UA64784C2 - Improvements in enzymatic synthesis of chiral amines - Google Patents
Improvements in enzymatic synthesis of chiral amines Download PDFInfo
- Publication number
- UA64784C2 UA64784C2 UA2000105759A UA2000105759A UA64784C2 UA 64784 C2 UA64784 C2 UA 64784C2 UA 2000105759 A UA2000105759 A UA 2000105759A UA 2000105759 A UA2000105759 A UA 2000105759A UA 64784 C2 UA64784 C2 UA 64784C2
- Authority
- UA
- Ukraine
- Prior art keywords
- aminopropane
- amino
- amino group
- transaminase
- acid
- Prior art date
Links
- 150000001412 amines Chemical class 0.000 title claims abstract description 35
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 18
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 18
- 230000006872 improvement Effects 0.000 title description 6
- 230000002255 enzymatic effect Effects 0.000 title description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims abstract description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 20
- 102000003929 Transaminases Human genes 0.000 claims abstract description 20
- 108090000340 Transaminases Proteins 0.000 claims abstract description 20
- CUZLJOLBIRPEFB-UHFFFAOYSA-N 1-methoxypropan-2-one Chemical compound COCC(C)=O CUZLJOLBIRPEFB-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000002576 ketones Chemical class 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims description 32
- 150000001413 amino acids Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 6
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 abstract description 8
- 230000000707 stereoselective effect Effects 0.000 abstract description 7
- 229940107700 pyruvic acid Drugs 0.000 abstract description 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 abstract description 2
- NXMXETCTWNXSFG-BYPYZUCNSA-N (2s)-1-methoxypropan-2-amine Chemical compound COC[C@H](C)N NXMXETCTWNXSFG-BYPYZUCNSA-N 0.000 abstract 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 abstract 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 abstract 1
- 229960003767 alanine Drugs 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 235000001014 amino acid Nutrition 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 12
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 description 12
- -1 b-aminohexanoic acid Chemical compound 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 description 7
- 239000011589 pyridoxal 5'-phosphate Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 229960001327 pyridoxal phosphate Drugs 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 4
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 4
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 150000004715 keto acids Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- GFAZHVHNLUBROE-UHFFFAOYSA-N 1-hydroxybutan-2-one Chemical compound CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 2
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 2
- ZIXLDMFVRPABBX-UHFFFAOYSA-N 2-methylcyclopentan-1-one Chemical compound CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 235000003704 aspartic acid Nutrition 0.000 description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 description 2
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
- NHZMQXZHNVQTQA-UHFFFAOYSA-N pyridoxamine Chemical compound CC1=NC=C(CO)C(CN)=C1O NHZMQXZHNVQTQA-UHFFFAOYSA-N 0.000 description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
- 229940054269 sodium pyruvate Drugs 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 229960003732 tyramine Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
- MLYCFWZIAJAIGW-UHFFFAOYSA-N 1-(2,5-dimethoxy-4-methylphenyl)butan-2-amine Chemical compound CCC(N)CC1=CC(OC)=C(C)C=C1OC MLYCFWZIAJAIGW-UHFFFAOYSA-N 0.000 description 1
