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Structure-Activity Relationship of Fluorinated Sialic Acid Inhibitors for Bacterial Sialylation.


ABSTRACT: Bacterial pathogens such as Nontypeable Haemophilus influenzae (NTHi) can evade the immune system by taking up and presenting host-derived sialic acids. Herein, we report a detailed structure-activity relationship of sialic acid-based inhibitors that prevent the transfer of host sialic acids to NTHi. We report the synthesis and biological evaluation of C-5, C-8, and C-9 derivatives of the parent compound 3-fluorosialic acid (SiaNFAc). Small modifications are tolerated at the C-5 and C-9 positions, while the C-8 position does not allow for modification. These structure-activity relationships define the chemical space available to develop selective bacterial sialylation inhibitors.

SUBMITTER: Moons SJ 

PROVIDER: S-EPMC8382218 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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Structure-Activity Relationship of Fluorinated Sialic Acid Inhibitors for Bacterial Sialylation.

Moons Sam J SJ   Rossing Emiel E   Heming Jurriaan J A JJA   Janssen Mathilde A C H MACH   van Scherpenzeel Monique M   Lefeber Dirk J DJ   de Jonge Marien I MI   Langereis Jeroen D JD   Boltje Thomas J TJ  

Bioconjugate chemistry 20210527 6


Bacterial pathogens such as Nontypeable <i>Haemophilus influenzae</i> (NTHi) can evade the immune system by taking up and presenting host-derived sialic acids. Herein, we report a detailed structure-activity relationship of sialic acid-based inhibitors that prevent the transfer of host sialic acids to NTHi. We report the synthesis and biological evaluation of C-5, C-8, and C-9 derivatives of the parent compound 3-fluorosialic acid (SiaNFAc). Small modifications are tolerated at the C-5 and C-9 p  ...[more]

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