The Hydrolysis of Phosphinates and Phosphonates: A Review

Abstract

Phosphinic and phosphonic acids are useful intermediates and biologically active compounds which may be prepared from their esters, phosphinates and phosphonates, respectively, by hydrolysis or dealkylation. The hydrolysis may take place both under acidic and basic conditions, but the C-O bond may also be cleaved by trimethylsilyl halides. The hydrolysis of P-esters is a challenging task because, in most cases, the optimized reaction conditions have not yet been explored. Despite the importance of the hydrolysis of P-esters, this field has not yet been fully surveyed. In order to fill this gap, examples of acidic and alkaline hydrolysis, as well as the dealkylation of phosphinates and phosphonates, are summarized in this review.

The characterization of Moraxella catarrhalis carried in the general population

“…For instance, the alkaline phosphatase (AlkP) family catalyse the hydrolysis of polyphosphates and phosphonates into antibacterial agents. Enzymes in this family are known to be involved in the biosynthesis of antibiotics such as streptomycin, bialaphos and mitomycin [51,52]. Furthermore, PhoX family phosphatases catalyse the hydrolysis of phosphomonoester to a phosphate [53], whilst membraneassociated phospholipid phosphatases have a similar function [54].…”

Synthesis, characterized, QSAR studies and molecular docking of some phosphonates as COVID-19 inhibitors

“…Research based on chemistry and biology greatly contributes to the production of bio-inhibitors. According to the electronic and structural properties of phosphonates such as the phosphorus-carbon stable covalent bond and their high potential in biology, Phosphonate chemistry can be introduced as a suitable candidate for the production of biomaterials [ [1] , [2] , [3] ]. Phosphonates have a wide range of application in radiopharmaceuticals [ 4 ], enzyme inactivators [ 5 ], HIV protease inhibitor [ 6 ], cardiovascular drugs [ 7 ], anti-parasitic drugs [ 8 ], and antiviral drug [ 9 ].…”

Stereoselective Synthesis of 1-C-Diethylphosphonomethyl and -difluoromethyl Iminosugars from Sugar Lactams

“…In contrast to the naturally occurring and hydrolyzable P−O bond, the strength of the P−C bond endows these synthetic surrogates with metabolic resistance to phosphatase hydrolysis. 18 Nevertheless, this area is still rather underexplored, and only a few examples of so-called 1-Cphosphonomethyl iminosugars have been reported so far (Figure 1). This includes six-membered derivatives 1a−d designed as α-D-Gal, 19 β-D-Man, 19 α-D-GlcNAc, 20 and α-L-Ido 21 analogues, respectively, five-membered compounds 22 such as 1e, and pseudodisaccharide 1f.…”

“…To mimic the pyrophosphate part of the natural substrate, incorporation of phosphonic acids as isosteric analogues in terms of geometry and polarity has been pursued. In contrast to the naturally occurring and hydrolyzable P–O bond, the strength of the P–C bond endows these synthetic surrogates with metabolic resistance to phosphatase hydrolysis . Nevertheless, this area is still rather underexplored, and only a few examples of so-called 1- C -phosphonomethyl iminosugars have been reported so far (Figure ).…”