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Chemoenzymatic and Biocatalytic Synthesis of Aminodiols (BiCE Project)
This major EPSRC interdisciplinary research project set out to establish a systematic approach to achieving the integration of chemical, biocatalytic and bioprocess strategies for the synthesis of key chiral synthons. The project is in collaboration with Prof. G. J. Lye(Biochemical Engineering), Dr. J. M. Ward (Biochemistry), Dr. P. A. Dalby (Biochemical Engineering), Dr. F. Baganz (Biochemical Engineering), Dr M. Micheletti (Biochemical Engineering) Dr N. Szita (Biochemical Engineering) and Prof. J. M. Woodley(Chemical Engineering, DTU, Denmark). The synthesis of novel aminodiols is being investigated through the linkage of advanced biotransformations: C-C bond formation using transketolase (TK), reductive amination using transaminase (TAm), and molecular evolution techniques are being developed to enhance the component enzymes. The biocatalytic formation of acyclic α,α'-dihydroxyketones by TK is well documented in the literature, but in this project we have discovered a novel atom efficient one-pot synthesis of dihydroxyketones in water via a mimic of the transketolase reaction. The formation of a quaternary ammonium enolate is postulated in this tertiary-amine mediated carbon-carbon bond forming reaction. In order to identify TK mutants and active TAms the development of assays and chiral assays is crucial: we have recently identified a colorimetric assay for TK high throughput applications and the use of LC-MS is has been developed for high-throughput aminodiol screens. Chiral assays have also been developed for the α,α'-dihydroxy ketone products and using this new mutants generated that are able to generate either the (R)- or (S)- product in high e.e.s. Novel highly stereospecific ω-transaminases have also been identified that can convert α,α'-dihydroxyketones to aminodiols. Further studies include the use of TK and TAm in target molecule synthesis.
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