The amine capture strategy for peptide bond formation—an outline of progress

✍ Scribed by D. S. Kemp

• Publisher: Wiley (John Wiley & Sons)
• Year: 1981
• Tongue: English
• Weight: 628 KB
• Volume: 20
• Category: Article
• ISSN: 0006-3525
• DOI: 10.1002/bip.1981.360200904

✦ Synopsis

Abstract

A review is presented of the general features of amide bond formation by prior capture of the amine‐bearing peptide fragment. Capture by formation of a bond to the N‐terminal nitrogen is shown in eight model systems to result in slow intramolecular acyl transfer, accompanied by anomalously large Gly/Ala and Gly/Val rate ratios. Two examples are given of rapid intramolecular acyl transfer via rings of 9 and 12 members. The transfer efficiency as estimated by the effective molarity of reactive amine at the acyl carbon in the latter case is 18__M__. Capture at the thiol function of an N‐terminal cysteine residue is shown to be feasible in mercurithio and disulfide systems. In the latter case, effective concentrations of 3__M__ and intramolecular transfer half‐times of 10 min are demonstrated.