A deacetylation method based on lysine-assisted methanolysis of esters was developed. Existing methodologies entail the use of acids or bases, and sometimes high temperatures; conditions that can be detrimental to the more chemically unstable scaffolds. The present methodology complements and innovates on the well-established deacetylation techniques, as deprotection is achieved using a minimum molar equivalency of methanol and lysine under mild heating conditions, yielding the release of volatile methyl ester as a by-product. This method has been optimized to deacetylate a variety of canonical nucleosides and hydrolytically labile non-canonical nucleosides like nicotinamide riboside (NR) and its reduced form- dihydronicotinamide riboside (NRH), demonstrating its potential for nutraceutical and pharmacological applications. In addition, as a one-pot process and given the nutraceutical properties of lysine, the resulting lysine and nucleosides mixtures can generate valuable formulations.

Deacetylation of nucleosides by lysine assisted methanolysis of esters and amides

Fall 2022 abstracts, posters, and presentations will launch in mid-September.

ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.