Synthesis of L-trehalose and observations on isomer and by-product formation |
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Authors: | Haines Alan H |
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Institution: | Centre for Carbohydrate Chemistry, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, UK. a.haines@uea.ac.uk |
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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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Keywords: | L-Trehalose Anhydrobiosis Biostabilisation 1 1′-Linked disaccharide |
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