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Enzymatic synthesis of 4-methylumbelliferyl (1 -> 3)-beta-D-glucooligosaccharides - new substrates for beta-1,3-1,4-D-glucanase

TitleEnzymatic synthesis of 4-methylumbelliferyl (1 -> 3)-beta-D-glucooligosaccharides - new substrates for beta-1,3-1,4-D-glucanase
Publication TypeJournal Article
Year of Publication2003
AuthorsBorriss, R, Krah, M, Brumer, H, Kerzhner, MA, Ivanen, DR, Eneyskaya, EV, Elyakova, LA, Shishlyannikov, SM, Shabalin, KA, Neustroev, KN
JournalCARBOHYDRATE RESEARCH
Volume338
Pagination1455-1467
Date PublishedJUL 4
Type of ArticleArticle
ISSN0008-6215
Abstract

The transglycosylation reactions catalyzed by beta-1,3-D-glucanases (laminaranases) were used to synthesize a number of 4-methylumbelliferyl (MeUmb) (1 –> 3)-beta-D-gluco-oligosaccharides having the common structure {[}beta-D-Glcp-(1 –> 3)](n)-beta-D-Glcp-MeUmb, where n = 1-5. The beta-1,3-D-glucanases used were purified from the culture liquid of Oerskovia sp. and from a homogenate of the marine mollusc Spisula sachalinensis. Laminaran and curdlan were used as (1 –> 3)-beta-D-glucan donor substrates, while MeUmb-beta-D-glucoside (MeUmbGlcp) was employed as a transglycosylation acceptor. Modification of {[}beta-D-Glcp-(1 –> 3)](2)-beta-D-Glcp-MeUmb (MeUmbG(3)) gives 4,6-O-benzylidene-D-glucopyranosyl or 4,6-O-ethylidene-D-glucopyranosyl groups at the non-reducing end of artificial oligosaccharides. The structures of all oligosaccharides obtained were solved by H-1 and C-13 NMR spectroscopy and electrospray tandem mass spectrometry. The synthetic oligosaccharides were shown to be substrates for a beta-1,3-1,4-D-glucanase from Rhodothermus marinus, which releases MeUmb from beta-di- and beta-triglucosides and from acetal-protected beta-triglucosides. When acting upon substrates with d.p. > 3, the enzyme exhibits an endolytic activity, primarily cleaving off MeUrnbGlcP and MeUmbG(2). (C) 2003 Elsevier Science Ltd. All rights reserved.

DOI10.1016/S0008-6215(03)00199-X