Synthesis of a polymerizable, bivalent glycan mimetic of the HIV envelope spike gp120

TETRAHEDRON LETTERS

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Article

Sletten, Eric T.¹  Svec, Riley L.¹  Nguyen, Hien M.¹ 

[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA

关键词: HIV;    Glycopolymer;    Carbohydrate synthesis;    Nickel catalyzed;   

DOI  :  10.1016/j.tetlet.2015.01.016

来源: Elsevier

【 摘 要 】

A synthetic study on the creation of a bivalent, ROMP capable monomer has the ability to be polymerized into the corresponding neo-glycopolymer mimetic of the surface glycans on gp120 envelope spike of the HIV virus. In our approach, we have developed a new strategy for orthogonally attaching both the terminal Manot(1-2)Man disaccharide unit of the D1 arm of Man(9)GlcNAc(2) of HIV gp120 and the terminal Man alpha 1-2 unit of its D2 arm to a bivalent scaffold to produce the corresponding polymerizable monomer. The Man alpha 1-2 saccharide moieties were assembled using a nickel catalyst, Ni(4-F-PhCN)(4)(OTf)(2), to activate trihaloacetimidate donors under a mild and operationally simple procedure. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

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