Novel peptoid building blocks: synthesis of functionalized aromatic helix-inducing submonomers

Org Lett. 2010 Feb 5;12(3):492-5. doi: 10.1021/ol902660p.

Abstract

Peptoids, oligo-N-substituted glycines, can fold into well-defined helical secondary structures. The design and synthesis of new peptoid building blocks that are capable of both (a) inducing a helical secondary structure and (b) decorating the helices with chemical functionalities are reported. Peptoid heptamers containing carboxamide, carboxylic acid or thiol functionalities were synthesized, and the resulting peptoids were shown to form stable helices. A thiol-containing peptoid readily formed the homodisulfide, providing a convenient route to prepare peptoid helix homodimers.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Models, Molecular*
  • Molecular Structure
  • Peptoids / chemical synthesis*
  • Peptoids / chemistry
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry

Substances

  • Peptoids
  • Sulfhydryl Compounds