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A Linear Synthesis of Branched High‐Mannose Oligosaccharides from the HIV‐1 Viral Surface Envelope Glycoprotein gp120
Author(s) -
Ratner Daniel M.,
Plante Obadiah J.,
Seeberger Peter H.
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200203)2002:5<826::aid-ejoc826>3.0.co;2-2
Subject(s) - chemistry , glycoprotein , mannose , oligosaccharide , trisaccharide , glycoside , viral envelope , stereochemistry , glycosylation , monosaccharide , biochemistry
Described is a linear solution‐phase synthesis of the HIV‐1 viral surface envelope glycoprotein gp120 high‐mannose nonasaccharide pentyl glycoside. Envisioning the automated solid‐phase assembly of complex carbohydrates, the synthesis of the nonasaccharide and the related tri‐ and hexamannosides demonstrates the facile assembly of highly branched structures in a stepwise fashion incorporating monosaccharide building blocks. A differentially protected core trisaccharide was prepared and further elongated in two high‐yielding tri‐mannosylations to furnish the triantennary structure. The tri‐, hexa‐, and nonamannoside n ‐pentyl glycosides obtained via the described synthesis are currently being used for detailed study of the carbohydrate protein interactions responsible for binding of the anti‐HIV protein cyanovirin‐ N to the glycoprotein gp120. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)