- WKPWFAZJGVXPCH-UHFFFAOYSA-N 1-(4-bromophenyl)propan-1-amine Chemical compound CCC(N)C1=CC=C(Br)C=C1 WKPWFAZJGVXPCH-UHFFFAOYSA-N 0.000 description 1
- UOMOSYFPKGQIKI-UHFFFAOYSA-N 1-(4-bromophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(Br)C=C1 UOMOSYFPKGQIKI-UHFFFAOYSA-N 0.000 description 1
- WLNPAEJYFNAKKH-UHFFFAOYSA-N 1-(4-nitrophenyl)propan-1-amine Chemical compound CCC(N)C1=CC=C([N+]([O-])=O)C=C1 WLNPAEJYFNAKKH-UHFFFAOYSA-N 0.000 description 1
- JFNGTRVLHDCFOX-UHFFFAOYSA-N 1-(5-fluoro-2-methoxyphenyl)ethanamine Chemical compound COC1=CC=C(F)C=C1C(C)N JFNGTRVLHDCFOX-UHFFFAOYSA-N 0.000 description 1
- UBTPNKXHYILGJU-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=CC(C(F)(F)F)=C1 UBTPNKXHYILGJU-UHFFFAOYSA-N 0.000 description 1
- NXMXETCTWNXSFG-UHFFFAOYSA-N 1-methoxypropan-2-amine Chemical compound COCC(C)N NXMXETCTWNXSFG-UHFFFAOYSA-N 0.000 description 1
- TWASBYPJZBHZQJ-UHFFFAOYSA-N 1-methylcyclopentan-1-amine Chemical compound CC1(N)CCCC1 TWASBYPJZBHZQJ-UHFFFAOYSA-N 0.000 description 1
- WTKIGCDTNYVOMI-UHFFFAOYSA-N 1-methylperoxypropan-2-one Chemical compound COOCC(C)=O WTKIGCDTNYVOMI-UHFFFAOYSA-N 0.000 description 1
- KHSYYLCXQKCYQX-UHFFFAOYSA-N 1-naphthalen-2-ylethanamine Chemical compound C1=CC=CC2=CC(C(N)C)=CC=C21 KHSYYLCXQKCYQX-UHFFFAOYSA-N 0.000 description 1
- XHOXKVFLASIOJD-UHFFFAOYSA-N 1-phenylbutan-1-amine Chemical compound CCCC(N)C1=CC=CC=C1 XHOXKVFLASIOJD-UHFFFAOYSA-N 0.000 description 1
- GKDLTXYXODKDEA-UHFFFAOYSA-N 1-phenylbutan-2-one Chemical compound CCC(=O)CC1=CC=CC=C1 GKDLTXYXODKDEA-UHFFFAOYSA-N 0.000 description 1
- AQFLVLHRZFLDDV-UHFFFAOYSA-N 1-phenylpropan-1-amine Chemical compound CCC(N)C1=CC=CC=C1 AQFLVLHRZFLDDV-UHFFFAOYSA-N 0.000 description 1
- KWTSXDURSIMDCE-UHFFFAOYSA-N 1-phenylpropan-2-amine Chemical compound CC(N)CC1=CC=CC=C1 KWTSXDURSIMDCE-UHFFFAOYSA-N 0.000 description 1
- PCQKMDBZOIYAKY-UHFFFAOYSA-N 2,2-dimethylpentan-3-amine Chemical compound CCC(N)C(C)(C)C PCQKMDBZOIYAKY-UHFFFAOYSA-N 0.000 description 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 1
- FEUISMYEFPANSS-UHFFFAOYSA-N 2-methylcyclohexan-1-amine Chemical compound CC1CCCCC1N FEUISMYEFPANSS-UHFFFAOYSA-N 0.000 description 1
- LFSAPCRASZRSKS-UHFFFAOYSA-N 2-methylcyclohexan-1-one Chemical compound CC1CCCCC1=O LFSAPCRASZRSKS-UHFFFAOYSA-N 0.000 description 1
- 239000001903 2-oxo-3-phenylpropanoic acid Substances 0.000 description 1
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 description 1
- QHKABHOOEWYVLI-UHFFFAOYSA-N 3-methyl-2-oxobutanoic acid Chemical compound CC(C)C(=O)C(O)=O QHKABHOOEWYVLI-UHFFFAOYSA-N 0.000 description 1
- LGSSDLSVHUCRFI-UHFFFAOYSA-N 3-methylcyclopentan-1-amine Chemical compound CC1CCC(N)C1 LGSSDLSVHUCRFI-UHFFFAOYSA-N 0.000 description 1
- AOKRXIIIYJGNNU-UHFFFAOYSA-N 3-methylcyclopentan-1-one Chemical compound CC1CCC(=O)C1 AOKRXIIIYJGNNU-UHFFFAOYSA-N 0.000 description 1
- WNTVTQIJPAFZEL-UHFFFAOYSA-N 4-(3-aminobutyl)phenol Chemical compound CC(N)CCC1=CC=C(O)C=C1 WNTVTQIJPAFZEL-UHFFFAOYSA-N 0.000 description 1
- ABSTXSZPGHDTAF-UHFFFAOYSA-N 4-amino-pentanoic acid Chemical compound CC(N)CCC(O)=O ABSTXSZPGHDTAF-UHFFFAOYSA-N 0.000 description 1
- SXFSQZDSUWACKX-UHFFFAOYSA-N 4-methylthio-2-oxobutanoic acid Chemical compound CSCCC(=O)C(O)=O SXFSQZDSUWACKX-UHFFFAOYSA-N 0.000 description 1
- WECUIGDEWBNQJJ-UHFFFAOYSA-N 4-phenylbutan-2-amine Chemical compound CC(N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-UHFFFAOYSA-N 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005596 alkyl carboxamido group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- DEDGUGJNLNLJSR-UHFFFAOYSA-N alpha-hydroxycinnamic acid Natural products OC(=O)C(O)=CC1=CC=CC=C1 DEDGUGJNLNLJSR-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005533 aryl carboxamido group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- CLJMMQGDJNYDER-UHFFFAOYSA-N heptan-4-amine Chemical compound CCCC(N)CCC CLJMMQGDJNYDER-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 description 1
