DE2530861C3 - Verfahren zur Herstellung von 2-Keto-L-gulonsäure und deren Salzen - Google Patents
Verfahren zur Herstellung von 2-Keto-L-gulonsäure und deren SalzenInfo
- Publication number
- DE2530861C3 DE2530861C3 DE2530861A DE2530861A DE2530861C3 DE 2530861 C3 DE2530861 C3 DE 2530861C3 DE 2530861 A DE2530861 A DE 2530861A DE 2530861 A DE2530861 A DE 2530861A DE 2530861 C3 DE2530861 C3 DE 2530861C3
- Authority
- DE
- Germany
- Prior art keywords
- growth
- strain
- acid
- keto
- atcc
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 47
- VBUYCZFBVCCYFD-NUNKFHFFSA-N 2-dehydro-L-idonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)C(=O)C(O)=O VBUYCZFBVCCYFD-NUNKFHFFSA-N 0.000 title claims description 38
- VBUYCZFBVCCYFD-UHFFFAOYSA-N D-arabino-2-Hexulosonic acid Natural products OCC(O)C(O)C(O)C(=O)C(O)=O VBUYCZFBVCCYFD-UHFFFAOYSA-N 0.000 title claims description 38
- 230000008569 process Effects 0.000 title claims description 16
- 150000003839 salts Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 7
- 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 claims description 47
- 244000005700 microbiome Species 0.000 claims description 23
- 241000186146 Brevibacterium Species 0.000 claims description 21
- RXMWXENJQAINCC-DMTCNVIQSA-N 2,5-didehydro-D-gluconic acid Chemical compound OCC(=O)[C@@H](O)[C@H](O)C(=O)C(O)=O RXMWXENJQAINCC-DMTCNVIQSA-N 0.000 claims description 18
- RXMWXENJQAINCC-UHFFFAOYSA-N 2,5-diketo-D-gluconic acid Natural products OCC(=O)C(O)C(O)C(=O)C(O)=O RXMWXENJQAINCC-UHFFFAOYSA-N 0.000 claims description 18
- 241000186249 Corynebacterium sp. Species 0.000 claims description 17
- 241000589236 Gluconobacter Species 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 10
- 241000589220 Acetobacter Species 0.000 claims description 9
- 241000186312 Brevibacterium sp. Species 0.000 claims description 7
- 102000004190 Enzymes Human genes 0.000 claims description 7
- 108090000790 Enzymes Proteins 0.000 claims description 7
- 241000589232 Gluconobacter oxydans Species 0.000 claims description 6
- 241000186216 Corynebacterium Species 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 241000203815 Microbacterium testaceum Species 0.000 claims 1
- 230000012010 growth Effects 0.000 description 130
- 230000015572 biosynthetic process Effects 0.000 description 94
- 235000010633 broth Nutrition 0.000 description 89
- 239000002609 medium Substances 0.000 description 76
- 239000002253 acid Substances 0.000 description 61
- 229920001817 Agar Polymers 0.000 description 45
- 239000008272 agar Substances 0.000 description 45
- 235000013372 meat Nutrition 0.000 description 44
- 238000012360 testing method Methods 0.000 description 39
- 210000004027 cell Anatomy 0.000 description 38
- 241000831652 Salinivibrio sharmensis Species 0.000 description 28
- 239000007789 gas Substances 0.000 description 26
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- 238000011534 incubation Methods 0.000 description 22
- VBUYCZFBVCCYFD-JJYYJPOSSA-N 2-dehydro-D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)C(O)=O VBUYCZFBVCCYFD-JJYYJPOSSA-N 0.000 description 20
- 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 19
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 19
- 239000008101 lactose Substances 0.000 description 19
- 229940088594 vitamin Drugs 0.000 description 19
- 239000011782 vitamin Substances 0.000 description 19
- 235000013343 vitamin Nutrition 0.000 description 19
- 229930003231 vitamin Natural products 0.000 description 19
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 18
- 150000003722 vitamin derivatives Chemical class 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 16
- 235000015097 nutrients Nutrition 0.000 description 16
- 229940041514 candida albicans extract Drugs 0.000 description 15
- 239000012138 yeast extract Substances 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- 229920002472 Starch Polymers 0.000 description 14
- 238000011084 recovery Methods 0.000 description 14
- 239000008107 starch Substances 0.000 description 14
- 235000019698 starch Nutrition 0.000 description 14
- 229910002651 NO3 Inorganic materials 0.000 description 13
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 230000004151 fermentation Effects 0.000 description 12
