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Bio- & Photo-Catalytic Methods for the Construction of Enantiomerically Pure C-S Bonds in Thiols and Sulphides

Project description

Novel methods for the synthesis of chiral sulfur compounds

Chiral sulfur compounds are encountered in natural products, pharmaceutical ingredients such as penicillin as well as in flavours and fragrances. In the last case, their configuration endows them with specific olfactory properties. For their wide implementation in manufacturing processes, there is a need for sustainable methods to construct stereospecific C–S bonds. Scientists of the EU-funded BioPhoCS project will explore visible light photocatalysis and oxidoreductase enzymes to develop robust methods for the photo-biocatalytic synthesis of enantiomerically pure sulfur compounds. The successfully generated methods are expected to find application in the manufacturing of pharmaceutical ingredients, agrochemicals and fragrances.

Objective

Organic sulphur compounds containing C-S chiral centres represent one of the most intriguing classes of chemicals due to their peculiar properties conferred by the unique chemistry of sulphur. Chiral sulphur compounds are known for their olfactory properties as flavours and fragrances and are ubiquitous in natural products and pharmaceutical ingredients such as penicillins and verticillins. Both the flavouring and pharmaceutical properties of chiral sulphur compounds are often determined by their absolute configurations. Therefore, the development of novel, robust and sustainable methods for the enantioselective construction of C-S bonds is of great importance in chemistry. In view of the lack of efficient and stereoselective methods in assembling asymmetrical C-S bonds, within this project we aim to construct enantiopure sulphur compounds through photo- and bio-catalysis. Various strategies have been designed to achieve this target, exploiting blue/green light photocatalysis and biocatalysis by reductase enzymes such as KRED, ADH and ERED. The ability of these enzymes to biocatalyse the enantioselective reduction of thioketones and thioalkenes obtained via photocatalysis, will be investigated. In addition, the combination of photocatalytic synthesis of substrates with the biocatalytic construction of enantiomerically pure C-S bonds in one-pot cascade processes will be developed. These methods will be finally applied to the synthesis of chiral volatile sulphur compounds as odorous excipients, while in-situ NMR kinetic studies of the photo-biocatalytic reactions will be carried out to get a better understanding of the reaction mechanisms. The successful development of these strategies will allow chemists and industries to access facile and sustainable approaches to prepare a wide range of challenging chiral thiols and sulphides to be used in the manufacturing of pharmaceutical ingredients, fine chemical tools (ligands, catalysts), agrochemicals and fragrances.

Fields of science (EuroSciVoc)

Keywords

Programme(s)

Topic(s)

Funding Scheme

MSCA-IF - Marie Skłodowska-Curie Individual Fellowships (IF)

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Call for proposal

(opens in new window) H2020-MSCA-IF-2018

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Coordinator

UNIVERSITY COLLEGE LONDON
Net EU contribution
€ 131 211,36
Address
GOWER STREET
WC1E 6BT London
United Kingdom
Region
London Inner London — West Camden and City of London
Activity type
Higher or Secondary Education Establishments
Links
Total cost
€ 131 211,36

Participants (1)