Synthesis of L-trehalose and observations on isomer and by-product formation.
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.
Haines
Alan H
AH
Centre for Carbohydrate Chemistry, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, UK. a.haines@uea.ac.uk
D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D014199:Trehalose / Q000138:chemical synthesis* / Q000737:chemistry*
D014199:Trehalose