Comparison of different strategies for the lipase-catalyzed preparative resolution of racemic acids and alcohols: Asymmetric hydrolysis, esterification, and transesterification.

Comparison of different strategies for the lipase-catalyzed preparative resolution of racemic acids and alcohols: Asymmetric hydrolysis, esterification, and transesterification. Research Abstract Details 

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Comparison of different strategies for the lipase-catalyzed preparative resolution of racemic acids and alcohols: Asymmetric hydrolysis, esterification, and transesterification. Abstract Text:

Lipase from Candida cylindracea has been found to be a highly stereospecific catalyst suitable for preparative resolution of racemic acids and alcohols. Using (R, S)-2-(p-chlorophenoxy) propionic acid (whose R isomer is a herbicide) and (R, S)-sec-butanol (a versatile synthon) as model compounds, three alternative approaches to lipase-catalyzed resolutions-asymmetric hydrolysis, esterification, and transesterification-have been compared. Enzymatic esterification in biphasic systems has been ruled out for preparative resolutions because addition of the acids lowers the pH of the aqueous phase thereby greatly reducing the efficiency of the procedure. Both enzymatic hydrolysis and biphasic transesterification afforded resolution of the racemates on a gram scale. From the standpoint of productivity, ease of product separation, and the amount of steps required, lipasecatalyzed asymmetric hydrolysis has been judged to be superior for the practical resolution of racemic acids, and lipase-catalyzed asymmetric transesterification to be the method of choice for the practical resolution of racemic alcohols.

Comparison of different strategies for the lipase-catalyzed preparative resolution of racemic acids and alcohols: Asymmetric hydrolysis, esterification, and transesterification. Publishing Authors By Initials

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Comparison of different strategies for the lipase-catalyzed preparative resolution of racemic acids and alcohols: Asymmetric hydrolysis, esterification, and transesterification. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Biotechnology and bioengineering

VOLUME: 26

Page Numbers: 1449-54

Journal Abbreviation: Biotechnol. Bioeng.

ISSN: 0006-3592

DAY: 13

MONTH: Dec

YEAR: 1984

Comparison of different strategies for the lipase-catalyzed preparative resolution of racemic acids and alcohols: Asymmetric hydrolysis, esterification, and transesterification. Information

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LANGUAGE: eng

NlmUniqueID: 7502021

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Grant and Affiliation Information for Comparison of different strategies for the lipase-catalyzed preparative resolution of racemic acids and alcohols: Asymmetric hydrolysis, esterification, and transesterification.

AFFILIATION: Laboratory of Applied Biochemistry, Department of Nutrition and Food Science, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139.

Country: United States

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MEDLINETA: Biotechnol Bioeng

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