Synthesis of human C-type natriuretic peptide 22 using chlorotrityl resin and tetrafluoroboric acid deprotection.
Human C-type natriuretic peptide 22 (hCNP22), the third member of the natriuretic peptide family, was efficiently synthesized by Fmoc-based peptide chain construction on a 2-chlorotrityl (Clt) resin, followed by deprotection using tetrafluoroboric acid (HBF4). The use of Clt resin was effective in suppressing racemization at the C-terminal cysteine residue caused by the base treatment for Fmoc-cleavage. The disulfide bond of hCNP22 was constructed using the silyl chloride-sulfoxide method to avoid oxidation at the Met residue. Using amino acid- and dipeptide-resin derivatives, the effects of bases, protecting groups and resin supports on the racemization at the C-terminal Cys residue were examined in detail.
Fujiwara
Y
Y
Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Japan.
Yokotani
J
J
Akaji
K
K
Kiso
Y
Y
D000595:Amino Acid Sequence; D009320:Atrial Natriuretic Factor / Q000138:chemical synthesis*; D001881:Borates; D001888:Boric Acids / Q000737:chemistry; D003545:Cysteine / Q000737:chemistry; D006801:Humans; D008969:Molecular Sequence Data; D020098:Natriuretic Peptide, C-Type; D011506:Proteins / Q000138:chemical synthesis*; D012116:Resins, Plant / Q000737:chemistry
D001881:Borates; D001888:Boric Acids; D011506:Proteins; D012116:Resins, Plant; D020098:Natriuretic Peptide, C-Type; D009320:Atrial Natriuretic Factor; C098759:fluoroboric acid; D003545:Cysteine