Organic approaches to nanotechnology through nanometer-scale amino acids

ORGN 390

James S. Nowick, jsnowick@uci.edu, Chris M. Gothard, cgothard@uci.edu, Sang-Woo Kang, and Santanu Mairita. Department of Chemistry, University of California, Irvine, 4126 Natural Sciences 1, Irvine, CA 92697-2025

Functionalized derivatives of the nanometer-scale amino acids aminobiphenylcarboxylic acid (Abc) and aminodiphenylmethanecarboxylic acid (Adc) are ideal building blocks for the chemical synthesis of nanometer-scale structures. The amino acid Abc2K is 1.0-nm long, rigid, and linear, while the amino acid AdcK is 1.0-nm long, rigid, and bent. Both amino acids can be readily prepared in protected forms (Fmoc-Abc2K(Boc)-OH and Fmoc-AdcK(Boc)-OH) that are fully compatible with standard Fmoc-based solid-phase peptide synthesis techniques. Peptides derived from these amino acids are water-soluble, can be purified by RP-HPLC, and are readily characterized by 1H NMR spectroscopy and ESI-MS techniques. Peptides based on Abc2K form nanometer-scale rods, while cyclic peptides based on AdcK form nanometer-scale rings that serve as molecular receptors. This presentation will describe ongoing studies of the synthesis, structure, and function of peptides based on these nanometer-scale amino acids.