title: Highly productive autocondensation and transglycosylation reactions with Sulfolobus solfataricus glycosynthase.
abstract: 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.
authors: Istituto di Chimica Biomolecolare-Consiglio Nazionale delle Ricerche, Via Campi Flegrei 34, 80072 Pozzuoli, Naples, Italy. antonio.trincone@icb.cnr.it
authors: Antonio
authors: A
authors: Trincone
authors: Assunta
authors: A
authors: Giordano
authors: Giuseppe
authors: G
authors: Perugino
authors: Mosè
authors: M
authors: Rossi
authors: Marco
authors: M
authors: Moracci
mesh_terms: 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
chemical_list: D005960:Glucosides; D009838:Oligodeoxyribonucleotides; D014312:Trisaccharides; C025193:4-nitrophenyl beta-D-glucoside; C018616:2-nitrophenyl-beta-D-glucopyranoside; D005964:Glucosyltransferases