Enantioselective Stereoinversion in the Kinetic Resolution of rac-sec-Alkyl Sulfate Esters by Hydrolysis with an Alkylsulfatase from Rhodococcus ruber DSM 44541 Furnishes Homochiral Products

The biocatalytic hydrolysis of (±)‐sec‐alkyl sulfate esters with an alkylsulfatase from Rhodococcus ruber DSM 44541 proceeded with high enantioselectivity (up to 99 % ee) and with absolute stereoselectivity through inversion of configuration. Thus, a rac substrate was converted into homochiral S‐con...

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Bibliographic Details
Published in:	Angewandte Chemie International Edition Vol. 41; no. 21; pp. 4052 - 4054
Main Authors:	Pogorevc, Mateja, Kroutil, Wolfgang, Wallner, Sabine R., Faber, Kurt
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 04-11-2002 WILEY‐VCH Verlag
Subjects:	alkylsulfatase biotransformations configuration inversion Esters - chemistry Esters - metabolism Hydrolysis Kinetics Molecular Conformation Rhodococcus - enzymology Stereoisomerism Sulfatases - metabolism sulfate ester Sulfates - chemistry Sulfates - metabolism
Online Access:	Get full text
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Summary:	The biocatalytic hydrolysis of (±)‐sec‐alkyl sulfate esters with an alkylsulfatase from Rhodococcus ruber DSM 44541 proceeded with high enantioselectivity (up to 99 % ee) and with absolute stereoselectivity through inversion of configuration. Thus, a rac substrate was converted into homochiral S‐configured products (see scheme).
Bibliography:	ArticleID:ANIE4052 istex:276A7F9DB975079D10B35C777CAEA971BE2AA492 ark:/67375/WNG-BVMKLM8K-P We thank Degussa AG (Frankfurt) for financial support and T. Riermeier and H. Trauthwein for their valuable contributions. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1433-7851 1521-3773
DOI:	10.1002/1521-3773(20021104)41:21<4052::AID-ANIE4052>3.0.CO;2-W