Carbapenems as water soluble organocatalysts.

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

SUBMITTER: Williams TL 

PROVIDER: S-EPMC6198258 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature