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Application of 2‐chlorotrityl resin in solid phase synthesis of (Leu 15 )‐gastrin I and unsulfated cholecystokinin octapeptide

1991; Wiley; Volume: 38; Issue: 6 Linguagem: Inglês

10.1111/j.1399-3011.1991.tb01539.x

0367-8377

Kleomenis Barlos, Dimitrios Gatos, STAVROS KAPOLOS, Constantine Poulos, Wolfram Schäfer, Wenqing Yao,

Peptidase Inhibition and Analysis

The carboxyl terminal dipeptide amide, Fmoc‐Asp‐Phe‐NH 2 , of gastrin and cholecystokinin (CCK) has been attached in high yield through its free side chain carboxyl group to the acid labile 2‐chlorotrityl resin. The obtained peptide resin ester has been applied in the solid phase synthesis of partially protected (Leu 15 )‐gastrin I utilising Fmoc‐amino acids. Quantitative cleavage of this peptide from resin, with the t‐butyl type side chain protection intact is achieved using mixtures of acetic acid/trifluoroethanol/dichloro‐methane. Under the same conditions complete detritylation of the tyrosine phenoxy function occurs simultaneously. Thus, the solid‐phase synthesis of peptides selectively deprotected at the side chain of tyrosine is rendered possible by the use of 2‐chlorotrityl resin and Fmoc‐Tyr(Trt)‐OH. The efficiency of this approach has been proved by the subsequent high‐yield synthesis of three model peptides and the CCK‐octapeptide.