Paul F. Alewood

A novel approach to phosphopeptide synthesis-preparation of glu-pser-leu

Abstract A synthesis of the phosphotripeptide Glu-PSer-Leu is reported via the stepwise incorporation of the protected phosphoamino acid Nα-tert-butoxycarbonyl-o-dibenzylphosphono-L-serine.

Solution-phase synthesis of an O-phosphoseryl-containing peptide using phenyl phosphorotriester protection

The solid-phase synthesis of TFA · H2-Glu-PSer-Leu 1 is reported via incorporation of the protected phosphoroamino acid Nα-tert-butoxycarbonyl-O-(diphenylphosporo)-L-serine 2.

Synthesis of protected derivatives of O-phosphotyrosine incorporation in a heptapeptide

Abstract The solid phase synthesis of the phosphopeptide Leu-Arg-Arg-Ala-Tyr(P)-Leu-Gly is reported via the stepwise incorporation of the protected phosphoamino acid Nα -tert-butyloxycarbonyl-O-dimethyl-phosphono-L-tyrosine.

Synthesis of a Protected Phosphoamino Acid, Nα-tert-Butyloxycarbonyl-O-Diethylphosphoro-L-Serine

Abstract Phosphoproteins are known to play metabolic and structural roles in many biological processes. In such proteins, serine is the most commonly phosphorylated amino acid and is usually flanked by a cluster of acidic or basic residues. In our studies of the structure and reactivity of the phosphorylated segments of the caseins, we have been concerned with the development of a synthetic methodology suitable for the rapid synthesis in gram quantities of phosphopeptides.

Fast atom bombardment mass spectrometry of seryl- and O-phosphoseryl-containing peptides

Abstract FAB-MS was found to be a mild technique for the rapid identification of O—phosphoseryl residues in peptides and the characterization of O—phosphoseryl—containing peptides.

31P NMR SPECTROSCOPY STUDIES ON THE DIORGANYLPHOSPHOROCHLORIDATE/PYRIDINE PHOSPHORYLATION PROCEDURE

Abstract The interaction of diphenyl phosphorochloridate and three dialkyl phosphorochloridates (alkyl = Et, Me, Bzl) with pyridine was shown by 31P NMR spectroscopy to lead to the formation of a diorganyl phosphoropyridinium intermediate. In the case of diethyl, dimethyl and dibenzyl phosphorochloridate, 31P NMR spectroscopy studies showed that their decomposition in pyridine solution resulted from pyridine-mediated dealkylation of the dialkyl phosphoropyridinium intermediate followed by the generation of diphosphate and triphosphate species. The use of the sterically hindered bases, 2-methyl-pyridine and 2,6-dimethylpyridine, showed that increased steric hindrance of the tertiary base caused a significant reduction in the extent of decomposition of the dialkyl phosphoro-N-pyridinium intermediate.

N-acetyl-N-oxo-1,4-benzoquinone imine, observation of an acyl nitrone

Abstract N-Acetyl-N-oxo-1,4-benzoquinone imine, an N-acyl nitrone has been prepared and its intramolecular rearrangement to N-acetoxy-1,4-benzoquinone imine observed using 1 H-NMR spectroscopy.