IL94694A - Enantiomeric enrichment and straoselective synthesis of chiral amines - Google Patents

Enantiomeric enrichment and straoselective synthesis of chiral amines

Info

Publication number: IL94694A
Authority: IL; Israel
Prior art keywords: amino; chiral; process according; omega; ketone
Prior art date: 1989-06-22

Application number

IL9469490A

Other languages

English (en)

Hebrew (he)

Other versions

IL94694A0 (en

Inventor

David I Stirling

Andrew L Zeitlin

George W Matcham

Original Assignee

Celgene Corp

Priority date (The priority date 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 date listed.)

1989-06-22

Filing date

1990-06-11

Publication date

1996-10-16

1990-06-11 Application filed by Celgene Corp filed Critical Celgene Corp

1991-04-15 Publication of IL94694A0 publication Critical patent/IL94694A0/xx

1996-10-16 Publication of IL94694A publication Critical patent/IL94694A/en

Links

150000001412 amines Chemical class 0.000 title claims abstract description 89
230000015572 biosynthetic process Effects 0.000 title claims description 15
230000000707 stereoselective effect Effects 0.000 title claims description 14
238000003786 synthesis reaction Methods 0.000 title claims description 14
238000000034 method Methods 0.000 claims abstract description 69
108090000340 Transaminases Proteins 0.000 claims abstract description 58
150000002576 ketones Chemical class 0.000 claims abstract description 32
102000003929 Transaminases Human genes 0.000 claims abstract description 19
125000003277 amino group Chemical group 0.000 claims abstract description 13
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 44
239000000203 mixture Substances 0.000 claims description 22
238000002360 preparation method Methods 0.000 claims description 17
244000005700 microbiome Species 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
230000002401 inhibitory effect Effects 0.000 claims description 7
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 6
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical group CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 4
239000012736 aqueous medium Substances 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical group OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 4
KHPXUQMNIQBQEV-UHFFFAOYSA-N oxaloacetic acid Chemical compound OC(=O)CC(=O)C(O)=O KHPXUQMNIQBQEV-UHFFFAOYSA-N 0.000 claims description 4
239000004471 Glycine Substances 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000003884 phenylalkyl group Chemical group 0.000 claims description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
150000001299 aldehydes Chemical class 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
229940107700 pyruvic acid Drugs 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
235000004279 alanine Nutrition 0.000 claims 1
235000003704 aspartic acid Nutrition 0.000 claims 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 claims 1
239000012429 reaction media Substances 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 abstract description 14
230000007717 exclusion Effects 0.000 abstract 1
229940024606 amino acid Drugs 0.000 description 49
102000014898 transaminase activity proteins Human genes 0.000 description 39
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 32
102000004190 Enzymes Human genes 0.000 description 23
108090000790 Enzymes Proteins 0.000 description 23
230000000694 effects Effects 0.000 description 22
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 22
239000000370 acceptor Substances 0.000 description 21
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
-1 A-butyl Chemical group 0.000 description 11
241000193830 Bacillus <bacterium> Species 0.000 description 11
235000007682 pyridoxal 5'-phosphate Nutrition 0.000 description 11
239000011589 pyridoxal 5'-phosphate Substances 0.000 description 11
229960001327 pyridoxal phosphate Drugs 0.000 description 11
WECUIGDEWBNQJJ-SECBINFHSA-N (2r)-4-phenylbutan-2-amine Chemical compound C[C@@H](N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-SECBINFHSA-N 0.000 description 10
230000002255 enzymatic effect Effects 0.000 description 10
239000000047 product Substances 0.000 description 10
DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000284 extract Substances 0.000 description 9
239000008363 phosphate buffer Substances 0.000 description 9
239000000243 solution Substances 0.000 description 9
RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 8
235000001014 amino acid Nutrition 0.000 description 8
150000001413 amino acids Chemical class 0.000 description 8
238000003556 assay Methods 0.000 description 8
239000002609 medium Substances 0.000 description 8
229940076788 pyruvate Drugs 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 7
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 6
229960003767 alanine Drugs 0.000 description 6
229940067621 aminobutyrate Drugs 0.000 description 6
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 6
238000006911 enzymatic reaction Methods 0.000 description 6
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 6
238000000605 extraction Methods 0.000 description 5
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 5
229940054269 sodium pyruvate Drugs 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
238000005119 centrifugation Methods 0.000 description 4
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
239000011159 matrix material Substances 0.000 description 4
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
239000001632 sodium acetate Substances 0.000 description 4
235000017281 sodium acetate Nutrition 0.000 description 4
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229940000635 beta-alanine Drugs 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
