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Novel transglucosylating reaction of sucrose phosphorylase to carboxylic compounds such as benzoic acid

Paper ID Volume ID Publish Year Pages File Format Full-Text
22149 43257 2007 8 PDF Available
Title
Novel transglucosylating reaction of sucrose phosphorylase to carboxylic compounds such as benzoic acid
Abstract

We examined the synthesis of benzoyl glucoside using the transglucosylation reaction of sucrose phosphorylase. Sucrose phosphorylase from Streptococcus mutans showed marked transglucosylating activity, particularly under acidic conditions. On the other hand, sucrose phosphorylase from Leuconostoc mesenteroides showed very weak transglucosylating activity. Three main products were detected from the reaction mixture using benzoic acid as an acceptor molecule and sucrose as a donor molecule. These compounds were identified as 1-O-benzoyl α-D-glucopyranoside, 2-O-benzoyl α-D-glucopyranose and 2-O-benzoyl β-D-glucopyranose on the basis of their isolation and the isolation of their acetylated products and subsequent analysis using 1D- and 2D-NMR analyses. From the results of the time-course analyses of the enzyme reaction and the degradation of 1-O-benzoyl α-D-glucopyranoside, 1-O-benzoyl α-D-glucopyranoside was considered to be initially produced by the transglucosylation reaction of the enzyme, and 2-O-benzoyl α-D-glucopyranose and 2-O-benzoyl β-D-glucopyranose were produced from 1-O-benzoyl α-D-glucopyranoside by intramolecular acyl migration reaction. The acceptor specificity in the glucosylation reaction of S. mutans sucrose phosphorylase was also investigated. This sucrose phosphorylase could transglucosylate toward various carboxylic compounds. Short-chain fatty acids, hydroxy acids and dicarboxylic acids were also glucosylated with this sucrose phosphorylase.

Keywords
sucrose phosphorylase; transglucosylation; carboxylic group; carboxylic compounds; sucrose; benzoic acid; intramolecular acyl migration
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Novel transglucosylating reaction of sucrose phosphorylase to carboxylic compounds such as benzoic acid
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Bioscience and Bioengineering - Volume 104, Issue 1, July 2007, Pages 22–29
Authors
, , , , , , ,
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