Identification and Characterization of O-Biotinylated Hydroxy Amino Acid Residues in Peptides

B. T. Miller, M. E. Rogers, J. S. Smith, A. Kurosky

    Research output: Contribution to journalArticle

    17 Citations (Scopus)

    Abstract

    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.

    Original languageEnglish (US)
    Pages (from-to)240-248
    Number of pages9
    JournalAnalytical Biochemistry
    Volume219
    Issue number2
    DOIs
    StatePublished - Jun 1994

    Fingerprint

    Hydroxy Acids
    Biotin
    Amino Acids
    Peptides
    Esters
    Aminocaproic Acid
    Protein Sequence Analysis
    Proteolysis
    Hydroxyl Radical
    Chemical reactivity
    Sequence Analysis
    Derivatives
    Degradation
    Proteins
    N-hydroxysuccinimide

    ASJC Scopus subject areas

    • Molecular Biology
    • Biophysics
    • Biochemistry

    Cite this

    Identification and Characterization of O-Biotinylated Hydroxy Amino Acid Residues in Peptides. / Miller, B. T.; Rogers, M. E.; Smith, J. S.; Kurosky, A.

    In: Analytical Biochemistry, Vol. 219, No. 2, 06.1994, p. 240-248.

    Research output: Contribution to journalArticle

    Miller, B. T. ; Rogers, M. E. ; Smith, J. S. ; Kurosky, A. / Identification and Characterization of O-Biotinylated Hydroxy Amino Acid Residues in Peptides. In: Analytical Biochemistry. 1994 ; Vol. 219, No. 2. pp. 240-248.
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