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Enzymatic Synthesis and Characterization of L-Methionine and 2-Hydroxy-4-(methylthio)butanoic Acid (HMB) Co-oligomers
Journal of Agricultural and Food Chemistry
  • Mathur Rajesh
  • Shubhender Kapila, Missouri University of Science and Technology
  • Paul Ki-souk Nam, Missouri University of Science and Technology
  • Daniel Forciniti, Missouri University of Science and Technology
  • Stephen Lorbert
  • Charles Schasteen
Abstract

Oligomers of l-methionine (Met) and its hydroxy analogue, 2-hydroxy-4-(methylthio)butanoic acid (d,l-HMB) were synthesized with the proteolytic enzyme papain. The Met homooligomers and HMB−Met co-oligomers obtained through the enzymatic reactions were subjected to persulfonation and separated with reverse phase liquid chromatography (RPLC). The separated oligomers were characterized with electrospray ionization-mass spectrometry (ESI-MS). The oligomers were also characterized with matrix-assisted laser desorption ionization time of flight mass spectrometry (MALDI-TOF-MS). The results showed that co-oligomers were predominantly composed of 4−8 Met residues and one HMB residue. The data also suggest that in the co-oligomers, HMB is attached at the N-terminal end of the oligopeptide chain.

Department(s)
Chemistry
Second Department
Chemical and Biochemical Engineering
Keywords and Phrases
  • 2 Hydroxy 4 (Methylthio)butanoic Acid,
  • Butyric Acid Derivative,
  • Methionine,
  • Oligomer,
  • Papain,
  • Unclassified Drug,
  • article,
  • Enzyme Mechanism,
  • Mass Spectrometry,
  • Matrix Assisted Laser Desorption Ionization Time of Flight Mass Spectrometry,
  • Peptide Analysis,
  • Peptide Synthesis,
  • Protein Structure,
  • Reversed Phase Liquid Chromatography,
  • Chromatography, High Pressure Liquid,
  • Mass Spectrometry,
  • Methionine,
  • Papain,
  • HMB,
  • Methionine,
  • Methionine Hydroxy Analogue,
  • MHA,
  • Oligopeptides,
  • Methionine,
  • Oligopeptides
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2003 American Chemical Society (ACS), All rights reserved.
Publication Date
4-1-2003
Publication Date
01 Apr 2003
Citation Information
Mathur Rajesh, Shubhender Kapila, Paul Ki-souk Nam, Daniel Forciniti, et al.. "Enzymatic Synthesis and Characterization of L-Methionine and 2-Hydroxy-4-(methylthio)butanoic Acid (HMB) Co-oligomers" Journal of Agricultural and Food Chemistry Vol. 51 Iss. 9 (2003) p. 2461 - 2467 ISSN: 0021-8561
Available at: http://works.bepress.com/daniel-forciniti/13/