Synthesis of microbial sialic acids for the study of their glycobiology

Session: 
S7.4 Tools to study sialic acid type glycans
Code: 
OL7.4.1
Location (hall): 
Fucose
Start/end time: 
Wednesday, July 3, 2019 - 11:45 to 12:00
Xianke
Meng

Xianke Meng1, Tom Wennekes1, Geert-Jan Boons1

1Department of Chemical Biology and Drug Discovery, Bijvoet Center for Biomolecular Research, and Utrecht Institute for Pharmaceutical Sciences, Utrecht University, Utrecht, The Netherlands

Pseudaminic acid (Pse) and Legionaminic acid (Leg) are nine-carbon diamino α-ketone monosaccharides that are found as important terminal components of cell surface glycoconjugates in various human-associated microbes such as C. jejuni and M. smithii. However, the exact biological roles of Pse and Leg are not yet fully understood and research in this area is constrained by the difficulties in obtaining Pse and Leg. To further explore their glycobiological significance, we have developed a robust synthesis route for Pse and its derivatives that allows for modifications to create molecular probe derivatives that will allow investigation of its microbial glycobiology. Moreover, we also modified a previously reported synthesis of Leg[1] to create probes that allow for metabolic labeling of Leg.

The synthesis overview of Pseudaminic acid and Legionaminic acid.

References: 
  1. Santra, A.; Xiao, A.; Yu, H.; li, W.; Li, Y.; Ngo, N.; McArthur, J. B.; Chen, X. Angew. Chem., Int. Ed. 2018, 57, 2929– 2933.

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