Identification of a sequence-dependent reversible acylation of tosylarginine in a peptidyl-resin reacted with isonicotinyl p-nitrophenylcarbonate.
In this paper, we report on the identification of an unexpected acylation that occurred on the solid phase when a peptide containing an unprotected lysyl and a tosyl-protected arginyl residue was treated with a large excess of isonicotinyl p-nitrophenylcarbonate. NMR and matrix-assisted laser desorption/ionisation -post-source decay analysis of the purified peptide demonstrated the presence of one extra isonicotinyloxycarbonyl (iNoc) group located on the omega nitrogen atom of the arginine which was adjacent to the Lys(iNoc). The desired peptide was obtained by quantitative removal of the unwanted iNoc group during a brief treatment with diluted aqueous hydrazine.
Melnyk
O
O
Laboratoire de Synthèse, Structure et Fouction des Biomolécules associé au CNRS, URA 1309, Institut Pasteur de Lille/Institut de Biologie de Lille, France.
Chaurand
P
P
Rommens
C
C
Drobecq
H
H
Wieruszeski
J M
JM
Spengler
B
B
Gras-Masse
H
H
D000215:Acylation; D000595:Amino Acid Sequence; D001120:Arginine / Q000031:analogs & derivatives* / Q000737:chemistry; D007539:Isonicotinic Acids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009578:Nitrobenzenes / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D012116:Resins, Plant / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D007539:Isonicotinic Acids; D009578:Nitrobenzenes; D010455:Peptides; D012116:Resins, Plant; C112070:isonicotinyl 4-nitrophenylcarbonate; D001120:Arginine