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  • Title: [Synthesis of p-nitrophenyl laminarioligosides via transglycosylation reaction catalyzed by endo-1,3-beta-D- glucanase from marine mollusk].
    Author: Zviagintseva TN, Makar'eva TN, Ermakova SP, Eliakova LA.
    Journal: Bioorg Khim; 1998 Mar; 24(3):219-23. PubMed ID: 9612564.
    Abstract:
    The transglycosylation reaction catalyzed by endo-1,3-beta-D-glucanase LIV from the marine mollusk Spisula sachalinensis was studied with the goal of preparing p-nitrophenyl (Np) 1,3- and 1,3; 1,6-D-glucooligosides. As donors we used the 1,3;1,6-beta-D-glucans with various content of beta-1, 6-glucoside bonds: laminarians [from Laminaria cichorioides (10%), L. gurjanovae (2%), and Fucus evanescens (35%)] and translam (25%); as acceptor we used the p-nitrophenyl beta-D-glucoside (GNp). The maximal yield of the transglycosylation products was found when using laminaran from Laminaria cichorioides; donors with a lower or higher content of beta-1,6-glucoside bonds were less efficient. The laminaran from F. evanescens and translam gave no Np-laminaribioside. At optimal conditions (10 mg/ml of laminaran from L. cichorioides and 5 mg/ml of GNp), maximal yields of Np-laminaribioside, Np-trioside, Np-tetraoside, and Np-pentaoside were 19, 8, 3, and 1%, respectively. The first two compounds were isolated by chromatography on silica gel, their physicochemical characteristics were obtained, and their structures were established by 13C NMR spectroscopy.
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