3-HYDROXYGLUTARATE AND BETA-EPOXY, GAMMA-EPOXY ESTERS AS SUBSTRATES FOR PIG-LIVER ESTERASE (PLE) AND ALPHA-CHYMOTRYPSIN

被引：49

作者：

MOHR, P ^{[1
]}

ROSSLEIN, L ^{[1
]}

TAMM, C ^{[1
]}

机构：

[1] UNIV BASEL, INST ORGAN CHEM, ST JOHANNS RING 19, CH-4056 BASEL, SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1987年 / 70卷 / 01期

关键词：

D O I：

10.1002/hlca.19870700118

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The pH dependence of the .alpha.-chymotrypsin-catalyzed hydrolysis of dimethyl 3-hydroxyglutarate (3) has been studied. The e.e. was determined by HPLC analysis of diastereoisomeric camphanoic-acid derivatives. Kinetic resolution of the .beta.,.gamma.-epoxy esters 10 and 24 by pig liver esterase has been shown to provide an alternative access to chiral .beta.-hydroxy esters and acids of high optical purity. By this latter method, the unnatural enantiomer of .gamma.-amino-.beta.-hydroxybutyric acid (GABOB) has been synthesized. Finally, dimethyl meso-3,4-epoxyadipate (19) was hydrolyzed by pig liver esterase with almost 100% selectivity.

引用

页码：142 / 152

页数：11

共 5 条

[1] KINETIC RESOLUTION OF RACEMIC BETA,GAMMA-EPOXY ESTERS WITH PIG-LIVER ESTERASE (PLE, EC 3.1.1.1.)
MOHR, P
ROSSLEIN, L
TAMM, C
TETRAHEDRON LETTERS, 1989, 30 (19) : 2513 - 2516
[2] STEREOSELECTIVE HYDROLYSIS OF THE DIMETHYL 4,5-EPOXY-1,2-CIS-CYCLOHEXANEDICARBOXYLATES WITH PIG-LIVER ESTERASE (PLE)
KUHN, T
TAMM, C
RIESEN, A
ZEHNDER, M
TETRAHEDRON LETTERS, 1989, 30 (06) : 693 - 696
[3] SYNTHESIS OF OPTICALLY-ACTIVE BETA,GAMMA-EPOXY ALCOHOLS AND SECONDARY ALLYLIC ALCOHOLS VIA DIASTEREOSELECTIVE ADDITION OF ALPHA-TRIMETHYLSILYL-ALPHA,BETA-EPOXY ALDEHYDES WITH ORGANOMETALLIC COMPOUNDS
TAKEDA, Y
MATSUMOTO, T
SATO, F
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (24): : 4728 - 4731
[4] SMI2-INDUCED HIGHLY REGIOSELECTIVE REDUCTION OF ALPHA,BETA-EPOXY ESTERS AND GAMMA,DELTA-EPOXY-ALPHA,BETA-UNSATURATED ESTERS - AN EFFICIENT ROUTE TO OPTICALLY-ACTIVE BETA-HYDROXY AND DELTA-HYDROXY ESTERS
OTSUBO, K
INANAGA, J
YAMAGUCHI, M
TETRAHEDRON LETTERS, 1987, 28 (38) : 4437 - 4440
[5] ENANTIOSELECTIVE HYDROLYSIS OF DIMETHYL 2-ALPHA,3-ALPHA-[(DIMETHYLMETHYLENE)DIOXY]-5-BETA-HYDROXY-1-BETA,4-BETA-CYCLOPENTANEDICARBOXYLATE WITH PIG-LIVER ESTERASE - STEREOSELECTIVE SYNTHESIS OF METHYL 2(R),3(S)-[(DIMETHYLMETHYLENE)DIOXY]-5(R)-HYDROXY-1(S)-CARBOXY-4(R)-CYCLOPENTANECARBOXYLATE - A CYCLOPENTANE SYNTHON WITH ALL RING ATOMS CHIRAL
ZEMLICKA, J
CRAINE, LE
HEEG, MJ
OLIVER, JP
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05): : 937 - 942

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