NO326058B1 - Fremgangsmate for fremstilling av optisk aktive 1-amino-4-(hydroksymetyl)-cyklopenten-2-en-derivater - Google Patents
Fremgangsmate for fremstilling av optisk aktive 1-amino-4-(hydroksymetyl)-cyklopenten-2-en-derivater Download PDFInfo
- Publication number
- NO326058B1 NO326058B1 NO20013037A NO20013037A NO326058B1 NO 326058 B1 NO326058 B1 NO 326058B1 NO 20013037 A NO20013037 A NO 20013037A NO 20013037 A NO20013037 A NO 20013037A NO 326058 B1 NO326058 B1 NO 326058B1
- Authority
- NO
- Norway
- Prior art keywords
- amino
- hydroxymethyl
- cyclopent
- ene
- general formula
- Prior art date
Links
- -1 1-Amino-4- (Hydroxymethyl) Cyclopentene-2-ene Derivatives Chemical class 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 14
- UXKZFJDNFBNQHE-UHFFFAOYSA-N (4-aminocyclopent-2-en-1-yl)methanol Chemical class NC1CC(CO)C=C1 UXKZFJDNFBNQHE-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 9
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- 230000010933 acylation Effects 0.000 claims abstract description 7
- 238000005917 acylation reaction Methods 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 3
- 239000004367 Lipase Substances 0.000 claims description 36
- 102000004882 Lipase Human genes 0.000 claims description 32
- 108090001060 Lipase Proteins 0.000 claims description 32
- 235000019421 lipase Nutrition 0.000 claims description 32
- 102000004157 Hydrolases Human genes 0.000 claims description 9
- 108090000604 Hydrolases Proteins 0.000 claims description 9
- 108091005804 Peptidases Proteins 0.000 claims description 7
- 239000004365 Protease Substances 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 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 claims description 4
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 4
- 230000007073 chemical hydrolysis Effects 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 108090000371 Esterases Proteins 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 12
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 6
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 241000194110 Bacillus sp. (in: Bacteria) Species 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 241000589513 Burkholderia cepacia Species 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 108010020132 microbial serine proteinases Proteins 0.000 description 4
- JVSLVBYLHIRGJQ-SFYZADRCSA-N n-[(1r,4s)-4-(hydroxymethyl)cyclopent-2-en-1-yl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](CO)C=C1 JVSLVBYLHIRGJQ-SFYZADRCSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001661345 Moesziomyces antarcticus Species 0.000 description 3
- 241000498617 Mucor javanicus Species 0.000 description 3
- 102000035195 Peptidases Human genes 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UXKZFJDNFBNQHE-RITPCOANSA-N [(1s,4r)-4-aminocyclopent-2-en-1-yl]methanol Chemical compound N[C@@H]1C[C@H](CO)C=C1 UXKZFJDNFBNQHE-RITPCOANSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 240000006439 Aspergillus oryzae Species 0.000 description 2
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 108090000787 Subtilisin Proteins 0.000 description 2
- 108010056079 Subtilisins Proteins 0.000 description 2
- 102000005158 Subtilisins Human genes 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RCTIVAIYOJQQOV-MNOVXSKESA-N [(1s,4r)-4-acetamidocyclopent-2-en-1-yl]methyl butanoate Chemical compound CCCC(=O)OC[C@H]1C[C@@H](NC(C)=O)C=C1 RCTIVAIYOJQQOV-MNOVXSKESA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical class C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- XSSYCIGJYCVRRK-RQJHMYQMSA-N (-)-carbovir Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1C[C@H](CO)C=C1 XSSYCIGJYCVRRK-RQJHMYQMSA-N 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- WRMIVVLGWCQXNE-UHFFFAOYSA-N 2,2,2-trichloroethyl butanoate Chemical compound CCCC(=O)OCC(Cl)(Cl)Cl WRMIVVLGWCQXNE-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- SFTRWCBAYKQWCS-UHFFFAOYSA-N 2-butanoyloxyethyl butanoate Chemical compound CCCC(=O)OCCOC(=O)CCC SFTRWCBAYKQWCS-UHFFFAOYSA-N 0.000 description 1
