Publicación Artículo científico (article).

Three-Component Stereoselective Enzymatic Synthesis of Amino-Diols and Amino-Polyols

Digital.CSIC. Repositorio Institucional del CSIC
Digital.CSIC. Repositorio Institucional del CSIC
  • Ford, Grayson J.
  • Swanson, Christopher R.
  • Bradshaw Allen, Ruth T.
  • Marshall, James R.
  • Mattey, Ashley P.
  • Turner, Nicholas J.
  • Clapés Saborit, Pere
  • Flitsch, Sabine L.
Amino-polyols represent attractive chemical building blocks but can be challenging to synthesize because of the high density of asymmetric functionalities and the need for extensive protecting-group strategies. Here we present a three-component strategy for the stereoselective enzymatic synthesis of amino-diols and amino-polyols using a diverse set of prochiral aldehydes, hydroxy ketones, and amines as starting materials. We were able to combine biocatalytic aldol reactions, using variants of d-fructose-6-phosphate aldolase (FSA), with reductive aminations catalyzed by IRED-259, identified from a metagenomic library. A two-step process, without the need for intermediate isolation, was developed to avoid cross-reactivity of the carbonyl components. Stereoselective formation of the 2R,3R,4R enantiomers of amino-polyols was observed and confirmed by X-ray crystallography., We kindly acknowledge financial support from the European Research Council (788231-ProgrES-ERC-2017-ADG to S.L.F.; BIO-H-BORROW to N.J.T.). J.R.M. acknowledges the Industrial Biotechnology Innovation Centre (IBioIC) and BBSRC funding through a CASE studentship with Prozomix Ltd. P.C. acknowledges financial support from the project RTI2018-094637-BI00 funded by MCIN/AEI/10.13039/501100011033 and by “ERDF A way of making Europe” and project PCI2018-092937 MCIN/AEI/10.13039/501100011033 cofunded by the UE under the ERACoBioTech Tralaminol (European Union’s Horizon 2020 research and innovation programme grant agreement no. 722361)., Peer reviewed

Digital.CSIC. Repositorio Institucional del CSIC

Digital.CSIC. Repositorio Institucional del CSIC
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Digital.CSIC. Repositorio Institucional del CSIC