Identification and characterization of O-biotinylated hydroxy amino acid residues in peptides

Analytical Biochemistry
B T MillerA Kurosky


Recent findings have indicated that certain hydroxyl groups of peptides have enhanced intrinsic chemical reactivity and can be O-acylated by N-hydroxysuccinimide esters of biotin. Analytical procedures are described for the identification of O-acylated derivatives of seryl, threonyl, and tyrosyl residues after reaction with the N-hydroxysuccinimide ester of biotin containing the extended spacer arm 6-aminohexanoic acid. The identification and chemical characterization of O-biotinylated residues included amino acid analysis, peptide sequence determination, and mass spectrometric analysis. The application of these analytical procedures provided unequivocal identification of O-biotinylated residues for a number of peptides investigated. In a separate study, we also show that O-biotinylated amino-terminal seryl residues occurring after proteolysis of peptides or proteins can rapidly undergo an O-->N acyl shift resulting in blockage of sequence analysis by the Edman degradation procedure.


Jul 3, 2013·AAPS PharmSciTech·Luiz Henrique GuerreiroLuís Maurício T R Lima
Feb 11, 1998·Journal of Biomedical Materials Research·D L Hern, J A Hubbell
Jan 22, 2011·Electrophoresis·Benjamin RogersRichard D Oleschuk
Nov 16, 2007·Journal of Proteome Research·Nicolas AbelloRainer Bischoff

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