- BNAPSUCFSUSJJW-UHFFFAOYSA-N 4-(trityloxymethyl)cyclopent-2-en-1-ol Chemical compound C1=CC(O)CC1COC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BNAPSUCFSUSJJW-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000194108 Bacillus licheniformis Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000222175 Diutina rugosa Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241001468249 Geobacillus thermocatenulatus Species 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
- 101710098556 Lipase A Proteins 0.000 description 1
- 101710098554 Lipase B Proteins 0.000 description 1
- 101710099648 Lysosomal acid lipase/cholesteryl ester hydrolase Proteins 0.000 description 1
- 102100026001 Lysosomal acid lipase/cholesteryl ester hydrolase Human genes 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 108010084311 Novozyme 435 Proteins 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- IGVPBCZDHMIOJH-UHFFFAOYSA-N Phenyl butyrate Chemical compound CCCC(=O)OC1=CC=CC=C1 IGVPBCZDHMIOJH-UHFFFAOYSA-N 0.000 description 1
- 241000589540 Pseudomonas fluorescens Species 0.000 description 1
- 241000589774 Pseudomonas sp. Species 0.000 description 1
- 101000968491 Pseudomonas sp. (strain 109) Triacylglycerol lipase Proteins 0.000 description 1
- 241000235403 Rhizomucor miehei Species 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- 241000235545 Rhizopus niveus Species 0.000 description 1
- 108010022999 Serine Proteases Proteins 0.000 description 1
- 102000012479 Serine Proteases Human genes 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 241000235015 Yarrowia lipolytica Species 0.000 description 1
- RCTIVAIYOJQQOV-WDEREUQCSA-N [(1r,4s)-4-acetamidocyclopent-2-en-1-yl]methyl butanoate Chemical compound CCCC(=O)OC[C@@H]1C[C@H](NC(C)=O)C=C1 RCTIVAIYOJQQOV-WDEREUQCSA-N 0.000 description 1
- UXKZFJDNFBNQHE-NTSWFWBYSA-N [(1r,4s)-4-aminocyclopent-2-en-1-yl]methanol Chemical compound N[C@H]1C[C@@H](CO)C=C1 UXKZFJDNFBNQHE-NTSWFWBYSA-N 0.000 description 1
- 241000179532 [Candida] cylindracea Species 0.000 description 1
- CXBNMPMLFONTPO-UHFFFAOYSA-N acetic benzoic anhydride Chemical compound CC(=O)OC(=O)C1=CC=CC=C1 CXBNMPMLFONTPO-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000011138 biotechnological process Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000006278 bromobenzyl group Chemical group 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 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
- 229930188620 butyrolactone Natural products 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- JLEKJZUYWFJPMB-UHFFFAOYSA-N ethyl 2-methoxyacetate Chemical compound CCOC(=O)COC JLEKJZUYWFJPMB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- JVSLVBYLHIRGJQ-JGVFFNPUSA-N n-[(1s,4r)-4-(hydroxymethyl)cyclopent-2-en-1-yl]acetamide Chemical compound CC(=O)N[C@H]1C[C@@H](CO)C=C1 JVSLVBYLHIRGJQ-JGVFFNPUSA-N 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- XYXFJNIUUWEUIJ-UHFFFAOYSA-N propan-2-yl 2-methoxyacetate Chemical compound COCC(=O)OC(C)C XYXFJNIUUWEUIJ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004673 propylcarbonyl group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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
- 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
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
-
- 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
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98124570 | 1998-12-23 | ||
