Acylation of peptide hydroxyl groups with the Bolton-Hunter reagent.
Reaction of the decapeptide gonadotropin releasing hormone (GnRH) with the Bolton-Hunter reagent produced a single major derivative. Mass spectrometric analysis of this derivative at M-Scan Corporation revealed that O-acylation of the Ser4 hydroxyl had occurred. Formation of the O-acylated Ser4 derivative was dependent on the presence of the His2 residue in GnRH. Similar experiments with several unrelated peptides revealed that the Bolton-Hunter reagent will readily acylate hydroxyl groups on serine, tyrosine, and threonine side chains located two positions from a histidine residue (e.g., His-X-Ser). Such O-acylated peptides can be formed under mild reaction conditions and appear to be relatively stable. Recognition of this sequence-specific O-acylation can be critical when labeling peptides with the Bolton-Hunter reagent and when interpreting experiments in which such modified peptides are used.
Miller
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Department of Anatomy & Neurosciences, University of Texas Medical Branch, Galveston 77555-1043, USA.
D000215:Acylation; D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D007987:Gonadotropin-Releasing Hormone / Q000737:chemistry*; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D009842:Oligopeptides / Q000737:chemistry; D010446:Peptide Fragments / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D012694:Serine; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013329:Structure-Activity Relationship; D013388:Succinimides
D007202:Indicators and Reagents; D009842:Oligopeptides; D010446:Peptide Fragments; D010455:Peptides; D013388:Succinimides; D007987:Gonadotropin-Releasing Hormone; D012694:Serine; C022581:Bolton-Hunter reagent