Solution-phase synthesis of porcine brain natriuretic peptide (pBNP) using S-trimethylacetamidomethylcysteine.
The hexadodecapeptide corresponding to the entire amino acid sequence of porcine brain natriuretic peptide (pBNP) was synthesized by assembling four segments in solution, followed by HF deprotection and subsequent oxidation to establish an intramolecular disulfide bridge. The synthesis using the newly developed S-trimethylacetamidomethylcysteine [Cys(Tacm)] derivative gave a better yield than that using the S-2,4,6-trimethylbenzylcysteine [Cys(Tmb)] derivative. The chick rectum relaxant activity of the synthetic pBNP was 2.9 times more potent than that of alpha-rat atrial natriuretic peptide (alpha-rANP).
Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Japan.
Y
Y
Kiso
M
M
Yoshida
T
T
Kimura
Y
Y
Fujiwara
M
M
Shimokura
K
K
Akaji
D000595:Amino Acid Sequence; D000818:Animals; D003545:Cysteine / Q000031:analogs & derivatives*; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D020097:Natriuretic Peptide, Brain; D009419:Nerve Tissue Proteins / Q000138:chemical synthesis*; D013552:Swine
D007202:Indicators and Reagents; D009419:Nerve Tissue Proteins; D020097:Natriuretic Peptide, Brain; C065465:trimethylacetamidomethylcysteine; D003545:Cysteine