[Synthesis of p-nitrophenyl laminarioligosides via transglycosylation reaction catalyzed by endo-1,3-beta-D- glucanase from marine mollusk].
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.
Zviagintseva
T N
TN
Pacific Institute of Bioorganic Chemistry, Far East Division, Russian Academy of Sciences, Vladivostok, Russia.
Makar'eva
T N
TN
Ermakova
S P
SP
Eliakova
L A
LA
D000818:Animals; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D004693:Glucan Endo-1,3-beta-D-Glucosidase / Q000737:chemistry*; D005936:Glucans / Q000737:chemistry; D006031:Glycosylation; D007795:Laminaria / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008974:Mollusca / Q000201:enzymology*; D009596:Nitrophenols / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis*; D011134:Polysaccharides / Q000737:chemistry; D013379:Substrate Specificity
D005936:Glucans; D009596:Nitrophenols; D009844:Oligosaccharides; D011134:Polysaccharides; C033671:epiglucan; C008247:laminaran; D004693:Glucan Endo-1,3-beta-D-Glucosidase; C024836:4-nitrophenol
Poluchenie p-nitrofenil-laminarioligozidov reaktsieĭ transglikozilirovaniia, kataliziruemoĭ éndo-1,3-beta-d-gliukanazoĭ iz morskogo molliuska.