Glycosyl Azides – An Alternative Way to disaccharides

Bojarová, Pavla, Petrásková, Lucie, Ferrandi, Erica Elisa, Monti, Daniela, Pelantova, Helena, Kuzma, Mareka, Simerská, Pavla and Křen, Vladimir (2007) Glycosyl Azides – An Alternative Way to disaccharides. Advanced Synthesis & Catalysis, 349 8+9: 1514-1520. doi:10.1002/adsc.200700028


Author Bojarová, Pavla
Petrásková, Lucie
Ferrandi, Erica Elisa
Monti, Daniela
Pelantova, Helena
Kuzma, Mareka
Simerská, Pavla
Křen, Vladimir
Title Glycosyl Azides – An Alternative Way to disaccharides
Journal name Advanced Synthesis & Catalysis   Check publisher's open access policy
ISSN 1615-4150
Publication date 2007
Sub-type Article (original research)
DOI 10.1002/adsc.200700028
Volume 349
Issue 8+9
Start page 1514
End page 1520
Total pages 7
Place of publication Germany
Publisher Wiley - V C H Verlag GmbH & Co. KGaA
Language eng
Formatted abstract
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.
Keyword Azides
Enzyme catalysis
Glycosylation
Modified substrate
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: School of Chemistry and Molecular Biosciences
 
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Citation counts: TR Web of Science Citation Count  Cited 16 times in Thomson Reuters Web of Science Article | Citations
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Created: Tue, 27 Sep 2011, 16:24:30 EST by Dr Pavla Simerska on behalf of School of Chemistry & Molecular Biosciences