Protease-catalyzed synthesis of the tripeptide CCK(26-28), a fragment of CCK-8.
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.
Meng
L P
LP
Pharmacy School of Tongji Medical College, HUST, Wuhan, China.
Joshi
R
R
Eckstein
H
H
D002918:Chymotrypsin / Q000378:metabolism*; D009842:Oligopeptides / Q000138:chemical synthesis*; D010206:Papain / Q000378:metabolism*; D010446:Peptide Fragments / Q000138:chemical synthesis; D012844:Sincalide / Q000737:chemistry*; D013820:Thermolysin / Q000494:pharmacology*
D009842:Oligopeptides; D010446:Peptide Fragments; D002918:Chymotrypsin; D010206:Papain; D013820:Thermolysin; D012844:Sincalide