A shape-persistent D,L-dipeptide building block for the assembly of rigidified oligopeptides

Org Biomol Chem. 2006 Dec 21;4(24):4491-6. doi: 10.1039/b613172g. Epub 2006 Nov 9.

Abstract

Mannuronic acid (5) was transformed into the densely functionalised D,L-dipeptide mimic 1 and subsequently inserted into the cyclic hexapeptide 3. The gulo-configurated seven-membered lactam 1 exhibits an inverted ring conformation compared to the previously described L,L-dipeptide mimic 2. In spite of this considerable difference, both prefer the same i to i + 1 positions of a beta-turn within a cyclic hexapeptide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Dipeptides / chemistry*
  • Models, Molecular
  • Oligopeptides / chemistry*
  • Protein Conformation

Substances

  • Dipeptides
  • Oligopeptides