PPL-CATALYZED RESOLUTION OF 1,2-DIOLS AND 1,3-DIOLS IN METHYL PROPIONATE AS SOLVENT - AN APPLICATION OF THE TANDEM USE OF ENZYMES

被引：45

作者：

JANSSEN, AJM ^{[1
]}

KLUNDER, AJH ^{[1
]}

ZWANENBURG, B ^{[1
]}

机构：

[1] CATHOLIC UNIV NIJMEGEN,NSR CTR MOLEC STRUCT DESIGN & SYNTHESIS,DEPT ORGAN CHEM,6525 ED NIJMEGEN,NETHERLANDS

来源：

TETRAHEDRON | 1991年 / 47卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(01)89742-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Porcine Pancreatic Lipase (PPL)-catalyzed transesterification of 1-phenyl-1,2-ethanediol 1, 2-phenyl-1,2-propanediol 2, 1,2-decanediol 3, 1,2-pentanediol 4, 1,2-butanediol 5, 1,2-propanediol 6 and 1,3-butanediol 7 in methyl propionate as solvent was evaluated. In all substrates, the primary hydroxy group is esterified exclusively. The enantioselectivity displayed in this PPL-catalyzed reaction is moderate. The enantiomeric excess of diol (-)-1 is enhanced by subjecting propionate (-)-8, with a moderate ee (obtained by a PPL-catalyzed esterification of racemic 1 in methyl propionate), to an enzyme-catalyzed hydrolysis (tandem principle).

引用

页码：7409 / 7416

页数：8

共 32 条

[1] ENZYME CATALYZED PREPARATION OF 6-O-ACYLGLUCOPYRANOSIDES [J].

ADELHORST, K ;

BJORKLING, F ;

GODTFREDSEN, SE ;

KIRK, O .

SYNTHESIS-STUTTGART, 1990, (02) :112-115

[2] ENZYMATIC ESTER HYDROLYSIS AND SYNTHESIS - 2 APPROACHES TO CYCLOALKANE DERIVATIVES OF HIGH ENANTIOMERIC PURITY [J].

ADER, U ;

BREITGOFF, D ;

KLEIN, P ;

LAUMEN, KE ;

SCHNEIDER, MP .

TETRAHEDRON LETTERS, 1989, 30 (14) :1793-1796

[3]

ARPESELLA L, 1955, GAZZ CHIM ITAL, V85, P1354

[4] AN EFFICIENT ENANTIOSELECTIVE PREPARATION OF 2-SUBSTITUTED-3-HYDROXYPROPIONIC ACIDS VIA CHEMOENZYMATIC REACTION [J].

ATSUUMI, S ;

NAKANO, M ;

KOIKE, Y ;

TANAKA, S ;

OHKUBO, M ;

YONEZAWA, T ;

FUNABASHI, H ;

HASHIMOTO, J ;

MORISHIMA, H .

TETRAHEDRON LETTERS, 1990, 31 (11) :1601-1604

[5] ENZYMATIC RESOLUTION OF 2,3-EPOXYALCOHOLS, INTERMEDIATES IN THE SYNTHESIS OF THE GYPSY-MOTH SEX-PHEROMONE [J].

BIANCHI, D ;

CABRI, W ;

CESTI, P ;

FRANCALANCI, F ;

RAMA, F .

TETRAHEDRON LETTERS, 1988, 29 (20) :2455-2458

[6] ANHYDRIDES AS ACYLATING AGENTS IN LIPASE-CATALYZED STEREOSELECTIVE ESTERIFICATION OF RACEMIC ALCOHOLS [J].

BIANCHI, D ;

CESTI, P ;

BATTISTEL, E .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5531-5534

[7] 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

[8] ENZYMATIC-SYNTHESIS OF VARIOUS 1'-O-SUCROSE AND 1-O-FRUCTOSE ESTERS [J].

CARREA, G ;

RIVA, S ;

SECUNDO, F ;

DANIELI, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05) :1057-1061

[9] 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

[10] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].

CHEN, CS ;

FUJIMOTO, Y ;

GIRDAUKAS, G ;

SIH, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299

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