Douglas Masterson

Associate Professor and Associate Chair

Organic/Bioorganic Chemistry

Website: http://www.usm.edu/masterson

Education:

  • B.S Chemistry; The University of Arkansas (1995)
  • Ph.D. Organic; The University of Oklahoma (1999)
  • Post doc.; Vanderbilt University (2000-2003)

Research Interests:

  • Enzymes in Organic Synthesis
  • Unnatural Amino Acid Syntheses
  • Mass Spectrometry
  • Free Radical Chemistry

Current Research:

Our research focuses on developing synthetic methodologies which exploit enzymes as catalysts to provide the chiral building blocks needed to construct unnatural amino acids, mass spectrometry, and free radical-promoted reactions.

  • Synthesis of unnatural amino acids using enzymatic processes
  • Incorporation of unnatural amino acids into biologically active peptides (e.g. Somatostatin-14) in order to improve biological activities and improve resistance toward proteolytic degradation
  • Developing reagents to modify proteins and peptides at specific residues which can promote the selective fragmentation of the protein/peptide at the modified residue location.
  • Synthesis of 15N-labeled compounds by a novel free radicalazidation process

Selected Publications:

  1. Almary Chacon, Douglas S. Masterson, Huiyong Yin, Daniel C. Liebler, and Ned A. Porter, “N-Terminal Amino Acid Side-Chain Cleavage of Chemically Modified Peptides in the Gas Phase: A Mass Spectrometry Technique for N-Terminus Identification.” Bioorganic & Medicinal Chemistry 2006, 14, 6213-6222.
  2. Douglas S. Masterson and Ned A. Porter, “Mechanism of β-Silyl Diacyl Peroxide Decomposition: A Mild and Stereoselective Synthesis of β-Silyl Esters.” The Journal of Organic Chemistry 2004, 69, 3693-3699.
  3. Douglas S. Masterson, Huiyong Yin, Almary Chacon, David L. Hachey, Jeremy L. Norris, and Ned A. Porter, “Lysine Peroxycarbamates: Free Radical-Promoted Peptide Cleavage.” Journal of the American Chemical Society 2004, 126, 720-721.
  4. Douglas S. Masterson and Ned A. Porter, “Diastereoselective Free Radical Halogenation, Azidation, and Thiopyridyl Rearrangement of β-Silyl Barton-Esters.” Organic Letters
    2002, 4, 4253-4256.