Phosphonate Analogues of Arabinose 5‐Phosphate: Putative Ligands for Arabinose 5‐Phosphate Isomerases

Gabrielli, Luca; Airoldi, Cristina; Sperandeo, Paola; Gianera, Serena; Polissi, Alessandra; Nicotra, Francesco; Cipolla, Laura

doi:10.1002/ejoc.201300887

Cited by 4 publications

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“…In 2013, Cipolla and co‐authors developed a series of arabinose 5‐phosphate (A5P) analogs bearing different phosphate mimetic group at the 5‐position ( 318 – 320 , Figure 24). [261] These analogs were obtained via the replacement of phosphate moiety by methylenephosphate, hydroxylmethylphosphate, and DFMP groups. The authors also tested theirs in vivo antibacterial activities against assorted Pseudomonas aeruginosa and Escherichia coli strains.…”

Section: Difluoromethylene Phosphonates Of Significant Biological Importancementioning

confidence: 99%

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Recent Advances in Synthesis of Difluoromethylene Phosphonates for Biological Applications

et al. 2021

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For almost 40 years, difluoromethylene phosphonates have proven to be versatile molecular tools in biochemical studies owing to their close resemblance to naturally occurring phosphates and phosphonates. As bioisosteric, non‐hydrolyzable analogs of these essential molecules, difluoromethylene phosphonates can target the critical parts of the cellular machinery and therefore exhibit a diverse spectrum of biological activity. In the past ten years, there have appeared many new methods for the synthesis of difluoromethylene phosphonates. Most notably, photoredox catalysis has firmly entered the field, while cross‐coupling and nucleophilic strategies have met considerable elaboration and refinement, entirely in accord with the current trends in synthetic organic chemistry. Herein, we introduce difluoromethylene phosphonates as a distinct, high‐tech subclass of synthetic phosphonates resulting from the research efforts on the cross‐section of organophosphorus, organofluorine, and bioorganic chemistry. We then proceed to the discussion of general methods for the preparation of difluoromethylene phosphonates, comprehensively reviewing reactions developed in the past 15 years while providing the context of earlier works where appropriate. Finally, we present selected examples of molecules with high biological activity, their biological targets, and the synthetic steps employed for their preparation.

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Section: Difluoromethylene Phosphonates Of Significant Biological Importancementioning

confidence: 99%

“…Removal of Bn group via treatment by Pd(OH) 2 in ethanol gave the compound 324 , which underwent hydrolysis affording the acid 325 . Finally, deprotection and treatment by sodium hydroxide afforded the desired DFMP‐containing analog 320 [261] …”

Section: Difluoromethylene Phosphonates Of Significant Biological Importancementioning

confidence: 99%

Recent Advances in Synthesis of Difluoromethylene Phosphonates for Biological Applications

et al. 2021

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Synthesis and Applications ofP–R_f‐Containing Molecules

Zhang

2020

Emerging Fluorinated Motifs

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