Highly productive autocondensation and transglycosylation reactions with Sulfolobus solfataricus glycosynthase.
Transglycosylation reactions (autocondensation of the substrate or transfer of the glycon donor moiety to different acceptors) with the hyperthermophilic glycosynthase from Sulfolobus solfataricus acting in dilute sodium formate buffer at pH 4.0 are reported; the use of 4-nitrophenyl beta-glucopyranoside as both donor and acceptor in the self-transfer reaction and a highly productive reaction with 1.1 M 2-nitrophenyl beta-glucopyranoside were possible. Interesting effects, governed by the anomeric configuration and lipophilicity of heteroacceptors, on the regioselectivity and yield of reactions were found for the first time with this enzyme and are discussed. The results demonstrate the unexplored synthetic potential of this glycosynthase; the tuning of the reaction conditions and the choice of different donors/acceptors can lead to products of applicative interest.
Trincone
Antonio
A
Istituto di Chimica Biomolecolare-Consiglio Nazionale delle Ricerche, Via Campi Flegrei 34, 80072 Pozzuoli, Naples, Italy. antonio.trincone@icb.cnr.it
Giordano
Assunta
A
Perugino
Giuseppe
G
Rossi
Mosè
M
Moracci
Marco
M
D004579:Electron Transport; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D005964:Glucosyltransferases / Q000737:chemistry* / Q000378:metabolism; D006031:Glycosylation; D007700:Kinetics; D009838:Oligodeoxyribonucleotides / Q000737:chemistry; D013329:Structure-Activity Relationship; D013379:Substrate Specificity; D048229:Sulfolobus solfataricus / Q000201:enzymology*; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D005960:Glucosides; D009838:Oligodeoxyribonucleotides; D014312:Trisaccharides; C025193:4-nitrophenyl beta-D-glucoside; C018616:2-nitrophenyl-beta-D-glucopyranoside; D005964:Glucosyltransferases