Glycosyl Azides – An Alternative Way to Disaccharides

Advanced Synthesis and Catalysis - Tập 349 Số 8-9 - Trang 1514-1520 - 2007
Pavla Bojarová1,2, Lucie Petrásková3, Erica Elisa Ferrandi4, Daniela Monti4, Helena Pelantová3, Marek Kuzma3, Pavla Simerská3, Vladimı́r Křen3
1Department of Biochemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 12840 Praha 2, Czech Republic
2Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, 142 20 Praha 4, Czech Republic, Fax: (+420)‐296‐442‐509
3Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, 142 20 Praha 4, Czech Republic, Fax: (+420)-296-442-509
4Istituto di Chimica del Riconoscimento Molecolare, CNR, Via Mario Bianco 9, 20131, Milano, Italy

Tóm tắt

AbstractGlycosyl 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.

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Thông tin xuất bản

Advanced Synthesis and Catalysis

Tập 349 Số 8-9

1514-1520

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