Enzymatic synthesis of oligo-D-galactofuranosides and l-arabinofuranosides: from molecular dynamics to immunological assays

0349850 - ÚMG 2011 RIV GB eng J - Journal Article
Chlubnová, I. - Filipp, Dominik - Spiwok, V. - Dvořáková, H. - Daniellou, R. - Nugier-Chauvin, C. - Králová, B. - Ferrieres, V.
Enzymatic synthesis of oligo-D-galactofuranosides and l-arabinofuranosides: from molecular dynamics to immunological assays.
Organic & Biomolecular Chemistry. Roč. 7, 8-9 (2010), s. 2092-2102. ISSN 1477-0520. E-ISSN 1477-0539
Institutional research plan: CEZ:AV0Z50520514
Keywords : enzymatic synthesis * oligofuranosides * immune stimulation
Subject RIV: EB - Genetics ; Molecular Biology
Impact factor: 3.451, year: 2010

D-Galactofuranosyl-containing conjugates are ubiquitous in many pathogenic microorganisms, but completely absent from mammals. Based on the similarity between chemical structures, the arabinofuranosyl hydrolase Araf51 from Clostridium thermocellum was not only able to hydrolyze galactosyl derivatives, but was also really efficient in catalyzing oligomerisations using p-nitrophenyl furanosides as donors. The structures of the products obtained were determined using MS and NMR approaches. Amongst them, all the possible regioisomers of di-arabino and -galactofuranosides were synthesized. The galactofuranobioside displaying the biologically relevant sequence beta-D-Galf-(1,6)-beta-D-Galf was enzymatically prepared for the first time. All fractions going from di- to penta-arabino- and galactofuranosides were tested for their ability in eliciting the production of TNF-alpha. Interesting immunological properties were observed with arabinofuranosides as short as three sugar residues.
Permanent Link: http://hdl.handle.net/11104/0189985