Detection and control of aspartimide formation in the synthesis of cyclic peptides

Bioorg Med Chem Lett. 2005 Feb 15;15(4):1065-8. doi: 10.1016/j.bmcl.2004.12.025.

Abstract

Extensive two-dimensional NMR analysis was employed to characterize the structural identity of the macrocyclic peptide lactam and the imide analog, a major side reaction product when allyl ester was used to protect the side chain of aspartic acid. A straightforward protocol modification was developed to minimize aspartimide formation during the synthesis of cyclic peptides.

MeSH terms

  • Aspartic Acid* / analogs & derivatives*
  • Combinatorial Chemistry Techniques
  • Lactams
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / isolation & purification
  • Quality Control

Substances

  • Lactams
  • Peptides, Cyclic
  • Aspartic Acid
  • aspartimide