Enzymatic synthesis of 4-methylumbelliferyl (1 -> 3)-beta-D-glucooligosaccharides - new substrates for beta-1,3-1,4-D-glucanase
2003 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 338, no 14, 1455-1467 p.Article in journal (Refereed) Published
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).
Place, publisher, year, edition, pages
2003. Vol. 338, no 14, 1455-1467 p.
4-methylumbelliferyl (1 -> 3)-beta-D-glucoside, beta-1,3-1,4-D-glucanase, Rhodothermus marinus, transglycosylation, laminaranase, rhodothermus-marinus, alpha, glycosides, kinetics, 4-glucanohydrolases, transglycosylation, oligosaccharides, glycosynthases, galactosidases, glycoproteins
IdentifiersURN: urn:nbn:se:kth:diva-22661DOI: 10.1016/s0008-6215(03)00199-xISI: 000184063400002OAI: oai:DiVA.org:kth-22661DiVA: diva2:341359
QC 201005252010-08-102010-08-10Bibliographically approved