Kinetic resolution of 2-acylated-1,2-diols by lipase-catalyzed enantiomer selective acylation

被引:19
作者
Egri, G
BaitzGacs, E
Poppe, L
机构
[1] TECH UNIV BUDAPEST,DEPT ORGAN CHEM TECHNOL,H-1521 BUDAPEST,HUNGARY
[2] HUNGARIAN ACAD SCI,CENT RES INST CHEM,H-1525 BUDAPEST,HUNGARY
关键词
D O I
10.1016/0957-4166(96)00161-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Enantiomer selectivity of lipase catalyzed acylation of 2-acylated 1,2-diols was studied. First, acylation of 2-acetoxyheptan-1-ol rac-3b with vinyl acetate was investigated by varying the enzyme and the solvent, showing the highest enantiomer selectivity by using lipase from Pseudomonas fluorescens (PfL) in hexane-vinyl acetate (VA). We have found varying or even reversed enantiomer selectivity for different secondary acyl moieties in 2-acyloxyheptan-1-ols rac-3bA-F. Next, all six possible types of enantiomer selective biotransformations (hydrolysis of diacetate and the two kinds of monoacetetes; acylation of diol and the two kinds of monoacetates) were compared on two model diols rac-4b,d. Among the transformations investigated, acetylation of secondary monoacetates rac-3b,d showed the highest enantiomer selectivity. Finally, PfL catalyzed acetylations of several 2-acetylated 1,2-diols rac-3a-g were investigated under our optimum conditions. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:1437 / 1448
页数:12
相关论文
共 26 条
[1]  
BERGSTEIN W, 1981, SYNTHESIS-STUTTGART, P76
[2]   ENZYMATIC RESOLUTION OF 1,2-DIOLS - PREPARATION OF OPTICALLY PURE DROPROPIZINE [J].
BIANCHI, D ;
BOSETTI, A ;
CESTI, P ;
GOLINI, P .
TETRAHEDRON LETTERS, 1992, 33 (22) :3231-3234
[3]   PREPARATIVE PRODUCTION OF OPTICALLY-ACTIVE ESTERS AND ALCOHOLS USING ESTERASE-CATALYZED STEREOSPECIFIC TRANS-ESTERIFICATION IN ORGANIC MEDIA [J].
CAMBOU, B ;
KLIBANOV, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (09) :2687-2692
[4]   PREPARATIVE REGIOSELECTIVE ACYLATION OF GLYCOLS BY ENZYMATIC TRANSESTERIFICATION IN ORGANIC-SOLVENTS [J].
CESTI, P ;
ZAKS, A ;
KLIBANOV, AM .
APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, 1985, 11 (05) :401-407
[5]  
CHATTOPADHYAY S, 1990, B SOC CHIM FR, P108
[6]   BAKERS YEAST-MEDIATED REDUCTION OF ALPHA-HYDROXY KETONES AND DERIVATIVES - THE STERIC COURSE OF THE BIOTRANSFORMATION [J].
FERRABOSCHI, P ;
GRISENTI, P ;
MANZOCCHI, A ;
SANTANIELLO, E .
TETRAHEDRON, 1994, 50 (35) :10539-10548
[7]   HIGH-YIELD PRODUCTION OF OPTICALLY-ACTIVE 1,2-DIOLS FROM THE CORRESPONDING RACEMATES BY MICROBIAL STEREOINVERSION [J].
HASEGAWA, J ;
OGURA, M ;
TSUDA, S ;
MAEMOTO, S ;
KUTSUKI, H ;
OHASHI, T .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (07) :1819-1827
[8]   REGIOSELECTIVE AND ENANTIOSELECTIVE ESTERIFICATIONS OF POLYOXYGENATED COMPOUNDS CATALYZED BY LIPASES [J].
HERRADON, B ;
CUETO, S ;
MORCUENDE, A ;
VALVERDE, S .
TETRAHEDRON-ASYMMETRY, 1993, 4 (05) :845-864
[9]   ASYMMETRIC HYDROLYSIS OF ESTERS BY BIOCHEMICAL METHODS .3. ASYMMETRIC HYDROLYSIS OF "(+/-)-1,2-DIACETOXY-3-CHLOROPROPANE AND ITS RELATED-COMPOUNDS WITH LIPASE - SYNTHESIS OF OPTICALLY PURE (S)-PROPRANOLOL [J].
IRIUCHIJIMA, S ;
KOJIMA, N .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1982, 46 (05) :1153-1157
[10]   PPL-CATALYZED RESOLUTION OF 1,2-DIOLS AND 1,3-DIOLS IN METHYL PROPIONATE AS SOLVENT - AN APPLICATION OF THE TANDEM USE OF ENZYMES [J].
JANSSEN, AJM ;
KLUNDER, AJH ;
ZWANENBURG, B .
TETRAHEDRON, 1991, 47 (35) :7409-7416