Synthesis of L-trehalose and observations on isomer and by-product formation

Haines, Alan H. (2003) Synthesis of L-trehalose and observations on isomer and by-product formation. Carbohydrate Research, 338 (9). pp. 813-818. ISSN 0008-6215

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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 α,α-, α,β-, β,β-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 α- and β-L-glucopyranoside are by-products in the trimethylsilyl trifluoromethanesulphonate mediated formation of the 1,1′-linked disaccharides.

Item Type: Article
Uncontrolled Keywords: 1,1′-linked disaccharide,anhydrobiosis,biostabilisation,l-trehalose,analytical chemistry,biochemistry,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1602
Faculty \ School: Faculty of Science > School of Chemistry
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Depositing User: LivePure Connector
Date Deposited: 14 Jul 2022 12:30
Last Modified: 23 Oct 2022 03:52
DOI: 10.1016/S0008-6215(03)00043-0

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