Further studies into the Boc/solid-phase synthesis of Ser(P)- and Thr(P)-containing peptides.
The Ser(P)-containing peptide corresponding to phospholamban 11-19, Ac-Ala-Ile-Arg-Arg-Ala-Ser(P)-Thr-Ile-Glu-NH2, was prepared by the use of Boc-Ser(PO3Ph2)-OH in Boc/solid-phase peptide synthesis followed by HF cleavage of the peptide from the polystyrene resin and subsequent platinum-mediated hydrogenolytic cleavage of the phenyl phosphate groups. A study of the HF deprotection step showed that extensive dephosphorylation of the Ser(PO3Ph2)-residue occurred using three commonly used HF conditions and gave rise to large quantities of the Ser-containing peptide. The subsequent study of model peptide systems under standard HF conditions established firstly that the extent of dephosphorylation was dependent on the HF-contact time, and secondly that the Ser(PO3Ph2) residue underwent dephosphorylation at a slightly higher rate than the Thr(PO3Ph2) residue.
Perich
J W
JW
Centre of Pharmacology-Endocrinology, CNRS-INSERM, Montpellier, France.
Terzi
E
E
Carnazzi
E
E
Seyer
R
R
Trifilieff
E
E
D000595:Amino Acid Sequence; D005563:Formic Acid Esters / Q000737:chemistry*; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis*; D010766:Phosphorylation; D010768:Phosphoserine / Q000737:chemistry*; D010769:Phosphothreonine / Q000737:chemistry*
D005563:Formic Acid Esters; D010455:Peptides; C000345:t-butyloxycarbonyl group; D010769:Phosphothreonine; D010768:Phosphoserine