Stereoselective self-sorting in the self-assembly of a Phe-Phe extended guanidiniocarbonyl pyrrole carboxylate zwitterion: formation of two diastereomeric dimers with significantly different stabilities

Chem Commun (Camb). 2011 Jul 28;47(28):7953-5. doi: 10.1039/c1cc12520f. Epub 2011 Jun 13.

Abstract

The 'dipeptide extended' guanidiniocarbonyl pyrrole carboxylate zwitterion GCP-Phe-Phe 1 forms stable dimers in DMSO. However, dimerization is highly stereoselective. Only homochiral dimers are formed and the (L,L)·(L,L) dimer (K(dim) > 10(5) M(-1)) is significantly more stable by a factor of 10(3) than the diastereomeric (D,L)·(D,L) dimer (K(dim) = 120 M(-1)).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxylic Acids / chemistry*
  • Dimerization*
  • Dipeptides / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Phenylalanine / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Carboxylic Acids
  • Dipeptides
  • guanidiniocarbonyl pyrrole carboxylate-phenylalanyl-phenylalanine
  • Phenylalanine