| US14599999P | 1999-07-29 | 1999-07-29 | |
| PCT/EP1999/010382 WO2000039324A2 (fr) | 1998-12-23 | 1999-12-23 | Procede de production de derives 1-amino-4-(hydroxymetyl)-cyclopent-2-ene optiquement actifs |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20013037D0 NO20013037D0 (no) | 2001-06-19 |
| NO20013037L NO20013037L (no) | 2001-06-19 |
| NO326058B1 true NO326058B1 (no) | 2008-09-08 |
Family
ID=26149931
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20013037A NO326058B1 (no) | 1998-12-23 | 2001-06-19 | Fremgangsmate for fremstilling av optisk aktive 1-amino-4-(hydroksymetyl)-cyklopenten-2-en-derivater |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6524844B2 (fr) |
| EP (1) | EP1141374B1 (fr) |
| JP (1) | JP4633934B2 (fr) |
| KR (1) | KR100685195B1 (fr) |
| CN (1) | CN1189569C (fr) |
| AT (1) | ATE253125T1 (fr) |
| AU (1) | AU2102600A (fr) |
| CA (1) | CA2354382C (fr) |
| CZ (1) | CZ301107B6 (fr) |
| DE (1) | DE59907569D1 (fr) |
| DK (1) | DK1141374T3 (fr) |
| ES (1) | ES2211216T3 (fr) |
| HU (1) | HUP0104547A3 (fr) |
| IL (1) | IL143229A0 (fr) |
| MX (1) | MXPA01006428A (fr) |
| NO (1) | NO326058B1 (fr) |
| PL (1) | PL196857B1 (fr) |
| PT (1) | PT1141374E (fr) |
| SK (1) | SK285795B6 (fr) |
| WO (1) | WO2000039324A2 (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0104547A3 (en) * | 1998-12-23 | 2003-12-29 | Lonza Ag | Method for producing optically active 1-amino-4-(hydroxymethyl)-cyclopent-2-ene derivatives |
| GB0306267D0 (en) | 2003-03-19 | 2003-04-23 | Ineos Fluor Ltd | Process |
| WO2006117057A1 (fr) * | 2005-05-02 | 2006-11-09 | Dsm Fine Chemicals Austria Nfg Gmbh & Co Kg | Procede de fabrication d'acides e-(2s)- et (2r)-alkyl-5-halopento-4-ene-carboxyliques enrichis de façon enantiomerique ou de leurs esters |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2756790B2 (ja) * | 1988-07-18 | 1998-05-25 | 富士薬品工業株式会社 | 光学活性なシクロペンテノール誘導体の製造方法 |
| GB9108376D0 (en) * | 1991-04-19 | 1991-06-05 | Enzymatix Ltd | Cyclopentenes |
| CN1224697C (zh) * | 1996-05-30 | 2005-10-26 | 隆萨股份公司 | 氨基醇及其衍生物的制备方法 |
| SK284810B6 (sk) | 1997-05-13 | 2005-12-01 | Lonza Ag | Spôsob výroby (1S,4R)- alebo (1R,4S)-4-(2-amino-6-chlór-9-H- purín-9-yl)-2-cyklopentén-1-metanolu |
| CZ298144B6 (cs) * | 1997-11-27 | 2007-07-04 | Lonza Ag | Zpusob výroby (1S,4R)- nebo (1R,4S)-4-(2-amino-6-chlor-9-H-purin-9-yl)-2-cyklopenten-1-methanolu |
| HUP0104547A3 (en) * | 1998-12-23 | 2003-12-29 | Lonza Ag | Method for producing optically active 1-amino-4-(hydroxymethyl)-cyclopent-2-ene derivatives |
-
1999
- 1999-12-23 HU HU0104547A patent/HUP0104547A3/hu unknown
- 1999-12-23 IL IL14322999A patent/IL143229A0/xx active IP Right Grant
- 1999-12-23 AT AT99965556T patent/ATE253125T1/de active
- 1999-12-23 DE DE59907569T patent/DE59907569D1/de not_active Expired - Lifetime
- 1999-12-23 CN CNB998147133A patent/CN1189569C/zh not_active Expired - Fee Related
- 1999-12-23 CZ CZ20012168A patent/CZ301107B6/cs not_active IP Right Cessation
- 1999-12-23 SK SK881-2001A patent/SK285795B6/sk not_active IP Right Cessation
- 1999-12-23 AU AU21026/00A patent/AU2102600A/en not_active Abandoned
- 1999-12-23 WO PCT/EP1999/010382 patent/WO2000039324A2/fr active IP Right Grant
- 1999-12-23 EP EP99965556A patent/EP1141374B1/fr not_active Expired - Lifetime
- 1999-12-23 PL PL349388A patent/PL196857B1/pl not_active IP Right Cessation
- 1999-12-23 CA CA2354382A patent/CA2354382C/fr not_active Expired - Fee Related
- 1999-12-23 ES ES99965556T patent/ES2211216T3/es not_active Expired - Lifetime
- 1999-12-23 PT PT99965556T patent/PT1141374E/pt unknown
- 1999-12-23 DK DK99965556T patent/DK1141374T3/da active
- 1999-12-23 KR KR1020017007823A patent/KR100685195B1/ko not_active IP Right Cessation
- 1999-12-23 MX MXPA01006428A patent/MXPA01006428A/es not_active IP Right Cessation
