PPI-368

Chemical Name: (3alpha,5beta,7alpha,12alpha)-Trihydroxycholan-24-oyl-L-leucyl-L-valyl-L-phenylalanyl-L-phenylalanyl-L-alanine
CAS No. 183746-33-0
项目整合开发状态: Biological Testing
项目研究机构: Praecis (Originator)
合成路线:Title compound was synthesized by solid phase peptide synthesis on a Wang resin using N-9-fluorenylmethoxycarbonyl (Fmoc)-protected amino acids.The (Fmoc)alanine-resin (I) was treated with piperidine in N-methylpyrrolidone to yield deprotected alanine-resin (II).Then,condensation with (Fmoc)-phenylalanine (III) using diisopropyl cabodiimide (DIC) and 1-hydroxybenzotriazole (HOBt) as the coupling reagents provided the (Fmoc)-dipeptide resin (IV),which was deprotected as before with piperidine in NMP.The resulting deprotected dipeptide resin (V) was submitted to further sequential amino acid coupling and deprotection cycles with (Fmoc)-phenylalanine (III),(Fmoc)-valine (VII),and (Fmoc)-leucine (IX),to yield in turn resins (VI),(VIII),and (X),respectively.Resin (X) was then coupled with cholic acid (XI) in the presence of DIC and HOBt to give the corresponding amide (XII).

合成路线:Finally,removal of the peptide from the resin was effected by treatment with a mixture of H2O,thioanisole,phenol,and ethanedithiol in trifluoroacetic acid.