DD272475A5 - Verfahren zur enantioselektiven reduktion von ketonen - Google Patents

Verfahren zur enantioselektiven reduktion von ketonen Download PDF

Info

Publication number: DD272475A5
Authority: DD; German Democratic Republic
Prior art keywords: atoms; compounds; methyl; alkyl; amino
Prior art date: 1987-07-22

Application number

DD88318118A

Other languages

German (de)

English (en)

Inventor

Hans-Eckart Radunz

Harry Schwartz

Martin Heinrich

Original Assignee

��@��@��@��@��@��k��

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.)

1987-07-22

Filing date

1988-07-20

Publication date

1989-10-11

1988-07-20 Application filed by ��@��@��@��@��@��k�� filed Critical ��@��@��@��@��@��k��

1989-10-11 Publication of DD272475A5 publication Critical patent/DD272475A5/de

Links

230000009467 reduction Effects 0.000 title claims abstract description 25
238000000034 method Methods 0.000 title claims abstract description 17
150000002576 ketones Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 11
244000005700 microbiome Species 0.000 claims abstract description 11
125000000468 ketone group Chemical group 0.000 claims abstract description 10
150000003333 secondary alcohols Chemical class 0.000 claims abstract description 10
239000007858 starting material Substances 0.000 claims abstract description 6
-1 9-fluorenylmethoxycarbonyl Chemical group 0.000 claims description 112
125000004432 carbon atom Chemical group C* 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
239000002461 renin inhibitor Substances 0.000 claims description 6
238000003786 synthesis reaction Methods 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 5
229940086526 renin-inhibitors Drugs 0.000 claims description 5
125000004103 aminoalkyl group Chemical group 0.000 claims description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
150000001602 bicycloalkyls Chemical group 0.000 claims description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims 1
238000006722 reduction reaction Methods 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
240000004808 Saccharomyces cerevisiae Species 0.000 description 14
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 14
210000004027 cell Anatomy 0.000 description 14
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 11
239000008103 glucose Substances 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
238000011534 incubation Methods 0.000 description 9
210000005253 yeast cell Anatomy 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
241001276012 Wickerhamomyces ciferrii Species 0.000 description 6
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
241000878745 Cyberlindnera saturnus Species 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
241000235648 Pichia Species 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
238000000746 purification Methods 0.000 description 5
239000000499 gel Substances 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
238000000926 separation method Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
VQTXXGADMWQAGH-BQBZGAKWSA-N CC(C)C[C@H](N=O)[C@@H](O)CC(O)=O Chemical compound CC(C)C[C@H](N=O)[C@@H](O)CC(O)=O VQTXXGADMWQAGH-BQBZGAKWSA-N 0.000 description 3
241000222120 Candida <Saccharomycetales> Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 3
239000001888 Peptone Substances 0.000 description 3
108010080698 Peptones Proteins 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
229940041514 candida albicans extract Drugs 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
238000001514 detection method Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000000605 extraction Methods 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
235000019319 peptone Nutrition 0.000 description 3
239000000047 product Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000012138 yeast extract Substances 0.000 description 3
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 2
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
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 description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
JBGHSZNXBMVRHU-UEWDXFNNSA-N 5-o-tert-butyl 1-o-methyl (4s)-2-amino-4-benzyl-3-oxopentanedioate Chemical compound COC(=O)C(N)C(=O)[C@@H](C(=O)OC(C)(C)C)CC1=CC=CC=C1 JBGHSZNXBMVRHU-UEWDXFNNSA-N 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
244000286779 Hansenula anomala Species 0.000 description 2
235000014683 Hansenula anomala Nutrition 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
238000005273 aeration Methods 0.000 description 2
239000011324 bead Substances 0.000 description 2
239000006285 cell suspension Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000000855 fermentation Methods 0.000 description 2
230000004151 fermentation Effects 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
210000001822 immobilized cell Anatomy 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
MPVVGXNZMOJLQI-QWRGUYRKSA-N methyl (3s,4s)-4-amino-3-hydroxy-5-phenylpentanoate Chemical compound COC(=O)C[C@H](O)[C@@H](N)CC1=CC=CC=C1 MPVVGXNZMOJLQI-QWRGUYRKSA-N 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
239000012071 phase Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000011084 recovery Methods 0.000 description 2
