Functionalized analogues of an unnatural amino acid that mimics a tripeptide beta-strand

Org Lett. 2008 Nov 20;10(22):5293-6. doi: 10.1021/ol8021897. Epub 2008 Oct 21.

Abstract

This paper introduces polar and hydrophobic variants of the unnatural amino acid Hao, which mimics the hydrogen-bonding functionality of one edge of a beta-strand. In these variants, the methyl side chain of Hao is replaced with acidic, basic, and hydrophobic groups. These modifications can impart improved solubility and additional side-chain interactions to peptides containing Hao.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Amino Acids / chemistry*
  • Amino Acids / metabolism*
  • Biomimetic Materials / chemistry*
  • Biomimetic Materials / metabolism*
  • Hydrogen Bonding
  • Oligopeptides / chemistry*
  • Oligopeptides / metabolism
  • Protein Folding
  • Protein Structure, Secondary
  • Solubility

Substances

  • Amino Acids
  • Oligopeptides