Proof of delocalization-stabilization by sulfur in enolate formation during racemisation of sulfur containing amino acid residues.

✍ Scribed by M.J.O. Anteunis; F. Borremans; D. Wante; R. Schrooten

• Book ID: 104234170
• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 215 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81838-4

✦ Synopsis

The present kinetic data on the accelerating action of sulfur in the base catalyzed racemisation of cyclic dipeptides (2) support the explanation of Barber and Jones (t) for the c1 center and suggest further a 1,3-and 1,4-interaction of -S-with the amide N-atom (,$) for the CI' center

The problem of ease of racemisation is paramount for the success of peptide synthesis whereby often active esters of amino acids that are optically labile have to be used.