Unexpected stability of the urea cis-trans isomer in urea-containing model pseudopeptides

Org Lett. 2001 Nov 29;3(24):3843-6. doi: 10.1021/ol0166552.

Abstract

In contrast to the situation observed in the crystal state, the urea moiety in N-Boc-N'-carbamoyl-gem-diaminoalkyl derivatives (single-residue ureidopeptides) 1-4 exclusively assumes a cis-trans conformation in solution. When R(3) = H, the resulting structure can be further stabilized by an intramolecular hydrogen bond that closes an eight-membered pseudocycle. The root-mean-square deviation calculated for heavy atoms between a peptide gamma-turn and the folded conformation that we propose to call urea turn is 0.60 A. [structure: see text]

MeSH terms

  • Isomerism
  • Models, Chemical*
  • Peptides / chemistry*
  • Urea / chemistry*

Substances

  • Peptides
  • Urea