[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].
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.
Jaeger
E
E
Max-Planck-Institut für Biochemie, Martinsried.
Remmer
H A
HA
Jung
G
G
Metzger
J
J
Oberthür
W
W
Rücknagel
K P
KP
Schäfer
W
W
Sonnenbichler
J
J
Zetl
I
I
D000595:Amino Acid Sequence; D001120:Arginine / Q000737:chemistry*; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D002852:Chromatography, Ion Exchange; D016166:Free Radical Scavengers; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D012694:Serine / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013912:Threonine / Q000737:chemistry*
D016166:Free Radical Scavengers; D007202:Indicators and Reagents; D010455:Peptides; D013912:Threonine; D012694:Serine; D001120:Arginine
Nebenreaktionen bei Peptidsynthesen, V. O-Sulfonierung von Serin und Threonin während der Abspaltung der Pmc- und Mtr-Schutzgruppen von Argininresten bei Fmoc-Festphasen-Synthesen.