Title

An Efficient Microwave-Mediated Synthesis of Hexavalent Sialic Acid Sulfoglycodendrimers as Potential Anti-HIV Agents

Publication Date

11-13-2020

Document Type

Article

Department

Chemistry

Publication Title

ACS Applied Polymer Materials

Volume

2

Issue

11

DOI

10.1021/acsapm.0c00538

First Page

4345

Last Page

4351

Abstract

A series of four sialic acid-containing hexavalent sulfoglycodendrimers (SGDs) were synthesized in excellent yields using an efficient strategy involving multiple microwave-mediated reactions. Four sugars, sialic acid, and the dimer through tetramer of α-2→8-linked oligosialic acid were added to an aminooxy-terminated hexavalent dendrimer core using a chemoselective oxime-forming reaction. This method resulted in substantial improvements in reaction time and product yield compared with previous methods. These multivalent glycopolymers were designed as potential topical agents for prevention of sexual transmission of HIV-1. While inactive against HIV-1, the SGDs were also not cytotoxic, opening a pathway for the further development of anti-HIV SGDs.

Funding Number

HHSN272201800004C

Funding Sponsor

National Science Foundation

Keywords

aminooxy, glycodendrimers, HIV-1, microscale thermophoresis, microwave synthesis, oligosialic acid, oxime, sialic acid

Share

COinS