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.
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.
Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India. absk@chem.iitkgp.ernet.in
Amit
A
Basak
Subhendu Sekhar
SS
Bag
Hussam M M
HM
Bdour
D000475:Alkenes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002152:Calorimetry, Differential Scanning; D003500:Cyclization; D006860:Hydrogen Bonding; D008958:Models, Molecular; D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D055672:Static Electricity; D013816:Thermodynamics
D000475:Alkenes; D000480:Alkynes; D000596:Amino Acids; D009842:Oligopeptides