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- IOLQWLOHKZENDW-UHFFFAOYSA-N phenylisobutylamine Chemical compound CCC(N)CC1=CC=CC=C1 IOLQWLOHKZENDW-UHFFFAOYSA-N 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000008151 pyridoxamine Nutrition 0.000 description 1
- 239000011699 pyridoxamine Substances 0.000 description 1
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 238000004457 water analysis Methods 0.000 description 1
Classifications
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- 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/001—Amines; Imines
-
- 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
-
- 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/005—Amino acids other than alpha- or beta amino acids, e.g. gamma amino 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine
-
- 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/12—Methionine; Cysteine; Cystine
-
- 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
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7752098P | 1998-03-11 | 1998-03-11 | |
| PCT/US1999/005150 WO1999046398A1 (en) | 1998-03-11 | 1999-03-10 | Improvements in the enzymatic synthesis of chiral amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA64784C2 true UA64784C2 (en) | 2004-03-15 |
Family
ID=22138554
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2000105759A UA64784C2 (en) | 1998-03-11 | 1999-10-03 | Improvements in enzymatic synthesis of chiral amines |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP1075534B8 (cs) |
| JP (1) | JP2002505884A (cs) |
| KR (1) | KR20010034561A (cs) |
| CN (1) | CN1154746C (cs) |
| AT (1) | ATE295424T1 (cs) |
| AU (1) | AU753904B2 (cs) |
| BR (1) | BR9908797A (cs) |
| CA (1) | CA2322605A1 (cs) |
| CZ (1) | CZ295882B6 (cs) |
| DE (1) | DE69925267T2 (cs) |
| ES (1) | ES2243051T3 (cs) |
| FI (1) | FI20001805A (cs) |
| HK (1) | HK1035000A1 (cs) |
| HU (1) | HUP0101056A3 (cs) |
| MX (1) | MXPA00008573A (cs) |
| NO (1) | NO319671B1 (cs) |
| NZ (1) | NZ506405A (cs) |
| PL (1) | PL342882A1 (cs) |
| PT (1) | PT1075534E (cs) |
| RU (1) | RU2213142C2 (cs) |
| SK (1) | SK284352B6 (cs) |
| TR (1) | TR200002604T2 (cs) |
| UA (1) | UA64784C2 (cs) |
| WO (1) | WO1999046398A1 (cs) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1038953B1 (en) * | 1999-03-19 | 2004-09-22 | Sumitomo Chemical Company, Limited | Stereoselective transaminase, gene encoding said protein and use thereof |
| JP2001190298A (ja) * | 2000-01-13 | 2001-07-17 | Kanegafuchi Chem Ind Co Ltd | 光学活性ｎ−メチルアミノ酸の製造方法 |
| EP1818411A1 (en) * | 2006-02-13 | 2007-08-15 | Lonza AG | Process for the preparation of optically active chiral amines |
| DE102007042600A1 (de) | 2007-09-07 | 2009-03-12 | Evonik Degussa Gmbh | Verfahren zur Herstellung von enantiomerenangereichten Aminen |
| SG172891A1 (en) | 2009-01-08 | 2011-08-29 | Codexis Inc | Transaminase polypeptides |
| JP5707344B2 (ja) | 2009-02-26 | 2015-04-30 | コデクシス， インコーポレイテッド | トランスアミナーゼ生体触媒 |
| CN102597226B (zh) | 2009-06-22 | 2015-08-19 | 科德克希思公司 | 转氨酶反应 |
| ES2599644T3 (es) * | 2009-09-02 | 2017-02-02 | Lonza Ag | Un proceso para la identificación y preparación de una omega-transaminasa (R)-específica |
| US8852900B2 (en) | 2010-06-17 | 2014-10-07 | Codexis, Inc. | Biocatalysts and methods for the synthesis of (S)-3-(1-aminoethyl)-phenol |
