The oxidative deamination of <i>N</i>-acetyl neuraminic acid gives easy access to a number of C5 derivates of the sialic acids with potentially interesting biological activity. We now report the extension of our studies in this area to encompass the use of phenols and thiophenols as nucleophiles. In addition to the anticipated direct substitution products, a variety of previously unknown products with novel structures arising from the formation and trapping of an intermediate vinyl diazonium ion will be described. These structurally novel sialic acid derivates potentially open the way to the development of a new class of sialidase inhibitors.

Phenols as nucleophiles in the oxidative deamination of <i>N-</i>acetyl neuraminic acid

2019 Fall National Meeting

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

Phenols as nucleophiles in the oxidative deamination of N-acetyl neuraminic acid