Deprotection of the S-Trimetylacetamidomethyl (Tacm) Group Using Silver Tetrafluoroborate : : Application to the Synthesis of Porcine Brain Natriuretic Peptide-32 (pBNP-32)

概要

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Silver tetrafluoroborate (AgBF_4) in trifluoroacetic acid (TFA) has been found to cleave the S-trimethyl-acetamidomethyl (Tacm) group or the S-acetamidomethyl (Acm) group without affecting other functional groups in a peptide chain. A newly isolated porcine brain natriuretic peptide-32 (pBNP-32) was synthesized by the combined use of the S-Tacm group and AgBF_4 deprotection. The synthetic pBNP-32 was obtained in better yield by the AgBF_4 procedure than by the standard I_2 procedure. THe syntehtic pBNP-32 has the highest chick rectum relaxant activity among the known members of the atrial natriuretic peptide-brain natriuretic peptide (ANP-BNP) families.Somatostatin was also synthesized by the Fmoc-based solid-phase method usign S-Tacm and AgBF_4. In this synthesis, the recently developed reagent tetrafluoroboric acid(HBF_4)was applied to cleave the peptide from the resin.
公益社団法人日本薬学会の論文
1990-06-25