- 235000011187 glycerol Nutrition 0.000 description 12
- 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 11
- 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 11
- 238000000855 fermentation Methods 0.000 description 11
- 229950006191 gluconic acid Drugs 0.000 description 11
- 239000008103 glucose Substances 0.000 description 11
- 235000013336 milk Nutrition 0.000 description 11
- 239000008267 milk Substances 0.000 description 11
- 210000004080 milk Anatomy 0.000 description 11
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 10
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 10
- SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 229930006000 Sucrose Natural products 0.000 description 10
- 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 10
- 235000010355 mannitol Nutrition 0.000 description 10
- 239000012188 paraffin wax Substances 0.000 description 10
- 239000013049 sediment Substances 0.000 description 10
- 229960002920 sorbitol Drugs 0.000 description 10
- 239000005720 sucrose Substances 0.000 description 10
- 235000000346 sugar Nutrition 0.000 description 10
- 150000008163 sugars Chemical class 0.000 description 10
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 9
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 9
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 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 9
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 8
- 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 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 8
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 8
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 8
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 8
- 108010010803 Gelatin Proteins 0.000 description 8
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 8
- 239000001888 Peptone Substances 0.000 description 8
- 108010080698 Peptones Proteins 0.000 description 8
- 244000061456 Solanum tuberosum Species 0.000 description 8
- 235000002595 Solanum tuberosum Nutrition 0.000 description 8
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products 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](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 8
- 108010046334 Urease Proteins 0.000 description 8
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose 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](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 8
- 230000032823 cell division Effects 0.000 description 8
- 239000001913 cellulose Substances 0.000 description 8
- 235000010980 cellulose Nutrition 0.000 description 8
- 229920002678 cellulose Polymers 0.000 description 8
- 239000008273 gelatin Substances 0.000 description 8
- 229920000159 gelatin Polymers 0.000 description 8
- 235000019322 gelatine Nutrition 0.000 description 8
- 235000011852 gelatine desserts Nutrition 0.000 description 8
- 235000012208 gluconic acid Nutrition 0.000 description 8
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 8
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 8
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 8
- CEQFOVLGLXCDCX-WUKNDPDISA-N methyl red Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-WUKNDPDISA-N 0.000 description 8
- 230000004899 motility Effects 0.000 description 8
- 235000019319 peptone Nutrition 0.000 description 8
- 230000001766 physiological effect Effects 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- 238000011218 seed culture Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 230000001954 sterilising effect Effects 0.000 description 8
- 238000004659 sterilization and disinfection Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CJVYYDCBKKKIPD-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetramethylbenzene-1,2-diamine Chemical compound CN(C)C1=CC=CC=C1N(C)C CJVYYDCBKKKIPD-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 7
- 102000016938 Catalase Human genes 0.000 description 7
- 108010053835 Catalase Proteins 0.000 description 7
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 7
- 102000004316 Oxidoreductases Human genes 0.000 description 7
- 108090000854 Oxidoreductases Proteins 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 7
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 7
