A cysteine-derived acrylamide platform was envisaged as a chemical core to which lipid and peptide ligands or reporter groups could be readily attached in a highly modular process. The core was prepared via cyclization of L-cysteine with <i>m</i>-nitrobenzaldehyde followed by acylation with acryloyl chloride yielding a trifunctionalized thiazolidine with carboxylic acid, aryl nitro, and acryloyl substituents. Thiol lipid modules were conjugated to the thiazolidine acrylamide and the nitro group was reduced to the corresponding amine followed by Fmoc protection, generating a novel cysteine lipid analogue (CLA). The CLA construct was submitted to solid-phase peptide synthesis (SPPS) for the synthesis of lipopeptides. With this synthetic technology we are preparing an array of custom lipopeptides capable of serving as targeting ligands, with drug releasing capabilities, in nanovectors for combination therapies.<br/>Partially funded by NIGMS RISE GM060655.

Modular platform for the synthesis of a targeting and pH-responsive lipopeptide ligand in nanovectors

249th National Meeting (2015)

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