α,α-Difluorophosphonohydroxamic Acid Derivatives among the Best Antibacterial Fosmidomycin Analogues

Three α,α-difluorophosphonate derivatives of fosmidomycin were synthesized from diethyl 1,1-difluorobut-3-enylphosphonate and were evaluated on Escherichia coli. Two of them are among the best 1-deoxy-d-xylulose 5-phosphate reductoisomerase inhibitors, with IC50 in the nM range, much better than fos...

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Published inMolecules (Basel, Switzerland) Vol. 26; no. 16; p. 5111
Main Authors Dreneau, Aurore, Krebs, Fanny S., Munier, Mathilde, Ngov, Chheng, Tritsch, Denis, Lièvremont, Didier, Rohmer, Michel, Grosdemange-Billiard, Catherine
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 23.08.2021
MDPI
Subjects
1-deoxy- d xylulose 5-phosphate reductoisomerase (DXR)
Acids
Antibiotics
Antiinfectives and antibacterials
antimicrobial
Antimicrobial activity
Antimicrobial agents
Atmospheric pressure
Bacteria
Chemical Sciences
D-Xylulose 5-phosphate
deoxyxylulose phosphate reductoisomerase
E coli
Enzymes
Escherichia coli
Fluorine
Fosmidomycin
Gram-positive bacteria
isoprenoid biosynthesis
Nosocomial infections
Other
Phosphates
Phosphonates
Reductoisomerase
Xylulose
α,α-difluorophosphonate
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Summary:Three α,α-difluorophosphonate derivatives of fosmidomycin were synthesized from diethyl 1,1-difluorobut-3-enylphosphonate and were evaluated on Escherichia coli. Two of them are among the best 1-deoxy-d-xylulose 5-phosphate reductoisomerase inhibitors, with IC50 in the nM range, much better than fosmidomycin, the reference compound. They also showed an enhanced antimicrobial activity against E. coli on Petri dishes in comparison with the corresponding phosphates and the non-fluorinated phosphonate.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules26165111