Synthesis and reactivity of enediynyl amino acids and peptides: a novel concept in lowering the activation energy of Bergman cyclisation by H-bonding and electrostatic interactions

Chem Commun (Camb). 2003 Oct 21:(20):2614-5. doi: 10.1039/b308976m.

Abstract

Novel enediynyl amino acids and peptides 3 and 5-8 were synthesized and their thermal reactivity towards Bergman cyclization studied and compared with the earlier reported amino acid 4, which demonstrated, for the first time, the effect of H-bonding and electrostatic interactions in lowering the activation energy of Bergman cyclization.

Publication types

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

MeSH terms

  • Alkenes / chemistry
  • Alkynes / chemistry*
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Calorimetry, Differential Scanning
  • Cyclization
  • Hydrogen Bonding
  • Models, Molecular
  • Nuclear Magnetic Resonance, Biomolecular / methods
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Static Electricity
  • Thermodynamics

Substances

  • Alkenes
  • Alkynes
  • Amino Acids
  • Oligopeptides