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Enzymatic synthesis of metronidazole esters and their monosaccharide ester derivatives

Paper ID Volume ID Publish Year Pages File Format Full-Text
18346 42719 2006 6 PDF Available
Title
Enzymatic synthesis of metronidazole esters and their monosaccharide ester derivatives
Abstract

An efficient enzymatic method for preparation of lipophilic metronidazole ester bearing with a long chain acyl group and hydrophilic metronidazole-saccharide derivatives was developed in the paper. Transesterification reactions of metronidazole with fatty acid vinyl esters (from vinyl caprylate to vinyl stearate) and divinyl dicarboxylate (from divinyl butanedioate to divinyl decanedioate) in anhydrous tetrahydrofuran were catalyzed by Candida antarctica lipase acrylic resin and provided a series of lipophilic metronidazole ester. Subsequently, under the catalysis of alkaline protease from Bacillus subtilis, acylation of d-glucose and d-mannose with metronidazole vinyl ester was carried out in pyridine. Hydrophilic metronidazole-saccharide derivatives were regioselectivly synthesized. Reaction conditions including enzyme sources and solvents for the esterification of metronidazole were examined in detail. The result of enzyme screening showed that C. antarctica lipase acrylic resin in tetrahydrofuran exhibited the highest catalytic activity and the conversion ratio of metronidazole after 24 h was up to 97.4%. Polarity and substrate solubility of reaction solvents have great influence on the enzymatic transesterification. Polar solvents in which metronidazole has high solubility are favorable.

Keywords
Enzymatic transesterification; Metronidazole; Esters; Monosaccharide
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Enzymatic synthesis of metronidazole esters and their monosaccharide ester derivatives
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Publisher
Database: Elsevier - ScienceDirect
Journal: Enzyme and Microbial Technology - Volume 39, Issue 6, 3 October 2006, Pages 1258–1263
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us