Conformationally constrained aliphatic-aromatic amino-acid-conjugated hybrid foldamers with periodic beta-turn motifs

J Org Chem. 2007 Aug 31;72(18):7022-5. doi: 10.1021/jo0709044. Epub 2007 Aug 10.

Abstract

In this note, we describe the design, synthesis, and structural studies of novel hybrid foldamers derived from Aib-Pro-Adb building blocks that display repeat beta-turn structure motif. The foldamer having a conformationally constrained aliphatic-aromatic amino acid conjugate adopts a well-defined, compact, three-dimensional structure, governed by a combined conformational restriction imposed by the individual amino acids with which it is made of. Conformational investigations by single-crystal X-ray and solution-state NMR studies were undertaken to investigate the conformational preference of these foldamers with a hetero-backbone. Our findings suggest that constrained aliphatic-aromatic amino acid conjugates would offer new avenues for the de novo design of hybrid foldamers with distinctive structural architectures.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids, Aromatic / chemistry*
  • Crystallography, X-Ray
  • Fatty Acids / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Protein Structure, Tertiary
  • Titrimetry

Substances

  • Amino Acids, Aromatic
  • Fatty Acids