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Carbapenems as water soluble organocatalysts

Williams, Thomas L., Nödling, Alexander, Tsai, Yu-Hsuan and Luk, Louis Y. P. 2018. Carbapenems as water soluble organocatalysts. Wellcome Open Research 2018 (3) , 107. 10.12688/wellcomeopenres.14721.1

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Abstract

Background: Identification of organocatalysts functioning in aqueous environments will provide methods for more sustainable chemical transformations and allow tandem reactions with biocatalysts, like enzymes. Here we examine three water-soluble carbapenem antibiotics (meropenem, doripenem, and ertapenem) as secondary amine organocatalysts in aqueous environments. Methods: The Michael addition of nitromethane to cinnamaldehyde was used as the model reaction. The reactions were monitored by 1H NMR, and the enantioselectivity was determined by chiral HPLC. Results: The effects of buffer components, pH, organic co-solvents and anchoring into a protein scaffold were investigated. Moderate yields of the Michael addition were obtained in buffer alone. The use of methanol as a co-solvent in a ratio of 1:1 increases the yield by 50%. Anchoring of the catalysts into a protein backbone reverses the enatioselectivity of the reaction. Conclusions: Despite only moderate yields and enantioselectivities being obtained, this study lays the foundations for future development of efficient organocatalysis in aqueous environments.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: F1000Research
ISSN: 2398-502X
Date of First Compliant Deposit: 4 December 2018
Last Modified: 23 Jul 2019 10:05
URI: http://orca.cf.ac.uk/id/eprint/117364

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