230000000937 inactivator Effects 0.000 description 3
238000011534 incubation Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
150000003141 primary amines Chemical class 0.000 description 3
238000000926 separation method Methods 0.000 description 3
241000894007 species Species 0.000 description 3
229960003732 tyramine Drugs 0.000 description 3
SOZMSEPDYJGBEK-ZCFIWIBFSA-N (1r)-1-(4-bromophenyl)ethanamine Chemical compound C[C@@H](N)C1=CC=C(Br)C=C1 SOZMSEPDYJGBEK-ZCFIWIBFSA-N 0.000 description 2
BHRZNVHARXXAHW-SCSAIBSYSA-N (2r)-butan-2-amine Chemical compound CC[C@@H](C)N BHRZNVHARXXAHW-SCSAIBSYSA-N 0.000 description 2
SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 description 2
WFWKNGZODAOLEO-UHFFFAOYSA-N 1-(4-Methoxyphenyl)-2-propanone Chemical compound COC1=CC=C(CC(C)=O)C=C1 WFWKNGZODAOLEO-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
108030000921 4-aminobutyrate-2-oxoglutarate transaminases Proteins 0.000 description 2
WECUIGDEWBNQJJ-UHFFFAOYSA-N 4-phenylbutan-2-amine Chemical compound CC(N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-UHFFFAOYSA-N 0.000 description 2
SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
241000194107 Bacillus megaterium Species 0.000 description 2
108010010560 Beta-alanine-pyruvate transaminase Proteins 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
108010093096 Immobilized Enzymes Proteins 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000589516 Pseudomonas Species 0.000 description 2
241000589776 Pseudomonas putida Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
241000187747 Streptomyces Species 0.000 description 2
229960002684 aminocaproic acid Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
238000012258 culturing Methods 0.000 description 2
229960003692 gamma aminobutyric acid Drugs 0.000 description 2
239000008103 glucose Substances 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229960003104 ornithine Drugs 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
239000001294 propane Substances 0.000 description 2
235000018102 proteins Nutrition 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
NHZMQXZHNVQTQA-UHFFFAOYSA-N pyridoxamine Chemical compound CC1=NC=C(CO)C(CN)=C1O NHZMQXZHNVQTQA-UHFFFAOYSA-N 0.000 description 2
238000009877 rendering Methods 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
239000001488 sodium phosphate Substances 0.000 description 2
229910000162 sodium phosphate Inorganic materials 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
229960003080 taurine Drugs 0.000 description 2
238000005891 transamination reaction Methods 0.000 description 2
230000009466 transformation Effects 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
KFNRJXCQEJIBER-UHFFFAOYSA-N (+-)-Gabaculin Natural products NC1CC(C(O)=O)=CC=C1 KFNRJXCQEJIBER-UHFFFAOYSA-N 0.000 description 1
JMHAKVPFYWWNOW-SECBINFHSA-N (2r)-4-(4-methoxyphenyl)butan-2-amine Chemical compound COC1=CC=C(CC[C@@H](C)N)C=C1 JMHAKVPFYWWNOW-SECBINFHSA-N 0.000 description 1
FVWVJTJAALVOQO-SECBINFHSA-N (2r)-5-pyridin-3-ylpentan-2-amine Chemical compound C[C@@H](N)CCCC1=CC=CN=C1 FVWVJTJAALVOQO-SECBINFHSA-N 0.000 description 1
JCBPETKZIGVZRE-BYPYZUCNSA-N (2s)-2-aminobutan-1-ol Chemical compound CC[C@H](N)CO JCBPETKZIGVZRE-BYPYZUCNSA-N 0.000 description 1
KWTSXDURSIMDCE-MRVPVSSYSA-N (R)-amphetamine Chemical compound C[C@@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-MRVPVSSYSA-N 0.000 description 1
KFNRJXCQEJIBER-ZCFIWIBFSA-N (S)-gabaculine Chemical compound N[C@H]1CC(C(O)=O)=CC=C1 KFNRJXCQEJIBER-ZCFIWIBFSA-N 0.000 description 1
WYECURVXVYPVAT-UHFFFAOYSA-N 1-(4-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C=C1 WYECURVXVYPVAT-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
MLBHFBKZUPLWBD-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]-2-propanamine Chemical compound CC(N)CC1=CC=CC(C(F)(F)F)=C1 MLBHFBKZUPLWBD-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
AQFLVLHRZFLDDV-UHFFFAOYSA-N 1-phenylpropan-1-amine Chemical compound CCC(N)C1=CC=CC=C1 AQFLVLHRZFLDDV-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
KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical compound OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 description 1
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Aminopropanesulfonate Chemical compound NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 description 1
QCHPKSFMDHPSNR-UHFFFAOYSA-N 3-aminoisobutyric acid Chemical compound NCC(C)C(O)=O QCHPKSFMDHPSNR-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
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
ULGJWNIHLSLQPZ-UHFFFAOYSA-N 7-[(6,8-dichloro-1,2,3,4-tetrahydroacridin-9-yl)amino]-n-[2-(1h-indol-3-yl)ethyl]heptanamide Chemical compound C1CCCC2=NC3=CC(Cl)=CC(Cl)=C3C(NCCCCCCC(=O)NCCC=3C4=CC=CC=C4NC=3)=C21 ULGJWNIHLSLQPZ-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
UQXNEWQGGVUVQA-UHFFFAOYSA-N 8-aminooctanoic acid Chemical compound NCCCCCCCC(O)=O UQXNEWQGGVUVQA-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
229920000936 Agarose Polymers 0.000 description 1
108700023418 Amidases Proteins 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000228212 Aspergillus Species 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical class C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
241000051622 Bacillus meqaterium Species 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
241000222120 Candida <Saccharomycetales> Species 0.000 description 1
101150015280 Cel gene Proteins 0.000 description 1
240000001817 Cereus hexagonus Species 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
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Classifications