230000000284 resting effect Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 description 1
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 description 1
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 description 1
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 description 1
125000006482 3-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(I)=C1[H])C([H])([H])* 0.000 description 1
125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
125000006483 4-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1I)C([H])([H])* 0.000 description 1
125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 1
NYKKEASRZQSNJN-KGEZELFJSA-N 5-o-tert-butyl 1-o-methyl (3s,4s)-2-amino-3-hydroxy-4-[(4-methylcyclohexyl)methyl]pentanedioate Chemical compound COC(=O)C(N)[C@@H](O)[C@@H](C(=O)OC(C)(C)C)CC1CCC(C)CC1 NYKKEASRZQSNJN-KGEZELFJSA-N 0.000 description 1
DMQNROZYHPOVTP-HPNRGHHYSA-N 5-o-tert-butyl 1-o-methyl (3s,4s)-2-amino-4-benzyl-3-hydroxypentanedioate Chemical compound COC(=O)C(N)[C@@H](O)[C@@H](C(=O)OC(C)(C)C)CC1=CC=CC=C1 DMQNROZYHPOVTP-HPNRGHHYSA-N 0.000 description 1
KIDMENOBQYVETJ-RFPFOJJUSA-N 5-o-tert-butyl 1-o-methyl (4s)-2-amino-4-[(4-methylcyclohexyl)methyl]-3-oxopentanedioate Chemical compound COC(=O)C(N)C(=O)[C@@H](C(=O)OC(C)(C)C)CC1CCC(C)CC1 KIDMENOBQYVETJ-RFPFOJJUSA-N 0.000 description 1
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-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
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
241001237431 Anomala Species 0.000 description 1
ZLXHNGNTLWPPSB-YFXXHVASSA-N C(C)(C)(C)C1CCC(CC1)C[C@@H](C(C(C(=O)O)N)=O)C(=O)OC(C)(C)C Chemical compound C(C)(C)(C)C1CCC(CC1)C[C@@H](C(C(C(=O)O)N)=O)C(=O)OC(C)(C)C ZLXHNGNTLWPPSB-YFXXHVASSA-N 0.000 description 1
101710088194 Dehydrogenase Proteins 0.000 description 1
108020005199 Dehydrogenases Proteins 0.000 description 1
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
229910010082 LiAlH Inorganic materials 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
241000235070 Saccharomyces Species 0.000 description 1
241000582914 Saccharomyces uvarum Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
241000235152 Williopsis Species 0.000 description 1
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000008272 agar Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
235000008206 alpha-amino acids Nutrition 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000010923 batch production Methods 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
239000000872 buffer Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-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
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000001963 growth medium Substances 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
125000005842 heteroatom Chemical group 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
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229960000367 inositol Drugs 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
150000002690 malonic acid derivatives Chemical class 0.000 description 1
QCZPJJIXHJSOMY-YFKPBYRVSA-N methyl (2S)-2-hydroxypentanoate Chemical compound CCC[C@H](O)C(=O)OC QCZPJJIXHJSOMY-YFKPBYRVSA-N 0.000 description 1
ZTVRYIAJRPPIPG-JTQLQIEISA-N methyl (4s)-4-amino-3-oxo-5-phenylpentanoate Chemical compound COC(=O)CC(=O)[C@@H](N)CC1=CC=CC=C1 ZTVRYIAJRPPIPG-JTQLQIEISA-N 0.000 description 1
230000007483 microbial process Effects 0.000 description 1
235000016337 monopotassium tartrate Nutrition 0.000 description 1
125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 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
239000001301 oxygen Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical compound [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 1
229940086065 potassium hydrogentartrate Drugs 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
235000019394 potassium persulphate Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000006228 supernatant Substances 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
238000004809 thin layer chromatography Methods 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 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
- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
- C12P7/26—Ketones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
- 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
- C12P13/002—Nitriles (-CN)
- 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
- C12P13/008—Preparation of nitrogen-containing organic compounds containing a N-O bond, e.g. nitro (-NO2), nitroso (-NO)
- 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
- 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- 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
- C12P41/002—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by oxidation/reduction reactions
- 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
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/911—Microorganisms using fungi
- Y10S435/93—Hansenula
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/911—Microorganisms using fungi
- Y10S435/94—Saccharomyces
- Y10S435/942—Saccharomyces cerevisiae

