Coworker: Miss Nadine Jede

Task:
Solid phase synthesis of a tetrapeptide Trp-Met-Asp-Phe-NH₂.
This tetrapeptide exists in the carboxyl terminal of cholecystokinin (CCK-4), gastrin and caerulein. Structure-Activity-Relationship studies show that this tetrapeptide is the active center of those hormones. In Prof L. F. Tietze’s group, we use this tetrapeptide as a part of the prodrug of CC-1065 analogues, which have high anti-cancer activity. And before we have synthesized this tetrapeptide using solution method.

Procedure:
I tried syntheses both with synthetic machine and manually.
Resin: Rink Amide Resin, loading: 0.57 mmol/g
Standard Fmoc-SPPS
Coupling reagents: HOBt, HBTU, DIPEA
Cleavage from the resin: TFA, H₂O, EDT, thioanisol, anisol, TIS
Analysis by HPLC: Jsphere ODS/H80_25cm_analytical

Results:
The MS result shows the correct molecular peak.
The HPLC result shows that the main peak has the same retention time as the commercially available sample.


April 23 2004