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Engineered Fluorine Metabolism and Fluoropolymer Production in Living Cells
Author(s) -
Thuronyi B W.,
Privalsky Thomas M.,
Chang Michelle C. Y.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201706696
Subject(s) - fluorine , fluoropolymer , chemistry , bioplastic , synthetic biology , metabolic engineering , polyhydroxyalkanoates , molecule , yield (engineering) , metabolism , combinatorial chemistry , nanotechnology , organic chemistry , materials science , biochemistry , polymer , bacteria , enzyme , bioinformatics , biology , ecology , genetics , metallurgy
Fluorine has become an important element for the design of synthetic molecules for use in medicine, agriculture, and materials. Despite the many advantages provided by fluorine for tuning key molecular properties, it is rarely found in natural metabolism. We seek to expand the molecular space available for discovery through the development of new biosynthetic strategies that cross synthetic with natural compounds. Towards this goal, we engineered a microbial host for organofluorine metabolism and show that we can achieve the production of the fluorinated diketide 2‐fluoro‐3‐hydroxybutyrate at approximately 50 % yield. This fluorinated diketide can be used as a monomer in vivo to produce fluorinated poly(hydroxyalkanoate) (PHA) bioplastics with fluorine substitutions ranging from around 5–15 %. This system provides a platform to produce m m flux through the key fluoromalonyl coenzyme A (CoA) building block, thereby offering the potential to generate a broad range of fluorinated small‐molecule targets in living cells.