| US8932836B2 (en) | 2010-08-16 | 2015-01-13 | Codexis, Inc. | Biocatalysts and methods for the synthesis of (1R,2R)-2-(3,4-dimethoxyphenethoxy)cyclohexanamine |
| JP6275642B2 (ja) * | 2011-08-16 | 2018-02-07 | エンバイオ・リミテツド | 光学活性キラルアミンの酵素的合成 |
| CN104630170A (zh) * | 2013-11-08 | 2015-05-20 | 中国科学院天津工业生物技术研究所 | 一种来源于里氏木霉的新(r)-转氨酶及其应用 |
| CN114134126B (zh) * | 2021-10-28 | 2023-12-05 | 浙江大学杭州国际科创中心 | 转氨酶及其突变体在制备(s)-1-甲氧基-2-丙胺中的应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5300437A (en) * | 1989-06-22 | 1994-04-05 | Celgene Corporation | Enantiomeric enrichment and stereoselective synthesis of chiral amines |
| DE69635082T2 (de) * | 1995-10-23 | 2006-06-01 | Kaneka Corp. | Verfahren zur herstellung optisch aktiver aminoverbindungen |
-
1999
- 1999-03-10 HU HU0101056A patent/HUP0101056A3/hu unknown
- 1999-03-10 DE DE69925267T patent/DE69925267T2/de not_active Expired - Fee Related
- 1999-03-10 BR BR9908797-9A patent/BR9908797A/pt not_active IP Right Cessation
- 1999-03-10 WO PCT/US1999/005150 patent/WO1999046398A1/en active IP Right Grant
- 1999-03-10 CA CA002322605A patent/CA2322605A1/en not_active Abandoned
- 1999-03-10 AT AT99911250T patent/ATE295424T1/de not_active IP Right Cessation
- 1999-03-10 AU AU29938/99A patent/AU753904B2/en not_active Ceased
- 1999-03-10 EP EP99911250A patent/EP1075534B8/en not_active Expired - Lifetime
- 1999-03-10 CN CNB99803651XA patent/CN1154746C/zh not_active Expired - Fee Related
- 1999-03-10 CZ CZ20003177A patent/CZ295882B6/cs not_active IP Right Cessation
- 1999-03-10 PL PL99342882A patent/PL342882A1/xx not_active IP Right Cessation
- 1999-03-10 RU RU2000125535/13A patent/RU2213142C2/ru active IP Right Revival
- 1999-03-10 NZ NZ506405A patent/NZ506405A/en not_active IP Right Cessation
- 1999-03-10 JP JP2000535765A patent/JP2002505884A/ja not_active Withdrawn
- 1999-03-10 PT PT99911250T patent/PT1075534E/pt unknown
- 1999-03-10 SK SK1338-2000A patent/SK284352B6/sk unknown
- 1999-03-10 MX MXPA00008573A patent/MXPA00008573A/es active IP Right Grant
- 1999-03-10 TR TR2000/02604T patent/TR200002604T2/xx unknown
- 1999-03-10 KR KR1020007009945A patent/KR20010034561A/ko active IP Right Grant
- 1999-03-10 ES ES99911250T patent/ES2243051T3/es not_active Expired - Lifetime
- 1999-10-03 UA UA2000105759A patent/UA64784C2/uk unknown
-
2000
- 2000-08-11 NO NO20004036A patent/NO319671B1/no unknown
- 2000-08-15 FI FI20001805A patent/FI20001805A/fi not_active IP Right Cessation
-
2001
- 2001-08-09 HK HK01105536A patent/HK1035000A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1075534A1 (en) | 2001-02-14 |
| RU2213142C2 (ru) | 2003-09-27 |
| HUP0101056A3 (en) | 2006-03-28 |
| BR9908797A (pt) | 2000-12-12 |
| CA2322605A1 (en) | 1999-09-16 |
| NO20004036L (no) | 2000-10-27 |
| WO1999046398A1 (en) | 1999-09-16 |
| EP1075534A4 (en) | 2003-07-09 |
| NO319671B1 (no) | 2005-09-05 |
| DE69925267T2 (de) | 2006-01-26 |
| JP2002505884A (ja) | 2002-02-26 |
| PL342882A1 (en) | 2001-07-16 |
| AU2993899A (en) | 1999-09-27 |
| ATE295424T1 (de) | 2005-05-15 |
| HK1035000A1 (en) | 2001-11-09 |
| ES2243051T3 (es) | 2005-11-16 |
| CZ20003177A3 (cs) | 2000-12-13 |
| AU753904B2 (en) | 2002-10-31 |
| CN1154746C (zh) | 2004-06-23 |
| HUP0101056A2 (hu) | 2001-07-30 |
| KR20010034561A (ko) | 2001-04-25 |
| CN1292828A (zh) | 2001-04-25 |
| FI20001805A (fi) | 2000-08-15 |
| EP1075534B1 (en) | 2005-05-11 |
| PT1075534E (pt) | 2005-09-30 |
| SK13382000A3 (sk) | 2001-05-10 |
| MXPA00008573A (es) | 2003-07-14 |
| CZ295882B6 (cs) | 2005-11-16 |
| SK284352B6 (sk) | 2005-02-04 |
| NO20004036D0 (no) | 2000-08-11 |
| DE69925267D1 (de) | 2005-06-16 |
| EP1075534B8 (en) | 2005-07-06 |
| NZ506405A (en) | 2003-08-29 |
| TR200002604T2 (tr) | 2000-11-21 |
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