79365-98-3Relevant articles and documents
Heterologous over-expression of α-1,6-fucosyltransferase from Rhizobium sp.: Application to the synthesis of the trisaccharide β-D-GlcNAc(1 → 4)-[α-L-Fuc-(1 → 6)]-D-GlcNAc, study of the acceptor specificity and evaluation of polyhydroxylated indolizidines as inhibitors
Bastida, Agatha,Fernandez-Mayoralas, Alfonso,Gomez Arrayas, Ramon,Iradier, Fatima,Carretero, Juan Carlos,Garcia-Junceda, Eduardo
, p. 2390 - 2397 (2007/10/03)
An efficient heterologous expression system for overproduction of the enzyme α-1,6-Fucosyltransferase (α-1,6-FucT) from Rhizobium sp. has been developed. The gene codifying for the α-1,6-FucT was amplified by PCR using specific primers. After purification, the gene was cloned in the plasmid pKK223-3. The resulting plasmid, pKK1,6FucT, was transformed into the E. coli strain XL1-Blue MRF′. The protein was expressed both as inclusion bodies and in soluble form. Changing the induction time a five-fold increase of enzyme expressed in soluble form was obtained. In this way five units of enzyme α-1,6-FucT can be obtained per liter of culture. A crude preparation of the recombinant enzyme was used for the synthesis of the branched trisaccharide α-D-GlcNAc-(1 → 4)-[α-L-Fuc-(1 → 6)]-D-GlcNAc (3), from chitobiose (2) and GDP-Fucose (1). After purification, the trisaccharide 3 was obtained in a 84% overall yield. In order to elucidate the structural requirements for the acceptors, the specificity of the enzyme was studied towards mono-, di- and trisaccharides, which are structurally related to chitobiose. The enzyme uses, among others, the disaccharide N-acetyl lactosamine as a good substrate; the monosaccharide GlcNAc is a weak acceptor. Finally, several racemic polyhydroxylated indolizidines have been tested as potential inhibitors of the enzyme. Indolizidine 21 was the best inhibitor with an IC50 of 4.5 × 10-5M. Interestingly, this compound turned out to be the best mimic for the structural features of the fucose moiety in the presumed transition state. WILEY-VCH Verlag GmbH, 2001.
SYNTHESIS OF 2-ACETAMIDO-4-O-(2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL)-2-DEOXY-6-O-(α-L-FUCOPYRANOSYL)-D-GLUCOPYRANOSE (6-O-α-L-FUCOPYRANOSYL-DI-N-ACETYLCHITOBIOSE)
Oguri, Shigeyuki,Tejima, Setsuzo
, p. 1629 - 1635 (2007/10/02)
Benzyl 3,3',4',6'-tetra-O-benzoyl-β-di-N-acetylchitobioside (8) was prepared in 5 steps from 3,3',4',6'-tetra-O-acetyl-1,6-anhydro-β-di-N-acetylchitobiose by the following series of reactions; de-O-acetylation, benzoylation, acetolysis of the 1,6-anhydro-β-ring, benzyl glycosidation via oxazoline, and selective de-O-acetylation.Reaction of 8 with 2,3,4-tri-O-benzyl-α-L-fucopyranosyl bromide by a bromide ion-catalyzed reaction afforded benzyl 3,3',4',6'-tetra-O-benzoyl-6-O-(2",3",4"-tri-O-benzyl-α-L-fucopyranosyl)-β-di-N-acetylchitobioside (10) in 83.4 percent yield.After removal of the protecting groups of 10,6-O-α-L-fucopyranosyl-di-N-acetyl chitobiose (11) was obtained as needles. (13)C-NMR spectra data for 11 are presented.Keywords: - synthesis; 6-O-α-L-fucopyranosyl-di-N-acetylchitobiose; 1,6-anhydro-di-N-acetylchitobiose derivative; oxazoline glycosidation method; benzyl di-N-acetyl-chitobioside derivative; bromide ion-catalyzed glycosidation; selective de-O-acetylation; (13)C-NMR
