SE519168C2 - Förfarande för Isomerisation av organogermaniumföreningar - Google Patents
Förfarande för Isomerisation av organogermaniumföreningarInfo
- Publication number
- SE519168C2 SE519168C2 SE9402735A SE9402735A SE519168C2 SE 519168 C2 SE519168 C2 SE 519168C2 SE 9402735 A SE9402735 A SE 9402735A SE 9402735 A SE9402735 A SE 9402735A SE 519168 C2 SE519168 C2 SE 519168C2
- Authority
- SE
- Sweden
- Prior art keywords
- compound
- isomerization
- group
- process according
- glucose
- Prior art date
Links
- 238000006317 isomerization reaction Methods 0.000 title claims abstract description 93
- 238000000034 method Methods 0.000 title claims abstract description 40
- 125000000082 organogermanium group Chemical group 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- -1 organogermanium compound Chemical class 0.000 claims abstract description 62
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical group OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 claims abstract description 18
- 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 35
- 239000008103 glucose Substances 0.000 claims description 35
- 239000000243 solution Substances 0.000 claims description 32
- 229930091371 Fructose Natural products 0.000 claims description 27
- 239000005715 Fructose Substances 0.000 claims description 27
- 108090000790 Enzymes Proteins 0.000 claims description 26
- 102000004190 Enzymes Human genes 0.000 claims description 26
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 14
- 150000002584 ketoses Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229960000511 lactulose Drugs 0.000 claims description 9
- 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 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- GUBGYTABKSRVRQ-QKKXKWKRSA-N lactose group Chemical group OC1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](O2)CO)[C@H](O1)CO GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 8
- 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 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 208000007976 Ketosis Diseases 0.000 claims description 6
- 239000008101 lactose Substances 0.000 claims description 6
- 150000001323 aldoses Chemical group 0.000 claims description 4
- 238000005868 electrolysis reaction Methods 0.000 claims description 4
- 150000002016 disaccharides Chemical class 0.000 claims description 2
- 150000004676 glycans Chemical class 0.000 claims description 2
- 229920001282 polysaccharide Polymers 0.000 claims description 2
- 239000005017 polysaccharide Substances 0.000 claims description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims 1
- 229940126657 Compound 17 Drugs 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 1
- 150000002772 monosaccharides Chemical class 0.000 claims 1
- 229920001542 oligosaccharide Polymers 0.000 claims 1
- 150000002482 oligosaccharides Chemical class 0.000 claims 1
- 125000001553 ketosyl group Chemical group 0.000 abstract 2
- 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 31
- 229960001031 glucose Drugs 0.000 description 31
- 229940088598 enzyme Drugs 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 229920002472 Starch Polymers 0.000 description 9
- 235000021433 fructose syrup Nutrition 0.000 description 9
- 239000008107 starch Substances 0.000 description 9
- 235000019698 starch Nutrition 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 239000006188 syrup Substances 0.000 description 8
- 235000020357 syrup Nutrition 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229930006000 Sucrose Natural products 0.000 description 5
- 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 5
- 108700040099 Xylose isomerases Proteins 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000005720 sucrose Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 229910052732 germanium Inorganic materials 0.000 description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 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 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 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 2
- 108090000637 alpha-Amylases Proteins 0.000 description 2
