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Biosynthesis and Stability of Coiled‐Coil Peptides Containing (2 S ,4 R )‐5,5,5‐Trifluoroleucine and (2 S ,4 S )‐5,5,5‐Trifluoroleucine
Author(s) -
Montclare Jin Kim,
Son Soojin,
Clark Ginevra A.,
Kumar Krishna,
Tirrell David A.
Publication year - 2009
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200800164
Subject(s) - coiled coil , diastereomer , biosynthesis , peptide , thermal stability , chemistry , stereochemistry , combinatorial chemistry , biochemistry , gene , organic chemistry
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).