Deprotection of the S-trimethylacetamidomethyl (Tacm) group using silver tetrafluoroborate: application to the synthesis of porcine brain natriuretic peptide-32 (pBNP-32).
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 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 using S-Tacm and AgBF4. In this synthesis, the recently developed reagent tetrafluoroboric acid (HBF4) was applied to cleave the peptide from the resin.
Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Japan.
M
M
Yoshida
T
T
Tatsumi
Y
Y
Fujiwara
S
S
Iinuma
T
T
Kimura
K
K
Akaji
Y
Y
Kiso
D000081:Acetamides; D000595:Amino Acid Sequence; D000818:Animals; D001881:Borates; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D020097:Natriuretic Peptide, Brain; D009419:Nerve Tissue Proteins / Q000138:chemical synthesis*; D012834:Silver; D018030:Silver Compounds; D013552:Swine
D000081:Acetamides; D001881:Borates; D007202:Indicators and Reagents; D009419:Nerve Tissue Proteins; D018030:Silver Compounds; D020097:Natriuretic Peptide, Brain; C064097:silver tetrafluoroborate; D012834:Silver