Synthesis of the tetrasaccharide core region of antigenic lipo-oligosaccharides characteristic of Mycobacterium kansasii.
The oligosaccharide core region, beta-D-Glcp-(1----3)-beta-D-Glcp-(1----4)-alpha-D-Glcp- 1----1)-alpha-D-Glcp (1), of the lipo-oligosaccharide-type antigens isolated from M. kansasii has been synthesised from 2,3,2',3',4',6'-hexa-O-benzyl-6-O-(1-phenylethyl)-alpha, alpha-trehalose (4). Compound 4 was obtained by LiAlH4-AlCl3-type hydrogenolysis of 2,3,2',3',4',6'-hexa-O-benzyl-4,6-O-(S)-(1-phenylethylidene)-alpha , alpha-trehalose. The beta-laminaribiosyl part of the molecule was built-up by sequential glycosylation steps using 2,4,6-tri-O-acetyl-3-O-allyl-alpha-D-glucopyranosyl bromide in the presence of HgBr2 and methyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranoside promoted by methyl triflate. The complete a priori 13C-n.m.r. spectrum assignment of 1 was achieved by applying 2D methods.
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Institute of Biochemistry, L. Kossuth University, Debrecen, Hungary.
Kerékgyártó
J
J
Szurmai
Z
Z
Duddeck
H
H
D007202:Indicators and Reagents; D008070:Lipopolysaccharides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D009161:Mycobacterium / Q000276:immunology*; D009844:Oligosaccharides / Q000138:chemical synthesis*; D009904:Optical Rotation
D007202:Indicators and Reagents; D008070:Lipopolysaccharides; D009844:Oligosaccharides; C023023:lipid-linked oligosaccharides