- 239000012496 blank sample Substances 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229930182830 galactose Natural products 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 230000004140 ketosis Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 210000004088 microvessel Anatomy 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 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 1
- 241000187843 Actinoplanes missouriensis Species 0.000 description 1
- 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 1
- 241000186063 Arthrobacter Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000193749 Bacillus coagulans Species 0.000 description 1
- 241000186146 Brevibacterium Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000208152 Geranium Species 0.000 description 1
- 108010073178 Glucan 1,4-alpha-Glucosidase Proteins 0.000 description 1
- 102100022624 Glucoamylase Human genes 0.000 description 1
- 241000230491 Gulo Species 0.000 description 1
- 206010020575 Hyperammonaemia Diseases 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
- 108010093096 Immobilized Enzymes Proteins 0.000 description 1
- 240000001929 Lactobacillus brevis Species 0.000 description 1
- 235000013957 Lactobacillus brevis Nutrition 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 239000007993 MOPS buffer Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- NBGXQZRRLOGAJF-UHFFFAOYSA-N Maltulose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)(CO)OCC1O NBGXQZRRLOGAJF-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 241001467578 Microbacterium Species 0.000 description 1
- 102000016943 Muramidase Human genes 0.000 description 1
- 108010014251 Muramidase Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
- 206010029333 Neurosis Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical group [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 241000187759 Streptomyces albus Species 0.000 description 1
- 241001312733 Streptomyces griseofuscus Species 0.000 description 1
- 241000187411 Streptomyces phaeochromogenes Species 0.000 description 1
- 241000187417 Streptomyces rubiginosus Species 0.000 description 1
- 108010021119 Trichosanthin Proteins 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000010669 acid-base reaction Methods 0.000 description 1
- PYMYPHUHKUWMLA-VPENINKCSA-N aldehydo-D-xylose Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-VPENINKCSA-N 0.000 description 1
- 102000004139 alpha-Amylases Human genes 0.000 description 1
- 229940024171 alpha-amylase Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229940054340 bacillus coagulans Drugs 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001103 continuous-wave nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229940120503 dihydroxyacetone Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002231 fructose derivatives Chemical class 0.000 description 1
- 150000002303 glucose derivatives Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229960000274 lysozyme Drugs 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
- 235000010335 lysozyme Nutrition 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- JCQLYHFGKNRPGE-HFZVAGMNSA-N maltulose 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-HFZVAGMNSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 208000015238 neurotic disease Diseases 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003267 reducing disaccharides Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910001415 sodium ion Chemical group 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YITSIQZHKDXQEI-UHFFFAOYSA-N trichlorogermanium Chemical compound Cl[Ge](Cl)Cl YITSIQZHKDXQEI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/30—Germanium compounds
-
- 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
- C07H3/02—Monosaccharides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4360343A JPH06315391A (ja) | 1992-12-28 | 1992-12-28 | グルコースの異性化方法及び異性化促進剤 |
| JP5188877A JPH0717991A (ja) | 1993-06-30 | 1993-06-30 | アルドース構造を有する化合物をケトース構造を有する化合物へ異性化する方法、異性化或いはその促進剤 |
| PCT/JP1993/001896 WO1994014826A1 (en) | 1992-12-28 | 1993-12-27 | Process for isomerization of compound of aldose structure into compound of ketose structure, and isomerization agent or accelerator used therein |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE9402735L SE9402735L (sv) | 1994-08-16 |