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Zoology (AREA)
Wood Science & Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
Microbiology (AREA)
Genetics & Genomics (AREA)
Analytical Chemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)
Peptides Or Proteins (AREA)

DD88318118A 1987-07-22 1988-07-20 Verfahren zur enantioselektiven reduktion von ketonen DD272475A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19873724197 DE3724197A1 (de)	1987-07-22	1987-07-22	Verfahren zur reduktion von ketonen

Publications (1)

Publication Number	Publication Date
DD272475A5 true DD272475A5 (de)	1989-10-11

Family

ID=6332081

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88318118A DD272475A5 (de)	1987-07-22	1988-07-20	Verfahren zur enantioselektiven reduktion von ketonen

Country Status (14)

Country	Link
US (1)	US5026642A (da)
EP (1)	EP0300287B1 (da)
JP (1)	JPS6455187A (da)
KR (1)	KR890002409A (da)
AR (1)	AR240064A1 (da)
AT (1)	ATE84317T1 (da)
AU (1)	AU628289B2 (da)
DD (1)	DD272475A5 (da)
DE (2)	DE3724197A1 (da)
DK (1)	DK409388A (da)
ES (1)	ES2043738T3 (da)
FI (1)	FI883457A7 (da)
HU (1)	HU203905B (da)
ZA (1)	ZA885365B (da)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5232853A (en) *	1989-12-28	1993-08-03	Takeda Chemical Industries, Ltd.	Method for producing (2r,3s)-3-hydroxy-2-methylbutyrate by microbial reduction
US5215919A (en) *	1991-02-25	1993-06-01	Takeda Chemical Industries, Ltd.	Process for producing optically active 2-hydroxycycloalkanecarboxylic acid esters using microbially derived reductase
WO1993007289A1 (en) *	1991-10-04	1993-04-15	Schering Corporation	ENZYMATIC SYNTHESIS OF CHIRAL α-HYDROXYKETONES AND DERIVATIVES
DE4209022B4 (de) *	1992-03-20	2006-01-19	Forschungszentrum Jülich GmbH	Verfahren zur enzymatischen Herstellung von sekundären (S)-Alkoholen
US5324662A (en) *	1992-05-15	1994-06-28	E. R. Squibb & Sons, Inc.	Stereoselective microbial or enzymatic reduction of 3,5-dioxo esters to 3-hydroxy-5-oxo, 3-oxo-5-hydroxy, and 3,5-dihydroxy esters
CA2103932A1 (en) *	1992-11-05	1994-05-06	Ramesh N. Patel	Stereoselective reduction of ketones
GB9512837D0 (en) *	1995-06-23	1995-08-23	Zeneca Ltd	reduction of ketone groups
WO1999057279A1 (en)	1998-05-07	1999-11-11	Doosan Corporation	Plasmid for gene expression in pichia ciferrii and transformation method using the same
KR100411685B1 (ko) *	2001-10-31	2003-12-18	(주)그린앤크린	대두지방산과 레시틴을 이용한 활성 수용성 천연세제조성물 및 그 제조방법
US10784121B2 (en)	2016-08-15	2020-09-22	Xilinx, Inc.	Standalone interface for stacked silicon interconnect (SSI) technology integration

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4478826A (en) *	1981-10-08	1984-10-23	Merck & Co., Inc.	Renin inhibitory peptides
CA1258748A (en) *	1981-10-08	1989-08-22	Daniel F. Veber	Renin inhibitory peptides
EP0104041B1 (en) *	1982-09-15	1988-07-27	Aktiebolaget Hässle	Enzyme inhibitors
US4650661A (en) *	1982-09-15	1987-03-17	Aktiebolaget Hassle	Enzyme inhibitors
US4477440A (en) *	1983-09-14	1984-10-16	Merck & Co., Inc.	Renin inhibitors containing an n-terminal disulfide cycle
KR870005013A (ko) *	1985-11-29	1987-06-04	가와무라 요시부미	레닌-억제 올리고펩티드, 그의 제조방법 및 용도

1987
- 1987-07-22 DE DE19873724197 patent/DE3724197A1/de not_active Withdrawn
1988
- 1988-06-21 AU AU18232/88A patent/AU628289B2/en not_active Ceased
- 1988-07-08 AT AT88110912T patent/ATE84317T1/de not_active IP Right Cessation
- 1988-07-08 ES ES88110912T patent/ES2043738T3/es not_active Expired - Lifetime
- 1988-07-08 DE DE8888110912T patent/DE3877275D1/de not_active Expired - Fee Related
- 1988-07-08 EP EP88110912A patent/EP0300287B1/de not_active Expired - Lifetime
- 1988-07-19 KR KR1019880009015A patent/KR890002409A/ko not_active Withdrawn
- 1988-07-20 DD DD88318118A patent/DD272475A5/de not_active IP Right Cessation
- 1988-07-20 AR AR311459A patent/AR240064A1/es active
- 1988-07-21 DK DK409388A patent/DK409388A/da not_active Application Discontinuation
- 1988-07-21 HU HU883801A patent/HU203905B/hu not_active IP Right Cessation
- 1988-07-21 JP JP63180461A patent/JPS6455187A/ja active Pending
- 1988-07-21 FI FI883457A patent/FI883457A7/fi not_active IP Right Cessation
- 1988-07-22 US US07/223,051 patent/US5026642A/en not_active Expired - Fee Related
- 1988-07-22 ZA ZA885365A patent/ZA885365B/xx unknown

