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Glycosyl Azides – An Alternative Way to Disaccharides
Author(s) -
Bojarová Pavla,
Petrásková Lucie,
Ferrandi Erica Elisa,
Monti Daniela,
Pelantová Helena,
Kuzma Marek,
Simerská Pavla,
Křen Vladimír
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700028
Subject(s) - glycosyl , chemistry , azide , regioselectivity , glycosylation , glycosyl donor , glycoside , carbohydrate synthesis , glycoside hydrolase , combinatorial chemistry , stereochemistry , organic chemistry , carbohydrate , hydrolysis , catalysis , biochemistry
Glycosyl azides are shown to be efficient donors for β‐galactosidases, β‐glucosidases and α‐mannosidases. Only α‐galactosidases do not cleave the respective glycosyl azide 1 and, moreover, they exhibit competitive inhibition (especially α‐galactosidase from Talaromyces flavus ). High water solubility and ready synthesis of glycosyl azides enable transglycosylation reactions even with difficult acceptors like N ‐acetyl‐ D ‐mannosamine in good yields. The versatility of glycosyl azides was demonstrated in the synthesis of five disaccharides – two of them are described for the first time. All the reactions were highly regioselective, yielding β(1→6) isomers. β‐Galactosidase from E. coli proved to have the best synthetic capabilities. The present study shows that glycosyl azides are a valuable alternative to common p ‐nitrophenyl glycoside donors and in many synthetic reactions.