- 229960000907 methylthioninium chloride Drugs 0.000 description 7
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 7
- 239000008108 microcrystalline cellulose Substances 0.000 description 7
- 229940016286 microcrystalline cellulose Drugs 0.000 description 7
- 230000028070 sporulation Effects 0.000 description 7
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 6
- 229960000367 inositol Drugs 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 210000003495 flagella Anatomy 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 5
- 235000019796 monopotassium phosphate Nutrition 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000005345 coagulation Methods 0.000 description 4
- 230000015271 coagulation Effects 0.000 description 4
- 239000001963 growth medium Substances 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 235000019248 orcein Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 244000303040 Glycyrrhiza glabra Species 0.000 description 3
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 3
- 238000003794 Gram staining Methods 0.000 description 3
- -1 L-raffinose Chemical compound 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 description 3
- 235000015278 beef Nutrition 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 229960005150 glycerol Drugs 0.000 description 3
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 229960001375 lactose Drugs 0.000 description 3
- 235000011477 liquorice Nutrition 0.000 description 3
- 238000004816 paper chromatography Methods 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 230000002250 progressing effect Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000007480 spreading Effects 0.000 description 3
- 238000003892 spreading Methods 0.000 description 3
- 238000009633 stab culture Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002211 L-ascorbic acid Substances 0.000 description 2
- 235000000069 L-ascorbic acid Nutrition 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
- 230000001488 breeding effect Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 231100000219 mutagenic Toxicity 0.000 description 2
- 230000003505 mutagenic effect Effects 0.000 description 2
- 239000011591 potassium Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 230000000284 resting effect Effects 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- 229940074410 trehalose Drugs 0.000 description 2
- CDAISMWEOUEBRE-LKPKBOIGSA-N 1D-chiro-inositol Chemical compound O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O CDAISMWEOUEBRE-LKPKBOIGSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- IZSRJDGCGRAUAR-MROZADKFSA-N 5-dehydro-D-gluconic acid Chemical compound OCC(=O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O IZSRJDGCGRAUAR-MROZADKFSA-N 0.000 description 1
- GMVPRGQOIOIIMI-DODZYUBVSA-N 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DODZYUBVSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 125000002353 D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 241000131747 Exiguobacterium acetylicum Species 0.000 description 1
- 108010068370 Glutens Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920001202 Inulin Polymers 0.000 description 1
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 description 1
- RGHNJXZEOKUKBD-QTBDOELSSA-N L-gulonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-QTBDOELSSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- NGFMICBWJRZIBI-JZRPKSSGSA-N Salicin Natural products O([C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O1)c1c(CO)cccc1 NGFMICBWJRZIBI-JZRPKSSGSA-N 0.000 description 1
- 235000019764 Soybean Meal Nutrition 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- NGFMICBWJRZIBI-UHFFFAOYSA-N alpha-salicin Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UHFFFAOYSA-N 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003851 biochemical process Effects 0.000 description 1
- UBJLBNGSWJBOGI-UHFFFAOYSA-N bis(3-fluorophenyl)methanone Chemical compound FC1=CC=CC(C(=O)C=2C=C(F)C=CC=2)=C1 UBJLBNGSWJBOGI-UHFFFAOYSA-N 0.000 description 1
- 239000001058 brown pigment Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Chemical class 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 210000001822 immobilized cell Anatomy 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 1
