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Facile synthesis of the heptasaccharide repeating unit of O-deacetylated GXM of C. neoformans serotype B by Wei Zhao; Fanzuo Kong is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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A heptasaccharide, b-D D-Xylp-(1!2)-a-D D-Manp-(1!3)-[b-D D-Xylp-(1!2)]-a-D D-Manp-(1!3)-[b-D D-GlcpA-(1!2)][b-D D-Xylp-(1!4)]-a-D D-Manp, the repeating unit of the exopolysaccharide from Cryptococcus neoformans serovar B, was synthesized as its methyl glycoside. Thus 2,3,4-tri-O-benzoyl-b-D D-xylopyranosyl-(1!2)-3,4,6-tri-O-benzoyl-a-D D-mannopyranosyl trichloroacetimidate (7) and allyl 2,3,4-tri-O-benzoyl-b-D D-xylopyranosyl-(1!2)-4,6-di-O-benzoyl-a-D D-mannopyranoside (8), readily obtained from the corresponding monosaccharide derivatives via simple transformation, were coupled to give a (1!3)-linked tetrasaccharide 9. Deallylation of 9 followed by trichloroacetimidate formation produced the tetrasaccharide donor 11. Condensation of methyl 2,3,4-tri-O-benzoyl-b-D D-xylopyranosyl-(1!4)-2-O-acetyl-6-O-benzoyl-a-D D-mannopyranoside (18) with 11 followed by selective deacetylation yielded hexasaccharide acceptor 20. Coupling of 20 with methyl 2,3,4-tri-O-acetyl-a-D D-glucopyranosyluronate bromide (21) and subsequent deprotection furnished the target heptaoside. A hexasaccharide fragment, a-D D-Manp-(1!3)-[b-D D-Xylp- (1!2)]-a-D D-Manp-(1!3)-[b-D D-GlcpA-(1!2)][b-D D-Xylp-(1!4)]-a-D

Who reads Facile synthesis of the heptasaccharide repeating unit of O-deacetylated GXM of C. neoformans serotype B?

Author

Wei Zhao; Fanzuo Kong

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0968-0896)

Published

2005

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)