Deprotection of the S-trimethylacetamidomethyl (Tacm) group using silver tetrafluoroborate: application to the synthesis of porcine brain natriuretic peptide-32 (pBNP-32).

  title={Deprotection of the S-trimethylacetamidomethyl (Tacm) group using silver tetrafluoroborate: application to the synthesis of porcine brain natriuretic peptide-32 (pBNP-32).},
  author={M. Yoshida and Tadashi Tatsumi and Yoichi Fujiwara and Satoshi Iinuma and T. Kimura and Kenichi Akaji and Yoshiaki Kiso},
  journal={Chemical \& pharmaceutical bulletin},
  volume={38 6},
Silver tetrafluoroborate (AgBF4) 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 AgBF4 deprotection. The synthetic pBNP-32 was obtained in better yield by the AgBF4 procedure than by the standard I2 procedure. The synthetic… 
20 Citations
Syntheses of Natriuretic Peptides Using a New S -Protecting Group, S -Trimethylacetamidomethyl (Tacm) Group
The preparation and characterization of a new S-protecting group, the S-trimethylacetamidomethyl (Tacm) group, is described and its application to the syntheses of natriuretic peptides is described.
p-Nitrobenzyl protection for cysteine and selenocysteine: a more stable alternative to the acetamidomethyl group.
The occasionally described Acm instability is confirmed and underpins the development of the p-nitrobenzyl group as an alternative for cysteine and Sec protection.
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Transition metals such as Pd, Ag, Hg, Tl, Au, Zn, Ni, and Cu have also contributed to the field of peptide and protein synthesis such as in peptide conjugation, extending native chemical ligation, and for regioselective disulfide bonds formation.
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