Intriguing cellular processing of a fluorinated amino acid during protein biosynthesis in Escherichia coli
Mark D Vaughan1, Zhengding Su1, Elisabeth Daub1
1Department of Chemistry, University of Waterloo, 200 University Avenue West, Waterloo, ON N2L 3G1 Canada. jhonek@uwaterloo.ca.
Abstract:
Bioincorporation of the methionine analogue S-(2-fluoroethyl)-l-homocysteine (l-MFE) into bacteriophage lysozyme overproduced in Escherichia coli results not only in the expected l-MFE incorporation but surprisingly substantial l-vinthionine incorporation into the labeled lysozymes. Synthetic l-vinthionine itself however is not activated by purified Escherichia coli methionyl-tRNA synthetase. The indirect preparation of vinthionine-containing proteins has the potential to be an alternate strategy to prepare vinyl thioether moieties for click chemistry applications on proteins.
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