Studies on peptides. CLX. Synthesis of a 33-residue peptide corresponding to the entire amino acid sequence of human cholecystokinin (hCCK-33).

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An unsulfated form of human cholecystokinin (hCCK-33) was synthesized by successive azide condensations of seven peptide fragments, followed by deprotection with 1 M trimethylsilyl trifluoromethanesulfonate/trifluoroacetic acid. The phenolic group of Tyr (position 27) was selectively sulfated with pyridine-SO3 complex, after reversible masking of other functional groups with hard base (F-)-labile protecting groups, i.e., the amino functions with 9-fluorenyl-methyloxycarbonyl group and the hydroxyl functions of 4 Ser residues with tert-butyldiphenylsilyl groups. In terms of pancreatic protein output and capillary blood flow in dogs, the relative potency of synthetic hCCK-33 with respect to that of synthetic CCK-8 (taken as 1 on a molar basis) was 0.9. In terms of gastric acid and pepsin output in rat in vivo assays, synthetic hCCK-33 was about 2- to 3-fold more potent than CCK-8 on a molar basis.

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