- 229940029339 inulin Drugs 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011777 magnesium Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229960001855 mannitol Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000013048 microbiological method Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- KELXKDDAALYTDI-BTVCFUMJSA-N nitric acid;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound O[N+]([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O KELXKDDAALYTDI-BTVCFUMJSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- NGFMICBWJRZIBI-UJPOAAIJSA-N salicin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UJPOAAIJSA-N 0.000 description 1
- 229940120668 salicin Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
- C07H7/027—Keto-aldonic acids
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/58—Aldonic, ketoaldonic or saccharic acids
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/58—Aldonic, ketoaldonic or saccharic acids
- C12P7/60—2-Ketogulonic acid
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/823—Acetobacter
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/84—Brevibacterium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/843—Corynebacterium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49109314A JPS5135485A (en) | 1974-09-20 | 1974-09-20 | 22 keto ll guronsan no seizohoho |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2530861A1 DE2530861A1 (de) | 1976-04-01 |
| DE2530861B2 DE2530861B2 (de) | 1980-03-27 |
| DE2530861C3 true DE2530861C3 (de) | 1980-11-20 |
Family
ID=14507056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2530861A Expired DE2530861C3 (de) | 1974-09-20 | 1975-07-10 | Verfahren zur Herstellung von 2-Keto-L-gulonsäure und deren Salzen |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3998697A (enExample) |
| JP (1) | JPS5135485A (enExample) |
| AU (1) | AU496804B2 (enExample) |
| BR (1) | BR7506071A (enExample) |
| CA (1) | CA1043283A (enExample) |
| CH (1) | CH612440A5 (enExample) |
| DE (1) | DE2530861C3 (enExample) |
| FR (1) | FR2285456A1 (enExample) |
| GB (1) | GB1454249A (enExample) |
| IT (1) | IT1050602B (enExample) |
| NL (1) | NL169899C (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7809345L (sv) * | 1977-11-18 | 1979-05-19 | Pfizer | Sett att framstella 2,5-diketoglukonsyra |
| US4263402A (en) * | 1979-09-28 | 1981-04-21 | Pfizer Inc. | Process for producing 2,5-diketogluconic |
| US4316960A (en) * | 1979-09-28 | 1982-02-23 | Pfizer Inc. | Preparation of 2,5-diketogluconic acid |
| US4245049A (en) * | 1980-01-21 | 1981-01-13 | Pfizer Inc. | Preparation of 2-keto-L-gulonic acid |
| JPS6041596B2 (ja) * | 1980-08-14 | 1985-09-18 | 塩野義製薬株式会社 | 2,5−ジケト−d−グルコン酸の製造方法 |
| US5234819A (en) * | 1980-08-14 | 1993-08-10 | Shiongi & Co., Ltd. | Method for preparing 2,5-diketo-D-gluconic acid |
| JPS5783559A (en) * | 1980-11-11 | 1982-05-25 | Shinto Paint Co Ltd | Resin composition for water-based coating |
| JPS58162298A (ja) * | 1982-03-05 | 1983-09-26 | Shionogi & Co Ltd | 2−ケト−l−グロン酸の製造方法 |
| US4543331A (en) * | 1982-03-05 | 1985-09-24 | Shionogi & Co., Ltd. | Fermentative or enzymatic production of 2-keto-L-gulonic acid |
| US5004690A (en) * | 1983-06-28 | 1991-04-02 | Genetech, Inc. | Ascorbic acid intermediates and process enzymes |
| JPS60118186A (ja) * | 1983-11-17 | 1985-06-25 | Shionogi & Co Ltd | 2・5−ジケト−d−グルコン酸リダクタ−ゼ |
| US4935359A (en) * | 1987-02-07 | 1990-06-19 | Institute Of Microbiology | Fermentation process |
| DK173507B1 (da) * | 1988-09-30 | 2001-01-15 | Hoffmann La Roche | Fremgangsmåde til fremstilling af 2-keto-L-gulonsyre |
| US5376544A (en) * | 1992-09-08 | 1994-12-27 | Rutgers The State University Of New Jersey | Enzymes for the production of 2-keto-L-gulonic acid |
| US5437989A (en) * | 1992-12-30 | 1995-08-01 | Hoffmann-La Roche Inc. | Alcohol/aldehyde dehydrogenase from Gluconobacter oxydans DSM 4025 FERM BP-3812 |
| US5795761A (en) * | 1996-01-11 | 1998-08-18 | Rutgers, The State University Of New Jersey | Mutants of 2,5-diketo-D-gluconic acid (2,5-DKG) reductase A |
| US7256027B1 (en) | 1999-06-15 | 2007-08-14 | Rutgers, The State University Of New Jersey | Enzymes for the production of 2-keto-L-gulonic acid |
