Synthesis of a hexasaccharide acceptor corresponding to the reducing terminus of mycobacterial 3-O-methylmannose polysaccharide (MMP).
The title compound methyl O-(2,6-di-O-benzyl-3-O-methyl-alpha-D-mannopyranosyl)-[(1-->4) -O-(2,6-di-O-benzyl-3-O-methyl-alpha-D-mannopyranosyl)]4-(1-->4) -2,6-di-O-benzyl-3-O-methyl-alpha-D-mannopyranoside (2) was synthesized in a blockwise manner, employing trichloroacetimidate (11) and (20) as glycosyl donors. The strategy relies on the single-step preparation of the 3-O-methyl ethers (4) and (12) as starting materials. Since all intermediates contain one or more OCH3 groups, they are easily identified by NMR spectroscopy using the methyl proton signals. Compound 2 corresponds to the reducing terminal hexasaccharide of mycobacterial 3-O-methyl-mannose polysaccharide (MNP). MMP has the unusual property of stimulating the fatty acid synthetase multienzyme complex. Compound 2 can serve as a suitable glycosyl acceptor for the synthesis of extended fragments of MMP.
Liao
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Research Center for Eco-Environmental Sciences, Academia Sinica, Beijing, PR China.
Lu
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D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D009682:Magnetic Resonance Spectroscopy; D008766:Methylmannosides / Q000737:chemistry*; D008969:Molecular Sequence Data; D009161:Mycobacterium / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis*; D012091:Repetitive Sequences, Nucleic Acid
D008766:Methylmannosides; D009844:Oligosaccharides; C043123:3-O-methylmannose