Biosynthesis and Stability of Coiled-Coil Peptides Containing (2S,4R)-5,5,5-Trifluoroleucine and (2S,4S)-5,5,5-Trifluoroleucine
Jin Kim Montclare Prof.
Department of Chemical and Biological Sciences, Polytechnic University, Department of Biochemistry, SUNY Downstate Medical Center, Brooklyn, NY 11203 (USA)
These authors contributed equally to this work.
Search for more papers by this authorSoojin Son Dr.
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA), Fax: (+1) 626-793-8472
These authors contributed equally to this work.
Search for more papers by this authorGinevra A. Clark
Department of Chemistry, Tufts University, Medford, MA 02155 (USA)
Search for more papers by this authorKrishna Kumar Prof.
Department of Chemistry, Tufts University, Medford, MA 02155 (USA)
Cancer Center, Tufts-New England Medical Center, Boston, MA 02110 (USA)
Search for more papers by this authorDavid A. Tirrell Prof.
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA), Fax: (+1) 626-793-8472
Search for more papers by this authorJin Kim Montclare Prof.
Department of Chemical and Biological Sciences, Polytechnic University, Department of Biochemistry, SUNY Downstate Medical Center, Brooklyn, NY 11203 (USA)
These authors contributed equally to this work.
Search for more papers by this authorSoojin Son Dr.
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA), Fax: (+1) 626-793-8472
These authors contributed equally to this work.
Search for more papers by this authorGinevra A. Clark
Department of Chemistry, Tufts University, Medford, MA 02155 (USA)
Search for more papers by this authorKrishna Kumar Prof.
Department of Chemistry, Tufts University, Medford, MA 02155 (USA)
Cancer Center, Tufts-New England Medical Center, Boston, MA 02110 (USA)
Search for more papers by this authorDavid A. Tirrell Prof.
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA), Fax: (+1) 626-793-8472
Search for more papers by this authorGraphical Abstract
Life in stereo: We report the effects of 5,5,5-trifluoroleucine (TFL) stereochemistry on coiled-coil peptide biosynthesis and stability. We demonstrate that two diastereoisomers of TFL are activated and incorporated into peptides expressed in E. coli. Coiled-coil homodimers of these peptides exhibited increased stability. An equimolar mixture of the two fluorinated peptides formed a heterodimer of modestly enhanced thermal stability relative to the homodimers (see figure).
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