- 1999-12-23 JP JP2000591213A patent/JP4633934B2/ja not_active Expired - Fee Related
-
2001
- 2001-06-19 NO NO20013037A patent/NO326058B1/no not_active IP Right Cessation
- 2001-06-22 US US09/888,068 patent/US6524844B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2211216T3 (es) | 2004-07-01 |
| HUP0104547A2 (hu) | 2002-03-28 |
| JP2003520018A (ja) | 2003-07-02 |
| SK285795B6 (sk) | 2007-08-02 |
| DE59907569D1 (de) | 2003-12-04 |
| CA2354382C (fr) | 2010-09-07 |
| WO2000039324A3 (fr) | 2000-09-21 |
| CN1189569C (zh) | 2005-02-16 |
| EP1141374B1 (fr) | 2003-10-29 |
| NO20013037D0 (no) | 2001-06-19 |
| US6524844B2 (en) | 2003-02-25 |
| NO20013037L (no) | 2001-06-19 |
| JP4633934B2 (ja) | 2011-02-16 |
| KR100685195B1 (ko) | 2007-02-22 |
| CN1352695A (zh) | 2002-06-05 |
| US20020042108A1 (en) | 2002-04-11 |
| CA2354382A1 (fr) | 2000-07-06 |
| ATE253125T1 (de) | 2003-11-15 |
| IL143229A0 (en) | 2002-04-21 |
| PT1141374E (pt) | 2004-03-31 |
| WO2000039324A2 (fr) | 2000-07-06 |
| CZ20012168A3 (cs) | 2001-11-14 |
| HUP0104547A3 (en) | 2003-12-29 |
| KR20010099861A (ko) | 2001-11-09 |
| SK8812001A3 (en) | 2002-01-07 |
| MXPA01006428A (es) | 2002-06-21 |
| DK1141374T3 (da) | 2004-02-16 |
| CZ301107B6 (cs) | 2009-11-11 |
| AU2102600A (en) | 2000-07-31 |
| EP1141374A2 (fr) | 2001-10-10 |
| PL349388A1 (en) | 2002-07-15 |
| PL196857B1 (pl) | 2008-02-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5223432A (en) | Process for preparing optically pure (S)-α-((tert-butylsulfonyl)methyl)hydrocinnamic acid using protease | |
| ES2249917T3 (es) | Resolucion de trans-2-(alcoxicarboniletil9-lactamas utiles en la sintesis de 1-(4-fluorofenil)-3(r)-3(s)-hidroxi-3-(4-fluorofenil)-propil)-4(s)-(4-hidroxifenil)-2-azetidinona. | |
| HU226473B1 (en) | Process for producing (1r,4s)- and (1s,4r)-1-amino-4-hydroxymethyl-2-cyclopentene | |
| AU717771B2 (en) | The bioresolution of n-acylazetidine-2-carboxylic acids | |
| NO326058B1 (no) | Fremgangsmate for fremstilling av optisk aktive 1-amino-4-(hydroksymetyl)-cyklopenten-2-en-derivater | |
| NZ250478A (en) | Enzymatic process for the stereoselective preparation of a heterobicyclic alcohol enantiomer and use as an intermediate to prepare flesinoxan | |
| Miyazawa et al. | Resolution of racemic carboxylic acids via the lipase‐catalyzed irreversible transesterification of vinyl esters | |
| IL143229A (en) | Method for producing optically active 1-amino-4-(hydroxymethyl)-cyclopent-2-ene derivatives | |
| JP2687789B2 (ja) | 光学活性３−フェニルグリシッド酸エステル類化合物の製法 | |
| Musidlowska-Persson et al. | Substrate specificity of the γ-isoenzyme of recombinant pig liver esterase towards acetates of secondary alcohols | |
| US6455302B1 (en) | Method for optically resolving a racemic α-substituted heterocyclic carboxylic acid using enzyme | |
| US5476965A (en) | Enzymatic resolution of substituted 2-methyl-propionic acid | |
| KR100758512B1 (ko) | 효소적 방법에 의한 광학활성3-히드록시-3-페닐프로피온산과 광학활성3-아실옥시-3-페닐프로피온산의 제조 방법 | |
| JPH10337197A (ja) | 光学活性３−ハイドロキシテトラハイドロフランの製造方法 | |
| JPH08259552A (ja) | 光学活性フェニルグリシッド酸エステル類の製法 | |
| JP3935992B2 (ja) | 光学活性３−クロロラクトニトリル及びそのエステル並びにそれらの製造方法 | |
| JP4746019B2 (ja) | 光学活性β−シアノイソ酪酸類及びその製造方法 | |
| US20030143698A1 (en) | Process for the enzymatic preparation of enantiopure 1, 3-dioxolan-4-one and 1,3-oxathiolan-5-one derivatives | |
| JP4565672B2 (ja) | 光学活性β−シアノイソ酪酸類及びその製造方法 | |
| JPH04356195A (ja) | アゼチジノン誘導体の製造法 | |
| JP3960667B2 (ja) | β−カルバモイルイソ酪酸類及びその製造方法 | |
| US20030109029A1 (en) | Process for the preparation of enantiomerically pure tertiary ss-hydroxycarboxylic acids or their esters | |
| JPH0856687A (ja) | （ｓ）−３−（２−チエニルチオ）ブタン酸の製造法 | |
| JPH05192188A (ja) | 光学活性な置換酪酸またはそのエステル誘導体の製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |