DK1636246T3 - Preparation of 2-desoxynucleosider and 2-desoxynucleosidforstadier from 2-dehydro-3-deoxy-D-gluconate - Google Patents

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Publication number

DK1636246T3

DK1636246T3 DK04740261.5T DK04740261T DK1636246T3 DK 1636246 T3 DK1636246 T3 DK 1636246T3 DK 04740261 T DK04740261 T DK 04740261T DK 1636246 T3 DK1636246 T3 DK 1636246T3

Authority

DK

Denmark

Prior art keywords

ala

leu

gly

val

glu

Prior art date

2003-06-24

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• WPAMZTWLKIDIOP-WVZVXSGGSA-N 2-dehydro-3-deoxy-D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)CC(=O)C(O)=O WPAMZTWLKIDIOP-WVZVXSGGSA-N 0.000 title claims description 112
• 238000002360 preparation method Methods 0.000 title claims description 26
• 238000000034 method Methods 0.000 claims description 96
• ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 claims description 71
• 108010011939 Pyruvate Decarboxylase Proteins 0.000 claims description 64
• 150000001875 compounds Chemical class 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 48
• UFYKDFXCZBTLOO-TXICZTDVSA-N 2-amino-2-deoxy-D-gluconic acid Chemical compound [O-]C(=O)[C@H]([NH3+])[C@@H](O)[C@H](O)[C@H](O)CO UFYKDFXCZBTLOO-TXICZTDVSA-N 0.000 claims description 47
• 230000000694 effects Effects 0.000 claims description 36
• 108010071778 Benzoylformate decarboxylase Proteins 0.000 claims description 31
• 230000008569 process Effects 0.000 claims description 31
• 102000004190 Enzymes Human genes 0.000 claims description 30
• 108090000790 Enzymes Proteins 0.000 claims description 30
• 238000006114 decarboxylation reaction Methods 0.000 claims description 30
• 101710125669 D-galactonate dehydratase family member RspA Proteins 0.000 claims description 29
• 101710095404 D-gluconate dehydratase Proteins 0.000 claims description 29
• 238000006243 chemical reaction Methods 0.000 claims description 27
• 108090000489 Carboxy-Lyases Proteins 0.000 claims description 26
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• 239000002773 nucleotide Substances 0.000 claims description 25
• 125000003729 nucleotide group Chemical group 0.000 claims description 25
• RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims description 24
• 239000002243 precursor Substances 0.000 claims description 22
• 108091028043 Nucleic acid sequence Proteins 0.000 claims description 20
• 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 20
• 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims description 20
• 150000004715 keto acids Chemical class 0.000 claims description 17
• 108030003555 Phosphonopyruvate decarboxylases Proteins 0.000 claims description 16
• -1 acetate ester Chemical class 0.000 claims description 16
• 241000588902 Zymomonas mobilis Species 0.000 claims description 15
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• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 14
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
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• 229920001184 polypeptide Polymers 0.000 claims description 13
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• 108020004707 nucleic acids Proteins 0.000 claims description 10
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• 102000040430 polynucleotide Human genes 0.000 claims description 10
• YXVCLPJQTZXJLH-UHFFFAOYSA-N thiamine(1+) diphosphate chloride Chemical compound [Cl-].CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N YXVCLPJQTZXJLH-UHFFFAOYSA-N 0.000 claims description 10
• 108030003516 Sulfopyruvate decarboxylases Proteins 0.000 claims description 9
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• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
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• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
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• 125000006239 protecting group Chemical group 0.000 claims description 3
• HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 claims description 2
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
• 108010021680 2-oxoglutarate decarboxylase Proteins 0.000 claims description 2
• KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims description 2
• ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 2
• 241000589220 Acetobacter Species 0.000 claims description 2
• RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 2
• 239000007868 Raney catalyst Substances 0.000 claims description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
• 241001464778 Zymobacter Species 0.000 claims description 2
• 241000588901 Zymomonas Species 0.000 claims description 2
• XXFXTBNFFMQVKJ-UHFFFAOYSA-N [diphenyl(trityloxy)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XXFXTBNFFMQVKJ-UHFFFAOYSA-N 0.000 claims description 2
• MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 2
• 125000004122 cyclic group Chemical group 0.000 claims description 2
• MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 2
• 229950006191 gluconic acid Drugs 0.000 claims description 2
• 235000012208 gluconic acid Nutrition 0.000 claims description 2
• 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 2
• 229910052757 nitrogen Inorganic materials 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 2
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• 239000004224 potassium gluconate Substances 0.000 claims description 2
• 235000013926 potassium gluconate Nutrition 0.000 claims description 2
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• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 2
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• MSXHSNHNTORCAW-GGLLEASOSA-M sodium;(2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate Chemical compound [Na+].O[C@H]1O[C@H](C([O-])=O)[C@@H](O)[C@H](O)[C@H]1O MSXHSNHNTORCAW-GGLLEASOSA-M 0.000 claims description 2
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• FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 claims description 2
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