ENZYMES IN ORGANIC-SYNTHESIS .48. PIG-LIVER ESTERASE AND PORCINE PANCREATIC LIPASE CATALYZED HYDROLYSES OF 3,4-(ISOPROPYLIDENEDIOXY)-2,5-TETRAHYDROFURANYL DIESTERS

被引：42

作者：

HULTIN, PG ^{[1
]}

MUESELER, FJ ^{[1
]}

JONES, JB ^{[1
]}

机构：

[1] UNIV TORONTO, DEPT CHEM, 80 ST GEORGE ST, TORONTO M5S 1A1, ONTARIO, CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 18期

关键词：

D O I：

10.1021/jo00018a033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pig liver esterase (PLE) and porcine pancreatic lipase (PPL) catalyzed hydrolyses of 2,5-bis(methoxycarbonyl) and 2,5-bis(acetoxymethyl) meso-diester derivatives of 3,4-(isopropylidenedioxy) tetrahydrofuran proceed with enantiotopic selectivity to give monoester products of up to 72% ee. Transesterification of the 2,5-bis(hydroxymethyl) derivative with trifluorethyl laurate promoted by PPL in ether also proceeds stereoselectively but in the opposite stereochemical sense from the hydrolysis of the corresponding diacetate. The data provide further examples of heteroatom and ester moiety induced reversals of stereoselectivity for the two enzymes.

引用

页码：5375 / 5380

页数：6

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