- 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
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/10—Transferases (2.)
- C12N9/1096—Transferases (2.) transferring nitrogenous groups (2.6)
- 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
- 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
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
- C12P7/26—Ketones

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Biotechnology (AREA)
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Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Analytical Chemistry (AREA)
Biomedical Technology (AREA)
Molecular Biology (AREA)
Medicinal Chemistry (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL9469490A 1989-06-22 1990-06-11 Enantiomeric enrichment and straoselective synthesis of chiral amines IL94694A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/369,723 US4950606A (en)	1989-06-22	1989-06-22	Enantiomeric enrichment and stereoselective synthesis of chiral amines

Publications (2)

Publication Number	Publication Date
IL94694A0 IL94694A0 (en)	1991-04-15
IL94694A true IL94694A (en)	1996-10-16

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ID=23456647

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Application Number	Title	Priority Date	Filing Date
IL9469490A IL94694A (en)	1989-06-22	1990-06-11	Enantiomeric enrichment and straoselective synthesis of chiral amines

Country Status (18)

Country	Link
US (1)	US4950606A (ja)
EP (1)	EP0404146B1 (ja)
JP (1)	JP2846074B2 (ja)
KR (1)	KR0147827B1 (ja)
AT (1)	ATE135744T1 (ja)
AU (1)	AU628183B2 (ja)
CA (1)	CA2018773C (ja)
DE (1)	DE69025988T2 (ja)
DK (1)	DK0404146T3 (ja)
ES (1)	ES2084618T3 (ja)
GR (1)	GR3019682T3 (ja)
HK (1)	HK1008052A1 (ja)
HU (1)	HU210967B (ja)
IE (1)	IE72956B1 (ja)
IL (1)	IL94694A (ja)
NZ (1)	NZ234154A (ja)
RU (2)	RU2087536C1 (ja)
ZA (1)	ZA904571B (ja)

Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3842025A1 (de) *	1988-12-14	1990-07-05	Hoechst Ag	Verfahren zur herstellung von l-phosphinothricin
US5169780A (en) *	1989-06-22	1992-12-08	Celgene Corporation	Enantiomeric enrichment and stereoselective synthesis of chiral amines
US5141904A (en) *	1991-02-15	1992-08-25	Phillips Petroleum Company	Reactivation of spent cracking catalysts
CA2077400A1 (en) *	1991-10-08	1993-04-09	Mikhail Leyderman	Mandrel and a method of making a rigid tubular article
US5439873A (en) *	1994-02-23	1995-08-08	Plant Growth Development Corporation	Method for stimulating plant growth using GABA
US6534446B1 (en)	1994-02-23	2003-03-18	Emerald Bioagriculture Corporation	Method to mitigate plant stress
US5840656A (en) *	1994-02-23	1998-11-24	Auxein Corporation	Method for increasing fertilizer efficiency
WO1997015682A1 (en)	1995-10-23	1997-05-01	Kaneka Corporation	Process for producing optically active amino compounds
JPH10165194A (ja) *	1996-12-12	1998-06-23	Sumitomo Chem Co Ltd	光学純度の向上方法
EP0987332B1 (en) *	1997-04-23	2009-08-19	Kaneka Corporation	DNA encoding a polypeptide having stereoselective transaminase activity, and transformants comprising said DNA
PL342882A1 (en) *	1998-03-11	2001-07-16	Celgro	Improvements in the enzymatic synthesis of chiral amines
ATE412047T1 (de) *	1998-10-30	2008-11-15	Kaneka Corp	(s)-alpha-phenethylamin: pyruvattransaminase
US6432688B1 (en)	1999-01-18	2002-08-13	Daicel Chemical Industries, Ltd.	Amino alcohol dehydrogenase converts keto alcohol to amino alcohol and amino alcohol to keto alcohol
DE60013939T2 (de)	1999-03-19	2005-10-06	Sumitomo Chemical Co. Ltd.	Stereoselektive Transaminase, deren kodierende Gen und deren Verwendungen
JP4496593B2 (ja) *	1999-03-19	2010-07-07	住友化学株式会社	蛋白質、その遺伝子及びその利用
US6252114B1 (en) *	2000-03-24	2001-06-26	Council Of Scientific And Industrial Research	Process for preparing novel biologically active synthetic molecule 4-(p-methoxyphenyl)-2-amino-butane
RU2177114C2 (ru) *	2000-04-03	2001-12-20	ООО "Самаратрансгаз"	Устройство для крепления жаровой трубы в корпусе камеры сгорания
US7067291B2 (en) *	2002-12-20	2006-06-27	Pfizer Inc.	Biocatalytic preparation of enantiomerically enriched aminopentanenitrile
US20050009151A1 (en) *	2003-07-10	2005-01-13	Pharmacia Corporation	Methods for the stereospecific and enantiomeric enrichment of beta-amino acids
US7172885B2 (en) *	2004-12-10	2007-02-06	Cambrex North Brunswick, Inc.	Thermostable omega-transaminases
US8133705B2 (en)	2005-05-23	2012-03-13	Kaneka Corporation	Aminotransferase, gene encoding the same, and method of using them
EP1818411A1 (en) *	2006-02-13	2007-08-15	Lonza AG	Process for the preparation of optically active chiral amines
EP1897956A1 (en) *	2006-09-06	2008-03-12	Lonza AG	Process for preparation of optically active amines by optical resolution of racemic amines employing a bacterial omega-transaminase
US8826958B2 (en)	2007-02-27	2014-09-09	Mani, Inc.	Crimping device for attaching a medical suture thread to a medical suture needle
DE102007042600A1 (de)	2007-09-07	2009-03-12	Evonik Degussa Gmbh	Verfahren zur Herstellung von enantiomerenangereichten Aminen
CA2724648A1 (en) *	2008-05-22	2009-11-26	Merck Sharp & Dohme Corp.	Process for the preparation of an orexin receptor antagonist
ES2840000T3 (es)	2009-01-08	2021-07-06	Codexis Inc	Polipéptidos de transaminasa
DE102009000592A1 (de)	2009-02-04	2010-08-05	Evonik Degussa Gmbh	Verfahren zur Herstellung von Aminogruppen tragenden, multizyklischen Ringsystemen
SG173815A1 (en)	2009-02-26	2011-09-29	Codexis Inc	Transaminase biocatalysts
ES2644992T3 (es)	2009-06-22	2017-12-01	Codexis, Inc.	Reacciones de transaminasa
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
JP2015533501A (ja) *	2012-10-18	2015-11-26	サンド・アクチエンゲゼルシヤフト	インドリン誘導体の調製方法
CA2895752C (en)	2012-12-21	2021-09-21	Codexis, Inc.	Engineered biocatalysts and methods for synthesizing chiral amines
HUE042206T2 (hu)	2013-02-28	2019-06-28	Codexis Inc	Módosított transzamináz polipeptidek ipari biokatalízishez
CA3064574A1 (en)	2017-06-14	2018-12-20	Codexis, Inc.	Engineered transaminase polypeptides for industrial biocatalysis
KR20190109696A (ko)	2018-03-18	2019-09-26	양만주	재사용이 가능한 페트병 홀더
TWI851589B (zh)	2018-07-31	2024-08-11	德商拜耳廠股份有限公司	編碼改良之轉胺酶蛋白質之核酸
WO2020150125A1 (en)	2019-01-15	2020-07-23	Codexis, Inc.	Engineered transaminase polypeptides
CN115427557A (zh)	2020-04-10	2022-12-02	科德克希思公司	工程化转氨酶多肽
AU2022347282A1 (en) *	2021-09-15	2024-05-02	Budapesti Műszaki és Gazdaságtudományi Egyetem	PROCESS TO PRODUCE (1r,4r)-4-SUBSTITUTED CYCLOHEXANE-1-AMINES
CN119060058A (zh) *	2024-08-21	2024-12-03	武汉九州钰民医药科技有限公司	一种甲苯磺酸利特昔替尼的合成方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3871958A (en) *	1972-03-04	1975-03-18	Ajinomoto Kk	Biological method of producing serine and serinol derivatives
US3944608A (en) *	1976-02-20	1976-03-16	American Cyanamid Company	Synthesis of N-[1-(chloromethyl)propyl]acetamide
WO1980002157A1 (en) *	1979-04-06	1980-10-16	Forenede Bryggerier As	A process for enzymatic production of peptides
JPS55138389A (en) *	1979-04-14	1980-10-29	Denki Kagaku Kogyo Kk	Preparation of amino alcohols
JPS58198296A (ja) *	1982-05-12	1983-11-18	Chisso Corp	ｄ−２−アミノブタノ−ルの製造法
JPS5939294A (ja) *	1982-08-27	1984-03-03	Hamari Yakuhin Kogyo Kk	光学活性２−アミノ−１−ブタノ−ルの製造法
EP0135846B1 (en) *	1983-09-01	1990-08-16	Genetics Institute, Inc.	Production of l-amino acids by transamination
IT1191638B (it) *	1985-10-31	1988-03-23	Montedison Spa	Processo per la separazione enzimatica degli isomeri ottici del 2-amminobutanolo
US4620861A (en) *	1985-11-04	1986-11-04	Corning Glass Works	Method for making index-profiled optical device
IT1188641B (it) *	1986-03-28	1988-01-20	Montedison Spa	Processo per la risoluzione enzimatica di 2-ammino-1-alcanoli racemi
JPS63237796A (ja) *	1987-03-25	1988-10-04	Kanegafuchi Chem Ind Co Ltd	光学活性１−メチル−３−フエニルプロピルアミンの製造法
JPS63273486A (ja) *	1987-04-30	1988-11-10	Tanabe Seiyaku Co Ltd	１−（４−メトキシフェニル）−２−アミノプロパンの製法
DE3818851A1 (de) *	1988-06-03	1989-12-14	Hoechst Ag	Neue transaminase, ihre herstellung und ihre verwendung

