title: A method for S- and O-palmitoylation of peptides: synthesis of pulmonary surfactant protein-C models.
abstract: A method for O- and S-palmitoylation of non-protected peptides has been developed. The peptides are treated with excess of palmitoyl chloride in 100% trifluoroacetic acid for 10 min at room temperature. The acidic conditions prevent acylation of amino groups, which is only significant after prolonged treatment (hours to days). The tripeptides Gly-Cys-Phe and Gly-Ser-Phe were converted into the respective S- and O-palmitoylated compounds, and the hydrophobic pulmonary surfactant protein-C model peptides, LRIPCCPVNLKRLLVVV [SP-C(1-17)] and FGIPSSPVLKRLLILLLLLLLILLLILGALLMGL [SP-C(Leu)] were converted into their respective S,S- and O,O-dipalmitoylated peptides. The reactions were virtually quantitative, and the palmitoylated peptides were isolated in about 75-80% yield after reversed-phase HPLC purification. CD spectroscopy showed that S, S-dipalmitoylation of SP-C(1-17) affects the peptide secondary structure (substantial increase in the alpha-helix content) in dodecylphosphocholine micelles.
authors.affiliation: Division of Organic and Bioorganic Chemistry, Department of Medical Biochemistry and Biophysics, Karolinska Institutet, S-17177, Stockholm, Sweden.
authors.forename: E
authors.initials: E
authors.lastname: Yousefi-Salakdeh
authors.forename: J
authors.initials: J
authors.lastname: Johansson
authors.forename: R
authors.initials: R
authors.lastname: Strömberg
mesh_terms: D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D019308:Palmitic Acid / Q000737:chemistry* / Q000378:metabolism; D010446:Peptide Fragments / Q000138:chemical synthesis / Q000737:chemistry; D011487:Protein Conformation; D011499:Protein Processing, Post-Translational; D011510:Proteolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D011663:Pulmonary Surfactants / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
chemical_list: D006020:Glycopeptides; D007202:Indicators and Reagents; D009842:Oligopeptides; D010446:Peptide Fragments; D011510:Proteolipids; D011663:Pulmonary Surfactants; D019308:Palmitic Acid