Synthesis of allyl 2-O-(alpha-L-arabinofuranosyl)-6-O-(alpha-D-mannopyranosyl)-beta-D-mannopyranoside, a unique plant N-glycan motif containing arabinose.
The synthesis of the trisaccharide allyl 2-O-(alpha-L-arabinofuranosyl)-6-O-(alpha-D-mannopyranosyl)-beta-D-mannopyra-noside is reported. Stereoselective glycosylation at C-6 of a non-protected allyl beta-mannoside with the acetylated alpha-D-mannosyl bromide gave the alpha-(1 --> 6)-disaccharide as the main product and the crystalline 3,6-branched trisaccharide as minor compound. Further glycosylation of the 2,3 diol (1 --> 6) disaccharide with L-arabinofuranosyl bromide furnished a mixture of 3-O- and 2-O-alpha-L-Ara-trisaccharides from which the title compound was isolated.
Utille
J P
JP
Centre de Recherches sur les Macromolécules Végétales, UPR CNRS 5301 associated with the University Joseph Fourier, Grenoble, France. utille@cermav.cnrs.fr
Priem
B
B
D001089:Arabinose / Q000737:chemistry*; D002240:Carbohydrate Sequence; D006031:Glycosylation; D018551:Solanum lycopersicum / Q000737:chemistry; D008279:Magnetic Resonance Imaging; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D010944:Plants / Q000737:chemistry*; D011134:Polysaccharides / Q000737:chemistry*; D013237:Stereoisomerism
D009844:Oligosaccharides; D011134:Polysaccharides; C421466:allyl 2-O-arabinofuranosyl-6-O-mannopyranosylmannopyranoside; D001089:Arabinose