| US6387654B1 (en) | 2000-05-04 | 2002-05-14 | Archer-Daniels-Midland Company | Bacterial strains and fermentation processes for the production of 2-keto-l-gulonic acid |
| ATE526397T1 (de) | 2003-07-30 | 2011-10-15 | Genencor Int | Multimere oxidoreduktasen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2948659A (en) * | 1954-08-10 | 1960-08-09 | Pfizer & Co C | Synthesis of 2-keto-l-gulonic acid |
| US3907639A (en) * | 1972-08-31 | 1975-09-23 | Hoffmann La Roche | Method for producing 2-keto-L-gulonic acid |
-
1974
- 1974-09-20 JP JP49109314A patent/JPS5135485A/ja active Granted
-
1975
- 1975-04-21 US US05/569,852 patent/US3998697A/en not_active Expired - Lifetime
- 1975-06-03 CA CA228,404A patent/CA1043283A/en not_active Expired
- 1975-06-04 AU AU81856/75A patent/AU496804B2/en not_active Expired
- 1975-06-12 GB GB2525575A patent/GB1454249A/en not_active Expired
- 1975-06-30 FR FR7520522A patent/FR2285456A1/fr active Granted
- 1975-07-10 DE DE2530861A patent/DE2530861C3/de not_active Expired
- 1975-08-06 CH CH1026275A patent/CH612440A5/xx not_active IP Right Cessation
- 1975-09-17 IT IT69320/75A patent/IT1050602B/it active
- 1975-09-19 NL NLAANVRAGE7511128,A patent/NL169899C/xx not_active IP Right Cessation
- 1975-09-19 BR BR7506071*A patent/BR7506071A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3998697A (en) | 1976-12-21 |
| GB1454249A (en) | 1976-11-03 |
| NL169899C (nl) | 1982-09-01 |
| CH612440A5 (enExample) | 1979-07-31 |
| AU496804B2 (en) | 1978-11-02 |
| AU8185675A (en) | 1976-12-09 |
| NL7511128A (nl) | 1976-03-23 |
| FR2285456A1 (fr) | 1976-04-16 |
| CA1043283A (en) | 1978-11-28 |
| JPS5135485A (en) | 1976-03-25 |
| IT1050602B (it) | 1981-03-20 |
| DE2530861A1 (de) | 1976-04-01 |
| DE2530861B2 (de) | 1980-03-27 |
| NL169899B (nl) | 1982-04-01 |
| BR7506071A (pt) | 1976-08-03 |
| FR2285456B1 (enExample) | 1977-07-08 |
| JPS5419468B2 (enExample) | 1979-07-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2530861C3 (de) | Verfahren zur Herstellung von 2-Keto-L-gulonsäure und deren Salzen | |
| DE3882242T2 (de) | Fermentationsverfahren zur Herstellung von 2-Keto-L-Gulonsäuren. | |
| DE2413963C3 (de) | Verfahren zur Herstellung von 2-Keto-L-gulonsäure und deren Salzen auf mikrobiologischem Wege | |
| DE68915692T2 (de) | Fermentationsverfahren zur Herstellung von 2-Keto-L-Gulonsäure. | |
| DE602004008875T2 (de) | Herstellung von milchsäure aus einem pentose-enthaltenden substrat | |
| HU188073B (en) | Process for the preparation of 2,5-diketo-d-gluconic acid | |
| US3959076A (en) | Process for producing 2-keto-L-gulonic acid | |
| DE2400323C2 (de) | Neue Glucose-Isomerase und ihre Herstellung | |
| DE2634187A1 (de) | Verfahren zur maximalen steigerung des wachstums und der nikotinabbauaktivitaet von mikroorganismen | |
| DE1767653A1 (de) | Verfahren zur Erzeugung von Isoamylase | |
| DE2402217C3 (de) | Verfahren zur Herstellung von Proteinmaterial | |
| CH616706A5 (enExample) | ||
| Enebo | On Three Bacteria Connected with Thermophilic Cellulose Fermentation. | |
| DE2619311A1 (de) | Verfahren zur herstellung von l(+)weinsaeure | |
| DE2164018C3 (de) | Verfahren zur biotechnischen Her stellung von Uncase | |
| DE2702417A1 (de) | Neuer glyko-hydrolasen-inhibitor und dessen herstellung durch kultur eines streptomyces | |
| DE2363285A1 (de) | Verfahren zur herstellung von lapfelsaeure durch mikrobiologische fermentation und mittel zur durchfuehrung des verfahrens | |
| DE60006434T2 (de) | Mikrobielle Umwandlung von 2-Methylquinoxalin | |
| DE2850467A1 (de) | Verfahren zur gewinnung von moranolin | |
| DE2554407A1 (de) | Herstellung thermostabiler lactase | |
| DE2757877C3 (de) | Herstellung von Biomassen | |
| DE2456139A1 (de) | Neues verfahren zur herstellung des antibiotikums 20.798 r.p. | |
| DE2605921C3 (de) | Verfahren zur enzymatischen Herstellung von L-Weinsäure aus cis-Epoxybernsteinsäure | |
| DE2708112C3 (de) | Verfahren zur mikrobiologischen Erzeugung von Protein | |
| DE2704070A1 (de) | Verfahren zur herstellung von vitamin b tief 12 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: TAUCHNER, P., DIPL.-CHEM. DR.RER.NAT. HEUNEMANN, D., DIPL.-PHYS. DR.RER.NAT. RAUH, P., DIPL.-CHEM. DR.RER.NAT. HERMANN, G., DIPL.-PHYS. DR.RER.NAT. SCHMIDT, J., DIPL.-ING. JAENICHEN, H., DIPL.-BIOL. DR.RER.NAT., PAT.-ANWAELTE TREMMEL, H., RECHTSANW., 8000 MUENCHEN |