Desymmetrization of meso-cyclopenten-cis-1,4-diol to 4-(R)-hydroxycyclopent-2-en-1-(S)-acetate by irreversible transesterification using Chirazyme®

被引:15
作者
Ghorpade, SR [1 ]
Kharul, RK [1 ]
Joshi, RR [1 ]
Kalkote, UR [1 ]
Ravindranathan, T [1 ]
机构
[1] Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India
关键词
D O I
10.1016/S0957-4166(99)00068-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The parameter optimization study for the desymmetrization of meso-cyclopenten-1,4-diol 1 through irreversible transesterification using an immobilized lipase from Mucor meihei, i.e., Lipozyme(R)/Chirazyme(R) is presented. The enzyme was studied for the transesterification of 1 in various organic solvents by varying reaction parameters such as the nature of acyl donor, temperature, enzyme quantity etc., to afford optically active 4-(R)-hydroxycyclopent-2-en-1-(S)-acetate 2 of >98% enantiomeric excess in >60% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:891 / 899
页数:9
相关论文
共 41 条
[2]   Chemoenzymatic synthesis of a versatile cyclopentenone: (+)-(3aS,6aS)-2,2-dimethyl-3a beta,6a beta-dihydro-4H-cyclopenta-1,3-dioxol-4-one [J].
Biadatti, T ;
Esker, JL ;
Johnson, CR .
TETRAHEDRON-ASYMMETRY, 1996, 7 (08) :2313-2320
[3]   ENZYME CATALYZED-HYDROLYSIS OF DIALKYLATED PROPANEDIOIC ACID DIESTERS, SYNTHESIS OF OPTICALLY PURE (S)-ALPHA-METHYLPHENYLALANINE, (S)-ALPHA-METHYLTYROSINE AND (S)-ALPHA-METHYL-3,4-DIHYDROXYPHENYLALAINE [J].
BJORKLING, F ;
BOUTELJE, J ;
GATENBECK, S ;
HULT, K ;
NORIN, T .
TETRAHEDRON LETTERS, 1985, 26 (40) :4957-4958
[4]   THE EFFECT OF DIMETHYLSULFOXIDE ON THE ENANTIOSELECTIVITY IN THE PIG-LIVER ESTERASE CATALYZED-HYDROLYSIS OF DIALKYLATED PROPANEDIOIC ACID DIMETHYL ESTERS [J].
BJORKLING, F ;
BOUTELJE, J ;
GATENBECK, S ;
HULT, K ;
NORIN, T ;
SZMULIK, P .
BIOORGANIC CHEMISTRY, 1986, 14 (02) :176-181
[5]   Resolution of cis-4-O-TBS-2-cyclopenten-1,4-diol [J].
Curran, TT ;
Hay, DA .
TETRAHEDRON-ASYMMETRY, 1996, 7 (10) :2791-2792
[6]   A HIGHLY ENANTIOSELECTIVE HYDROLYSIS OF CIS-3,5-DIACETOXYCYCLOPENT-1-ENE - AN ENZYMATIC PREPARATION OF 3(R)-ACETOXY-5(S)-HYDROXYCYCLOPENT-1-ENE [J].
DEARDORFF, DR ;
MATTHEWS, AJ ;
MCMEEKIN, DS ;
CRANEY, CL .
TETRAHEDRON LETTERS, 1986, 27 (11) :1255-1256
[7]   A PALLADIUM-CATALYZED ROUTE TO MONOPROTECTED AND DIPROTECTED CIS-2-CYCLOPENTENE-1,4-DIOLS [J].
DEARDORFF, DR ;
MYLES, DC ;
MACFERRIN, KD .
TETRAHEDRON LETTERS, 1985, 26 (46) :5615-5618
[8]  
DEARDORFF DR, 1995, ORG SYNTH, P73
[9]   Significant effect of acyl groups on enantioselectivity in lipase-catalyzed transesterifications [J].
Ema, T ;
Maeno, S ;
Takaya, Y ;
Sakai, T ;
Utaka, M .
TETRAHEDRON-ASYMMETRY, 1996, 7 (03) :625-628
[10]   HOW CAN THE SOLVENT AFFECT ENZYME ENANTIOSELECTIVITY [J].
FITZPATRICK, PA ;
KLIBANOV, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (08) :3166-3171