Date

Monday 03 Mar 2025

Time

15:15 - 15:45

Location

DM.1.15

Supervisor

Jeroen Codee

2nd reviewer

Dmitri Filippov

Jury

Steffen Brünle

Legionaminic and Acinetaminic acid are important bacterial carbohydrates that have been found in the CPS of MDR A. Baumannii. Although the CPS is pivotal for the virulence and the survivability of the bacteria, the precise role and functions of these nonulosonic acids are still unclear. Thus, a synthetic, large-scale route for nonulosonic analogues could be key in the development of new therapeutics, such as glycoconjugate vaccines. The goal of this project is to develop a synthetic method for both Legionaminic and 8-epi-Acinetaminic acid analogues starting from neuraminic acid, which can be utilised in the synthesis of a variety of different K-unit structures. Chapter 2 will focus describe the synthesis of both thioglycoside donors that feature C4 and C8 hydroxyl orthogonality. The selective deprotection and glycosylation of C4 and C8 allow this building block to be used for a large variety of K-units and other bacterial structures. Chapter 3 will investigate the reactivity and selectivity upon sialylation of the donor at the anomeric carbon.