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  • Title: [Side reactions in peptide synthesis. V. O-sulfonation of serine and threonine during removal of pmc- and mtr-protecting groups from arginine residues in fmoc-solid phase synthesis].
    Author: Jaeger E, Remmer HA, Jung G, Metzger J, Oberthür W, Rücknagel KP, Schäfer W, Sonnenbichler J, Zetl I.
    Journal: Biol Chem Hoppe Seyler; 1993 May; 374(5):349-62. PubMed ID: 8338636.
    Abstract:
    A novel side reaction in Fmoc-solid-phase synthesis, which occurs during removal of protecting groups and detachment from the resin, was elucidated by investigations on model peptides: During the cleavage of Pmc- or Mtr-protecting groups from arginine residues by trifluoroacetic acid in peptides with O-tert-butyl-protected aliphatic hydroxyamino acids, peptides containing O3-sulfo-serine and O3-sulfo-threonine are formed as side-products in high yields, if suitable scavengers are absent. Subsequent to their isolation and purification, the structures of these peptide sulfuric acid mono-esters could unequivocally be proven by chemical and spectroscopic (MS, NMR, IR) methods.
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