Crystal structure and conformation of L-pyroglutamyl-L-alanine

Int J Pept Protein Res. 1989 May;33(5):328-34. doi: 10.1111/j.1399-3011.1989.tb00689.x.

Abstract

Crystals of the dipeptide, pyroglutamyl-alanine (C8H12N2O4) grown from aqueous methanol are monoclinic, space group P2(1) with the following cell parameters: a = 4.863(2), b = 16.069(1), c = 6.534(2)A and beta = 109.9(2) degrees, V = 480.0A3, Mr = 200.2, Dc = 1.385 g cm-3, and Z = 2. The crystal structure was solved by the application of direct methods and refined to an R value of 0.044 for 699 reflections with I greater than 2 sigma. The amide of the pyroglutamyl side chain is cis, omega 1 = 2.6(7) degrees; the peptide unit is trans and appreciably non-planar (omega 2 = 167.4(5) degrees). The backbone torsional angles are: psi 1 = 166.1(5), phi 2 = -90.3(6), and psi 2 = -22.4(6) degrees. This structure contains a short (2.551(5)A) intermolecular hydrogen bond between the carboxyl OH and the N-acyl oxygen, a feature common to most acyl amino acids and acyl peptides.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Chemical Phenomena
  • Chemistry
  • Crystallography
  • Dipeptides / analysis*
  • Hydrogen Bonding
  • Protein Conformation
  • Pyrrolidonecarboxylic Acid / analogs & derivatives
  • Software

Substances

  • Dipeptides
  • L-pyroglutamyl-L-alanine
  • Pyrrolidonecarboxylic Acid