期刊
GLYCOBIOLOGY
卷 21, 期 4, 页码 448-456出版社
OXFORD UNIV PRESS INC
DOI: 10.1093/glycob/cwq177
关键词
alpha-galacto-oligosaccharides; glycosynthase; alpha-gal epitope; carbohydrate synthesis; protein engineering
资金
- Agenzia Spaziale Italiana [1/014/06/0]
- US National Science Foundation
The large-scale production of oligosaccharides is a daunting task, hampering the study of the role of glycans in vivo and the testing of the efficacy of novel glycan-based drugs. Glycosynthases, mutated glycosidases that synthesize oligosaccharides in high yields, are becoming important chemo-enzymatic tools for the production of oligosaccharides. However, while beta-glycosynthase can be produced with a rather well-established technology, examples of alpha-glycosynthases are thus far limited only to enzymes from glycoside hydrolase 29 (GH29), GH31 and GH95 families. alpha-l-Fucosynthases from GH29 use convenient glycosyl azide derivatives as a strategic alternative to glycosyl fluoride donors. However, the general applicability of this method to other alpha-glycosynthases is not trivial and remains to be confirmed. Here, beta-d-galactopyranosyl azide was converted to alpha-galacto-oligosaccharides with good yields and high regioselectivity, catalyzed by a novel alpha-galactosynthase based on the GH36 alpha-galactosidase from the hyperthermophilic bacterium Thermotoga maritima. These results open a new avenue to the practical synthesis of biologically interesting alpha-galacto-oligosaccharides and demonstrate more widespread use of beta-glycosyl-azide as donors, confirming their utility to expand the repertoire of glycosynthases.
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