ORGN 225 |
| To initiate an immune response, dendritic cells degrade microorganisms and display the resulting antigens to T-lymphocytes. Several transmembrane receptors are involved in these functions, including DC-SIGN. Certain pathogens, such as HIV-1, exploit interactions with DC-SIGN to avoid degradation and enhance their infectivity; therefore, DC-SIGN is an interesting target. It is a C-type lectin, a member of the class of Ca2+-dependent carbohydrate-binding proteins, and is known to bind mannosides. We are pursuing the synthesis and screening of a directed library of glycomimetics designed to bind to C-type lectins like DC-SIGN. We developed a solid phase strategy to synthesize compounds that share a common arrangement of hydroxyl groups yet possess three points of diversity: variation of the amino acid substituent (R1), 1,4-conjugate addition of dithiols (R2), and reaction of benzyl and alkyl bromides with the free thiol (R3). These compounds will be assessed for DC-SIGN binding using a high-throughput fluorescence-based competition assay.
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster
Sci-Mix
Division of Organic Chemistry |
