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Updated: Sep 26, 2026

Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues
Published on: February 17, 2017
Synthesis of L-trehalose and observations on isomer and by-product formation
1Centre for Carbohydrate Chemistry, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, UK. a.haines@uea.ac.uk
Abstract:
With a view to gaining evidence on the mechanism by which D-trehalose is able to stabilise biomolecules towards dehydration (anhydrobiosis) and heat, L-trehalose has been prepared in order to allow comparative studies to be made. Little change can be induced in the ratio of the alpha,alpha-, alpha,beta-, beta,beta-1,1'-stereoisomers of the disaccharide formed from 2,3,4,6-tetra-O-benzyl-L-glucose by using different reaction procedures and by varying the reaction conditions. Benzyl 2,3,4,6-tetra-O-benzyl alpha- and beta-L-glucopyranoside are by-products in the trimethylsilyl trifluoromethanesulphonate mediated formation of the 1,1'-linked disaccharides.
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