Further studies on the use of 2,2,2-trichloroethyl groups for phosphate protection in phosphoserine peptide synthesis.
Boc-Ser(PO3Tc2)-OH, Z-Ser(PO3Tc2)-OH and Fmoc-Ser(PO3Tc2)-OH, derivatives useful for peptide synthesis, have been obtained in high yields by acylation of H-Ser(PO3Tc2)-OH.CF3COOH. The latter was obtained from Boc- or Z-Ser(PO3Tc2)-OBzl by simultaneous removal of the amino- and carboxy-protecting groups by Pd-catalyzed hydrogenolysis in acetic acid-trifluoroacetic acid solution. Removal of the Tc-protecting group was efficiently achieved by hydrogenolysis in aqueous ethanol.
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Food Research Centre, Department of Agriculture, Ottawa, Ontario, Canada.
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D010710:Phosphates / Q000737:chemistry; D010768:Phosphoserine / Q000737:chemistry*
D000596:Amino Acids; D010455:Peptides; D010710:Phosphates; D010768:Phosphoserine