Also Published As

Publication number	Publication date
ZA885365B (en)	1989-03-29
EP0300287B1 (de)	1993-01-07
FI883457A7 (fi)	1989-01-23
AU1823288A (en)	1989-01-27
JPS6455187A (en)	1989-03-02
DE3877275D1 (de)	1993-02-18
ATE84317T1 (de)	1993-01-15
DK409388D0 (da)	1988-07-21
AU628289B2 (en)	1992-09-17
KR890002409A (ko)	1989-04-10
US5026642A (en)	1991-06-25
EP0300287A3 (en)	1989-05-03
FI883457A0 (fi)	1988-07-21
EP0300287A2 (de)	1989-01-25
DK409388A (da)	1989-01-23
AR240064A1 (es)	1990-01-31
DE3724197A1 (de)	1989-02-02
HUT47642A (en)	1989-03-28
HU203905B (en)	1991-10-28
ES2043738T3 (es)	1994-01-01

Legal Events

Date	Code	Title	Description
2000-02-17	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69614174T2 (de)	2002-04-11	Verfahren zur Herstellung von optisch-aktiven Gamma-substituierte-Hydroxy-Buttersäure-Ester
DE69420754T2 (de)	2000-01-13	Verfahren zur Herstellung von Phenylgruppe enthaltende optisch-aktiven Alpha-Hydroxycarbonsäuren
EP0300287B1 (de)	1993-01-07	Verfahren zur Reduktion von Ketonen
DE69432679T2 (de)	2004-02-19	Verfahren zur Herstellung von optisch aktiven 2-Amino-1-phenylethanol Derivaten
EP1177310B1 (de)	2005-01-26	Verfahren zur herstellung von l-phosphinothricin durch enzymatische transaminierung mit aspartat
DE3875953T2 (de)	1993-06-03	Verfahren zur herstellung von organischen chemischen verbindungen.
DE69329719T2 (de)	2001-07-05	Stereoselektive mikrobielle oder enzymatische Reduktion von 3,5-Dioxoestern zu 3,5-Dihydroxyestern
DE3001303A1 (de)	1981-07-23	Optisch aktive phenylpropan-derivate, ihre herstellung und verwendung
AT407397B (de)	2001-02-26	(s)-hydroxynitrillyasen mit verbesserter substratakzeptanz und deren verwendung
DE69305748T2 (de)	1997-03-13	Enzymatisches asymetrisches reduktionsverfahren zur herstellung von 4h thieno (2,3-6) thiopyren derivaten.
WO1997045529A1 (de)	1997-12-04	Verfahren zur herstellung von aminoalkoholen und derivaten davon
EP0400638B1 (de)	1994-10-05	Verfahren zur Herstellung von D-alpha-Aminocarbonsäuren
EP0377083B1 (de)	1993-09-22	Verfahren zur Herstellung von L-alpha-Aminosäuren
EP1200601B1 (de)	2006-03-08	Verfahren zur herstellung von l-aminosäuren aus ihren racemischen n-acetyl-d,l-derivaten durch enzymatische racemat-spaltung mittels isolierter, rekombinanter enzyme
EP0745678A2 (de)	1996-12-04	Neuer Mikroorganismus, dessen Verwendung und Verfahren zur Herstellung von L-Alpha-Aminosäuren
DE69730444T2 (de)	2005-09-15	Verfahren zur herstellung optisch aktiven n-benzyl-3-pyrrolidinols
EP0502525A1 (de)	1992-09-09	Biotechnologisches Verfahren zur Herstellung von S-(+)-2,2-Dimethylcyclopropancarboxamid und R-(-)-2,2-Dimethylcyclopropancarbonsäure
EP0581250A2 (de)	1994-02-02	Verfahren zur Biotechnischen Herstellung von L-Thienylalaninen in enantiomerenreiner Form aus 2-Hydroxy-3-thienyl-acrylsäuren und ihre Verwendung
DE69529514T2 (de)	2003-11-20	Verfahren zur herstellung von (r)-2-amino-1-phenylethanol oder seinen halogenierten derivaten, verfahren zur herstellung von optisch aktivem phenylserin und seinen halogenierten derivaten, und die neuartige verbindung 3-(3-chlorophenyl)serin
DE60010013T2 (de)	2005-03-31	Verfahren zur Herstellung von optisch aktivem 1,2,4-Butantriol und optisch aktivem 3-Hydroxy-gamma-butyrolacton mittels Mikroorganismen
DE602004005947T2 (de)	2008-01-17	Verfahren zur Herstellung einer optisch aktiven Octahydro-1H-Indol-2-Carbonsäure
FR2508766A1 (fr)	1983-01-07	Nouvelle substance antifongique obtenue a partir d'une souche de bacillus subtilis, son procede d'obtention et ses applications comme antifongique
DE19942812A1 (de)	2001-03-15	Verfahren zur Herstellung von D-(3'-Pyridyl)-alanin
DE1900492C (da)
DE69329451T2 (de)	2001-04-19	Verfahren zur Herstellung von L-3,4-Dihydroxyphenylalanin