Protease-catalyzed synthesis of the tripeptide CCK sub(26-28), a fragment of CCK-8

• Published in: Amino acids Vol. 33; no. 1; pp. 91 - 96
• Main Authors: Meng, L P, Joshi, R, Eckstein, H
• Format: Journal Article
• Language: English
• Published: 01.07.2007
• Subjects: Amino acids; Derivatives; Esters; Fragmentation; Gain; Nucleophiles; Strategy; Synthesis
• DOI: 10.1007/s00726-006-0421-z
• ISSN: 0939-4451

Two enzymatically synthetic strategies of the tripeptide derivative PhAc-Asp(OMe)-Tyr-Met-OAl are reported. The second strategy gains the advantage of more economical starting materials, less reaction steps and a higher overall isolated yield of this tripeptide fragment over the first strategy. The effect of the acyl-donor ester concentration and structure, the C- alpha protecting group of the nucleophile, reaction media, enzyme and the carrier on the tripeptide derivative synthesis were studied. This tripeptide selected is a fragment of the cholecystokinin C-terminal octapeptide (CCK-8), a potential therapeutic agent in the control of gastrointestinal function and also a drug candidate for the treatment of epilepsy.