1989
- 1989-06-22 US US07/369,723 patent/US4950606A/en not_active Expired - Lifetime
1990
- 1990-06-11 IL IL9469490A patent/IL94694A/en active IP Right Grant
- 1990-06-12 CA CA002018773A patent/CA2018773C/en not_active Expired - Lifetime
- 1990-06-13 ZA ZA904571A patent/ZA904571B/xx unknown
- 1990-06-14 IE IE215990A patent/IE72956B1/en not_active IP Right Cessation
- 1990-06-19 AU AU57541/90A patent/AU628183B2/en not_active Expired
- 1990-06-20 NZ NZ234154A patent/NZ234154A/xx unknown
- 1990-06-21 ES ES90111754T patent/ES2084618T3/es not_active Expired - Lifetime
- 1990-06-21 RU SU904830607A patent/RU2087536C1/ru active
- 1990-06-21 DK DK90111754.9T patent/DK0404146T3/da active
- 1990-06-21 DE DE69025988T patent/DE69025988T2/de not_active Expired - Lifetime
- 1990-06-21 HU HU903945A patent/HU210967B/hu unknown
- 1990-06-21 EP EP90111754A patent/EP0404146B1/en not_active Expired - Lifetime
- 1990-06-21 AT AT90111754T patent/ATE135744T1/de not_active IP Right Cessation
- 1990-06-21 RU RU93004462A patent/RU2116347C1/ru active
- 1990-06-22 KR KR1019900009317A patent/KR0147827B1/ko not_active Expired - Lifetime
- 1990-06-22 JP JP2165480A patent/JP2846074B2/ja not_active Expired - Lifetime
1996
- 1996-04-19 GR GR960401061T patent/GR3019682T3/el unknown
1998
- 1998-06-27 HK HK98107175A patent/HK1008052A1/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
HU210967B (en)	1995-09-28
JPH03103192A (ja)	1991-04-30
GR3019682T3 (en)	1996-07-31
EP0404146A3 (en)	1992-03-11
CA2018773C (en)	2000-03-21
KR910000616A (ko)	1991-01-29
DE69025988T2 (de)	1996-08-14
EP0404146B1 (en)	1996-03-20
CA2018773A1 (en)	1990-12-22
IL94694A0 (en)	1991-04-15
DK0404146T3 (da)	1996-06-17
NZ234154A (en)	1991-08-27
JP2846074B2 (ja)	1999-01-13
AU5754190A (en)	1991-01-03
RU2116347C1 (ru)	1998-07-27
US4950606A (en)	1990-08-21
AU628183B2 (en)	1992-09-10
DE69025988D1 (de)	1996-04-25
IE72956B1 (en)	1997-05-07
RU2087536C1 (ru)	1997-08-20
IE902159L (en)	1990-12-22
HK1008052A1 (en)	1999-04-30
IE902159A1 (en)	1991-01-02
ZA904571B (en)	1991-03-27
ES2084618T3 (es)	1996-05-16
HU903945D0 (en)	1990-11-28
ATE135744T1 (de)	1996-04-15
KR0147827B1 (ko)	1998-08-01
EP0404146A2 (en)	1990-12-27
HUT54423A (en)	1991-02-28

