First 3-D structure determination of a peptide oxazol-5(4H)-one with a chiral protein amino acid in the heterocyclic moiety: an x-ray diffraction analysis of the enantiomeric and racemic Goodman oxazolone

Pept Res. 1995 May-Jun;8(3):187-90.

Abstract

The x-ray diffraction structure analyses of the L-enantiomeric and racemic forms of the 2-(1'-benzyloxycarbonylamino-1'-methyl) ethyl-4-benzyl-oxazol-5(4H)-one, the Goodman oxazolone, have been performed. In the crystal state the oxazolone ring of the enantiomeric compound is nearly sandwiched between the two phenyl rings, whereas in the racemate the phenyl ring of the N alpha-protecting group moves away from the oxazolone ring.

Publication types

  • Comparative Study

MeSH terms

  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Oxazoles / chemical synthesis
  • Oxazoles / chemistry*
  • Stereoisomerism

Substances

  • 2-(1'-benzyloxycarbonylamino-1'-methyl)ethyl-4-benzyloxazol-5(4H)-one
  • Oxazoles