| SE9402735D0 SE9402735D0 (sv) | 1994-08-16 |
| SE519168C2 true SE519168C2 (sv) | 2003-01-21 |
Family
ID=26505202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE9402735A SE519168C2 (sv) | 1992-12-28 | 1994-08-16 | Förfarande för Isomerisation av organogermaniumföreningar |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5679787A (de) |
| EP (1) | EP0628050B1 (de) |
| JP (1) | JP3524094B2 (de) |
| KR (1) | KR100344966B1 (de) |
| CN (1) | CN1036922C (de) |
| AU (1) | AU672865B2 (de) |
| CH (1) | CH685701A5 (de) |
| DE (2) | DE4396846B4 (de) |
| GB (1) | GB2279650B (de) |
| NL (1) | NL194441C (de) |
| NZ (1) | NZ250367A (de) |
| SE (1) | SE519168C2 (de) |
| WO (1) | WO1994014826A1 (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3668262B2 (ja) * | 1994-06-28 | 2005-07-06 | 株式会社浅井ゲルマニウム研究所 | 有機ゲルマニウム化合物の分離回収方法 |
| RU2476436C1 (ru) * | 2012-01-25 | 2013-02-27 | Общество С Ограниченной Ответственностью "Вдс Фарма" | Комплексные соединения германия с аминокислотами и карбоновыми кислотами |
| CN106032386B (zh) * | 2015-03-16 | 2019-03-15 | 中国科学院宁波材料技术与工程研究所 | 一种醛酮糖的催化转化方法 |
| WO2018148939A1 (zh) * | 2017-02-17 | 2018-08-23 | 中国科学院宁波材料技术与工程研究所 | 一种单糖差向异构化反应催化剂 |
| US20230109331A1 (en) * | 2020-01-06 | 2023-04-06 | Solugen, Inc. | Compositions, systems and methods for production of value-added chemicals |
| JP7416016B2 (ja) * | 2021-06-01 | 2024-01-17 | 株式会社豊田中央研究所 | 製造方法、使用方法及び反応システム |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1497888A (en) * | 1975-06-17 | 1978-01-12 | Ici Ltd | Aldose to ketose conversion |
| BE834794A (fr) * | 1975-10-23 | 1976-02-16 | Acide 3-trihydroxygermano-propionique | |
| GB1585174A (en) * | 1976-06-16 | 1981-02-25 | Ici Ltd | Separation of sugars from mixtures |
| JPS5632485A (en) * | 1979-08-24 | 1981-04-01 | Pola Chem Ind Inc | Preparation of organogermanium compound |
| CA1314210C (en) * | 1987-10-29 | 1993-03-09 | Norihiro Kakimoto | Agent for improving reduced functions of organs caused by inhibited blood circulation |
| JP3270969B2 (ja) * | 1990-04-13 | 2002-04-02 | 株式会社浅井ゲルマニウム研究所 | 光学活性な有機ゲルマニウム化合物の製造方法 |
| US5418298A (en) * | 1993-03-19 | 1995-05-23 | Regents Of The University Of Michigan | Neutral and mixed neutral/anionic polymetallooxanes |
-
1993
- 1993-12-06 NZ NZ250367A patent/NZ250367A/en not_active IP Right Cessation
- 1993-12-27 JP JP51501394A patent/JP3524094B2/ja not_active Expired - Fee Related
- 1993-12-27 DE DE4396846A patent/DE4396846B4/de not_active Expired - Fee Related
- 1993-12-27 CN CN93121222A patent/CN1036922C/zh not_active Expired - Fee Related
- 1993-12-27 AU AU57163/94A patent/AU672865B2/en not_active Ceased
- 1993-12-27 US US08/295,739 patent/US5679787A/en not_active Expired - Lifetime
- 1993-12-27 DE DE4396846T patent/DE4396846T1/de not_active Withdrawn
- 1993-12-27 CH CH2654/94A patent/CH685701A5/fr not_active IP Right Cessation
- 1993-12-27 WO PCT/JP1993/001896 patent/WO1994014826A1/en active IP Right Grant
- 1993-12-27 KR KR1019940702868A patent/KR100344966B1/ko not_active IP Right Cessation
- 1993-12-27 EP EP94903072A patent/EP0628050B1/de not_active Expired - Lifetime
- 1993-12-27 NL NL9320024A patent/NL194441C/nl not_active IP Right Cessation
- 1993-12-27 GB GB9416016A patent/GB2279650B/en not_active Expired - Fee Related
-
1994
- 1994-08-16 SE SE9402735A patent/SE519168C2/sv unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE9402735L (sv) | 1994-08-16 |
| EP0628050A1 (de) | 1994-12-14 |
| CH685701A5 (fr) | 1995-09-15 |
| WO1994014826A1 (en) | 1994-07-07 |
| NL194441C (nl) | 2002-04-04 |
| NL9320024A (nl) | 1995-03-01 |
| DE4396846B4 (de) | 2005-11-17 |
| SE9402735D0 (sv) | 1994-08-16 |
| GB9416016D0 (en) | 1994-09-28 |
| AU672865B2 (en) | 1996-10-17 |
| JP3524094B2 (ja) | 2004-04-26 |
| NL194441B (nl) | 2001-12-03 |
| KR100344966B1 (ko) | 2002-12-31 |
| JPH08502999A (ja) | 1996-04-02 |
| DE4396846T1 (de) | 1995-01-26 |
| CN1036922C (zh) | 1998-01-07 |
| AU5716394A (en) | 1994-07-19 |
| GB2279650A (en) | 1995-01-11 |
| NZ250367A (en) | 1995-10-26 |
| US5679787A (en) | 1997-10-21 |
| GB2279650B (en) | 1996-11-20 |
| EP0628050B1 (de) | 1998-04-08 |
| CN1094053A (zh) | 1994-10-26 |
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