Legal Events

Date	Code	Title
1997-03-18	FF	Patent granted
1997-06-10	KB	Patent renewed
2004-07-25	KB	Patent renewed
2008-11-03	KB	Patent renewed

Publication	Publication Date	Title
EP0404146B1 (en)	1996-03-20	Enantiomeric enrichment and stereoselective synthesis of chiral amines
US5300437A (en)	1994-04-05	Enantiomeric enrichment and stereoselective synthesis of chiral amines
HK1008052B (en)	1999-04-30	Enantiomeric enrichment and stereoselective synthesis of chiral amines
US5169780A (en)	1992-12-08	Enantiomeric enrichment and stereoselective synthesis of chiral amines
CA2659300C (en)	2014-02-18	Process for preparation of optically active n-protected 3-aminopyrrolidine or optically active n-protected 3-aminopiperidine and the corresponding ketones by optical resolution ofthe racemic amine mixtures employing a bacterial omega-transaminase
JP3717535B2 (ja)	2005-11-16	新規微生物およびＬ−α−アミノ酸の製法
Kamphuis et al.	2005	New developments in the chemo-enzymatic production of amino acids
CZ20013901A3 (cs)	2002-02-13	Způsob výroby L-fosfinothricinu enzymatickou transaminací a aspartátem
EP0330695B1 (en)	1992-11-11	Process for preparation of organic chemicals
EP0206904B1 (fr)	1992-03-18	Procédé de production enzymatique de L-alpha-aminoacides à partir d'chi cétoacides
EP1075534B1 (en)	2005-05-11	Improvements in the enzymatic synthesis of chiral amines
US5219731A (en)	1993-06-15	Method for preparing optically-active amino acid derivatives
US6133018A (en)	2000-10-17	Enzymatic synthesis of chiral amines using -2-amino propane as amine donor
CZ283867B6 (cs)	1998-06-17	Způsob enantiomerického obohacování a stereoselektivní syntézy chirálních aminů
SK280218B6 (sk)	1999-10-08	Spôsob enantiomérneho obohacovania a stereoselektí
Stirling	1993	ENANTIOMERICALLY PURE COMPOUNDS
JPS62205781A (ja)	1987-09-10	シユ−ドモナス属菌株の培養方法
AU2024254114A1 (en)	2025-09-11	A process for preparation of l-glufosinate or salts thereof
EP0352846A1 (en)	1990-01-31	Process for the preparation of biocatalysts with previously absent stereoselective enzyme activity
HK1035000B (en)	2005-12-23	Improvements in the enzymatic synthesis of chiral amines
JPWO1997015682A1 (ja)	1998-12-22	光学活性なアミノ化合物の製造方法