An Efficient Microwave-Mediated Synthesis of Hexavalent Sialic Acid Sulfoglycodendrimers as Potential Anti-HIV Agents
Publication Date
11-13-2020
Document Type
Article
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
Department
Chemistry
Recommended Citation
Cory Vierra, Daryl K. Eggers, Celia C. Labranche, and Katherine D. McReynolds. "An Efficient Microwave-Mediated Synthesis of Hexavalent Sialic Acid Sulfoglycodendrimers as Potential Anti-HIV Agents" ACS Applied Polymer Materials (2020): 4345-4351. https://doi.org/10.1021/acsapm.0c00538
