1357933-65-3Relevant academic research and scientific papers
A novel, efficient and sustainable strategy for the synthesis of α-glycoconjugates by combination of a α-galactosynthase and a green solvent
Bayón,Moracci,Hernáiz
, p. 55313 - 55320 (2015)
Glycosynthases are becoming important enzymatic tools for the synthesis of oligosaccharides. Herein, we explore for the first time the synthesis of α-glycoconjugates using a α-glycosynthase in green solvents. Using this biocatalyst, β-Gal-N3 as donor, pNP-Glc and pNP-Man as acceptors, and green co-solvents we obtained high yields and excellent selectivities in the synthesis of α-glycoconjugates. In addition, reaction scale-up is feasible and co-solvent can be recovered and reused, increasing the sustainability of the reaction process. The results demonstrate that the combination of a glycosynthase and a green solvent is a promising alternative for the synthesis of glycoconjugates. The non-hydrolytic capability of this enzyme on the product obtained is a key feature that can be expanded to other glycosynthases.
A novel -d-galactosynthase from Thermotoga maritima converts -d-galactopyranosyl azide to -galacto-oligosaccharides
Cobucci-Ponzano, Beatrice,Zorzetti, Carmela,Strazzulli, Andrea,Carillo, Sara,Bedini, Emiliano,Corsaro, Maria Michela,Comfort, Donald A.,Kelly, Robert M.,Rossi, Mos,Moracci, Marco
experimental part, p. 448 - 456 (2012/01/12)
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 β-glycosynthase can be produced with a rather well-established technology, examples of -glycosynthases are thus far limited only to enzymes from glycoside hydrolase 29 (GH29), GH31 and GH95 families. α-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 α-glycosynthases is not trivial and remains to be confirmed. Here, β-d-galactopyranosyl azide was converted to α-galacto- oligosaccharides with good yields and high regioselectivity, catalyzed by a novel -galactosynthase based on the GH36 α-galactosidase from the hyperthermophilic bacterium Thermotoga maritima. These results open a new avenue to the practical synthesis of biologically interesting α-galacto- oligosaccharides and demonstrate more widespread use of α-glycosylα- azide as donors, confirming their utility to expand the repertoire of glycosynthases.
