Side reactions in solid phase synthesis of histidine-containing peptides. Characterization of two major impurities by sample displacement chromatography and FAB-MS.
The flow-polyamide synthesis of a histidine-containing sequence (Ac-YDNVLDHLTGR) produced two major impurities which were isolated through Sample Displacement Chromatography and characterized by Fast Atom Bombardment-mass analysis. The impurities correspond to the sequence Ac-YDNVLDH, and to a peptide with the Asp residue cyclized to a succinimide. The latter side-reaction took place during the acetylation procedure, and demands attention where capping procedures are planned in the synthesis of Asp-His sequences.
Pessi
A
A
Peptide Synthesis Unit, SCLAVO SpA, Rome, Italy.
Mancini
V
V
Filtri
P
P
Chiappinelli
L
L
D000595:Amino Acid Sequence; D001224:Aspartic Acid / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D006639:Histidine / Q000737:chemistry*; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013388:Succinimides / Q000737:chemistry
D010455:Peptides; D013388:Succinimides; C032620:succinimide; D001224:Aspartic Acid; D006639:Histidine