beta-Alanyl-beta-alanine in cyclic beta-turned peptides

Biopolymers. 1991 Sep;31(10):1181-8. doi: 10.1002/bip.360311006.

Abstract

In the present paper we describe the synthesis, purification, and single crystal x-ray analysis of the cyclic pentapeptide cyclo-(L-Pro-L-Pro-L-Phe-beta-Ala-beta-Ala). The peptide was synthesized by classical solution methods and the cyclization of the free pentapeptide was accomplished in good yields in diluted methylene-chloride solution using N,N-dicyclohexylcarbodiimide. The compound crystallizes in the monoclinic space group P21 from hot water with five solvent molecules. The Pro1-Pro2 peptide bond is cis and the molecular conformation is stabilized by an intramolecular hydrogen bond between the CO group of the beta-Ala5 and the NH of the Phe3 residue. The Pro1-Pro2 segment occupies the relative positions 2 and 3 of a type VIa beta-turn, while the L-phenylalanyl-beta-alanyl-beta-alanine segment is incorporated in a C13-like ring structure. The crystal packing is characterized by a network of 11 intermolecular hydrogen bonds involving all the remaining CO, NH, and the water molecules.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography*
  • Depsipeptides*
  • Models, Molecular
  • Molecular Conformation
  • Peptides, Cyclic / chemistry*
  • beta-Alanine / chemistry*

Substances

  • Depsipeptides
  • Peptides, Cyclic
  • beta-Alanine
  • roseotoxin B
  • destruxin B