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Synthesis of a hexasaccharide fragment of the 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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b-D D -Xylp-(1 fi 4)-a-D D -Manp-(1 fi 3)-[b-D D -Xylp-(1 fi 2)]-a-D D -Manp-(1 fi 3)-[b-D D -Xylp-(1 fi 2)]-a-D D -Manp, the fragment of the exopolysaccharide from Cryptococcus neoformans serovar B, was synthesized as its methyl glycoside. Thus, acetylation of allyl 3-O-benzoyl-4,6-O-benzylidene-a-D D -mannopyranoside (1) followed by debenzylidenation and selective 6-O-benzoylation afforded allyl 2-O-acetyl-3,6-di-O-benzoyl-a-D D -mannopyranoside (4). Glycosylation of 4 with 2,3,4-tri-O-benzoyl-D D -xylopyranosyl trichloroacetimidate (5) furnished the b-(1 fi 4)-linked disaccharide 6. Deallylation followed by trichloroacetimidate formation gave the disaccharide donor 8, and subsequent coupling with allyl 2,3,4-tri-O-benzoyl-b-D D -xylopyranosyl-(1 fi 2)-4,6-di-O-benzoyl-a-D Dmannopyranoside (9), produced the tetrasaccharide 10. Reiteration of deallylation and trichloroacetimidate formation from 10 yielded the tetrasaccharide donor 12. The downstream disaccharide acceptor 18 was obtained by condensation of 5 with methyl 3-Oacetyl-4,6-O-benzylidene-a-D D -mannopyranoside, followed by debenzylidenation, benzoylation, and selective 3-O-deacetylation. Coupling of 18 with 12 afforded th

Who reads Synthesis of a hexasaccharide fragment of the O-deacetylated GXM of C. neoformans serotype B?

Author

Wei Zhao; Fanzuo Kong

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

2004

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)