Solution-Phase Synthesis of Porcine Brain Natriuretic Peptide (pBNP) Using S-Trimethylacetamido-methylcysteine

Abstract

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 and intramolecular disulfide bridge. The synthesis using the newly developed S-trimethylacetamido-methylcysteine [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 α-rat atrial natriuretic peptide (α-rANP).