159T3/da active
- 2014-10-02 MX MX2016004288A patent/MX373919B/es active IP Right Grant
- 2014-10-02 RU RU2016109548A patent/RU2685537C2/ru active
- 2014-10-02 ES ES14777665T patent/ES2868249T3/es active Active
- 2014-10-02 KR KR1020167008862A patent/KR102298281B1/ko active Active
- 2014-10-02 WO PCT/EP2014/071145 patent/WO2015049331A1/en not_active Ceased
- 2014-10-02 JP JP2016520025A patent/JP6666243B2/ja active Active
-
2016
- 2016-04-01 MX MX2020004844A patent/MX2020004844A/es unknown
-
2019
- 2019-06-13 US US16/440,100 patent/US11168105B2/en active Active
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1222869A (zh) * | 1996-05-24 | 1999-07-14 | 库尔特公司 | 用色谱模拟移动床方法分离溶液的方法 |
| CN1242776A (zh) * | 1996-10-10 | 2000-01-26 | 尼澳斯技术股份有限公司 | 用超滤、反渗透和纳滤纯化糖类 |
| CN101367844A (zh) * | 2008-09-17 | 2009-02-18 | 无锡绿色分离应用技术研究所有限公司 | 一种从阿拉伯胶水解液中提取阿拉伯糖的方法 |
| CN102459295A (zh) * | 2009-04-07 | 2012-05-16 | 格礼卡姆股份公司 | 2’-o-岩藻糖基乳糖的合成 |
| CN101831475A (zh) * | 2010-03-24 | 2010-09-15 | 方煜宇 | 一种生产高纯度低聚半乳糖的方法 |
| CN103025749A (zh) * | 2010-06-01 | 2013-04-03 | 格礼卡姆股份公司 | 2’-o-岩藻糖基乳糖的多晶型物及其制备 |
| CN102676604A (zh) * | 2011-03-08 | 2012-09-19 | 保龄宝生物股份有限公司 | 一种连续模拟移动床色谱分离制备高纯度低聚半乳糖的方法 |
| WO2012158517A1 (en) * | 2011-05-13 | 2012-11-22 | Glycosyn LLC | The use of purified 2'-fucosyllactose, 3-fucosyllactose and lactodifucotetraose as prebiotics |
| WO2012156897A1 (en) * | 2011-05-13 | 2012-11-22 | Glycom A/S | METHOD FOR GENERATING HUMAN MILK OLIGOSACCHARIDES (HMOs) OR PRECURSORS THEREOF |
| WO2012156898A1 (en) * | 2011-05-13 | 2012-11-22 | Glycom A/S | DIVERSIFICATION OF HUMAN MILK OLIGOSACCHARIDES (HMOs) OR PRECURSORS THEREOF |
| CN103113422A (zh) * | 2013-02-06 | 2013-05-22 | 广西轻工业科学技术研究院 | 一种用模拟流动床分离精制高纯度l-阿拉伯糖、d-木糖的方法 |
Non-Patent Citations (1)
| Title |
|---|
| Separation of lactose from human milk oligosaccharides with simulated moving bed chromatography;Andreas Geisser et al.;《Journal of Chromatography A》;20051021;第1092卷(第1期);第17-23页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109705175A (zh) | 2019-05-03 |
| BR112016007342A2 (pt) | 2017-08-01 |
| JP6666243B2 (ja) | 2020-03-13 |
| US10435427B2 (en) | 2019-10-08 |
| JP2016535724A (ja) | 2016-11-17 |
| US11168105B2 (en) | 2021-11-09 |
| ES2868249T3 (es) | 2021-10-21 |
| RU2685537C2 (ru) | 2019-04-22 |
| KR20160090791A (ko) | 2016-08-01 |
| EP2857410A1 (en) | 2015-04-08 |
| CN105814070A (zh) | 2016-07-27 |
| MX2016004288A (es) | 2017-01-18 |
| US20190292211A1 (en) | 2019-09-26 |
| MX2020004844A (es) | 2020-10-20 |
| MX373919B (es) | 2020-07-13 |
| DK3063159T3 (da) | 2021-05-10 |
| PL3063159T3 (pl) | 2021-07-19 |
| PH12016500594A1 (en) | 2016-06-13 |
| EP3063159B1 (en) | 2021-04-07 |
| RU2016109548A (ru) | 2017-11-09 |
| US20160237104A1 (en) | 2016-08-18 |
| EP3063159A1 (en) | 2016-09-07 |
| KR102298281B1 (ko) | 2021-09-07 |
| PH12016500594B1 (en) | 2023-10-20 |
| RU2016109548A3 (enExample) | 2018-06-25 |
| WO2015049331A1 (en) | 2015-04-09 |
| BR112016007342B1 (pt) | 2020-11-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109705175B (zh) | 使用模拟移动床色谱纯化中性人乳寡糖的方法 | |
| US20240026403A1 (en) | Process for the Purification of L-Fucose from a Fermentation Broth | |
| KR102788471B1 (ko) | 시알릴화 올리고당의 정제 방법 | |
| HK40008041B (en) | Process for purification of a neutral human milk oligosaccharide using simulated moving bed chromatography | |
| HK40008041A (en) | Process for purification of a neutral human milk oligosaccharide using simulated moving bed chromatography | |
| AU2018267652B2 (en) | Process for Purification of a Neutral Human Milk Oligosaccharide Using Simulated Moving Bed Chromotography | |
| RU2799091C2 (ru) | Способ очистки сиалилированных олигосахаридов | |
| AU2014331091A1 (en) | Process for purification of a neutral human milk oligosaccharide using simulated moving bed chromatography | |
| HK40019083A (en) | Process for purifying sialylated oligosaccharides | |
| CN119504889A (zh) | 一种唾液酸化寡糖的纯化方法 | |
| HK40026259A (zh) | 喷雾干燥的人乳低聚糖混合物 | |
| HK40024507A (en) | Spray-dried lacto-n-fucopentaose | |
| HK40023985A (en) | Process for the purification of l-fucose from a fermentation broth | |
| HK40024597A (en) | Spray-dried sialyllactose | |
| HK40024600A (en) | Spray-dried tetrasaccharides | |
| HK40026258A (en) | Spray-dried 3-fucosyllactose |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: DE Ref document number: 40008041 Country of ref document: HK |
|
| CB02 | Change of applicant information | ||
| CB02 | Change of applicant information |
Address after: Bright Bach, Rhine, Germany Applicant after: Kohansen HMO Co.,Ltd. Address before: Bright Bach, Rhine, Germany Applicant before: Jennewein Biotechnologie GmbH |
|
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CP03 | Change of name, title or address | ||
| CP03 | Change of name, title or address |
Address after: Reinbrechtbach, Germany Patentee after: Kohansen breast milk oligosaccharides Co.,Ltd. Address before: Bright Bach, Rhine, Germany Patentee before: Kohansen HMO Co.,Ltd. |