Issue 16, 2024

Investigation on the substrate specificity and N-substitution tolerance of PseF in catalytic transformation of pseudaminic acids to CMP-Pse derivatives

Abstract

Pseudaminic acid (Pse) belongs to a class of bacterial non-2-ulosonic acids, and has been implicated in bacterial infection and immune evasion. Various Pse structures with diverse N-substitutions have been identified in pathogenic bacterial strains like Pseudomonas aeruginosa, Campylobacter jejuni, and Acinetobacter baumannii. In this study, we successfully synthesized three new Pse species, including Pse5Ac7Fo, Pse5Ac7(3RHb) and Pse7Fo5(3RHb) using chemical methods. Furthermore, we investigated the substrate specificity of cytidine 5′-monophosphate (CMP)-Pse synthetase (PseF), resulting in the production of N-modified CMP-Pse derivatives (CMP-Pses). It was found that PseF was promiscuous with the Pse substrate and could tolerate different modifications at the two nitrogen atoms. This study provides valuable insights into the incorporation of variable N-substitutions in the Pse biosynthetic pathway.

Graphical abstract: Investigation on the substrate specificity and N-substitution tolerance of PseF in catalytic transformation of pseudaminic acids to CMP-Pse derivatives

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Article information

Article type
Edge Article
Submitted
01 feb. 2024
Accepted
20 mar. 2024
First published
21 mar. 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 5950-5956

Investigation on the substrate specificity and N-substitution tolerance of PseF in catalytic transformation of pseudaminic acids to CMP-Pse derivatives

X. Guo, Y. C. Cheung, C. Li, H. Liu, P. Li, S. Chen and X. Li, Chem. Sci., 2024, 15, 5950 DOI: 10.1039/D4SC00758A

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