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Synthesis of multivalent glycopeptide conjugates that mimic an HIV epitope.

ABSTRACT: Recently, we reported a directed evolution method which enabled us to discover sequences of glycopeptides that bind with picomolar affinity to HIV antibody 2G12 and are of interest as HIV vaccine candidates. In this manuscript, we describe the syntheses of several of these large (~11-12 kDa) glycopeptides by a combination of fast flow peptide synthesis and click chemistry. We also discuss the optimization of their attachment to carrier protein CRM197, affording antigenic and immunogenic conjugates ready for animal vaccination.

SUBMITTER: Bailey JK

PROVIDER: S-EPMC5300091 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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Synthesis of multivalent glycopeptide conjugates that mimic an HIV epitope.

Bailey Jennifer K JK Nguyen Dung N DN Horiya Satoru S Krauss Isaac J IJ

Tetrahedron 20160729 40

Recently, we reported a directed evolution method which enabled us to discover sequences of glycopeptides that bind with picomolar affinity to HIV antibody 2G12 and are of interest as HIV vaccine candidates. In this manuscript, we describe the syntheses of several of these large (~11-12 kDa) glycopeptides by a combination of fast flow peptide synthesis and click chemistry. We also discuss the optimization of their attachment to carrier protein CRM197, affording antigenic and immunogenic conjugat ...[more]

PMID: 28190897

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