The importance of phosphorus can be highlighted not only through its biological significance, but also in its many varied industrial, medicinal, and synthetic applications. Phosphonate moieties in particular have broad applications including their use as reagents in the Horner-Wadsworth-Emmons olefination reaction, a widely used synthetic strategy. As an alternative to the often harsh condition...

Semi-labile dissolved organic matter (DOM) accumulates in surface waters of the oligotrophic ocean gyres and turns over on seasonal to annual timescales. This reservoir of DOM represents an important source of carbon, energy, and nutrients to marine microbial communities but the identity of the microorganisms and the biochemical pathways underlying the cycling of DOM remain largely uncharacteri...

The enantioselective Friedel-Crafts addition of a variety of indoles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes (Sc(III)-pybox) was accomplished utilizing a series of beta-substituted alpha,beta-unsaturated phosphonates and alpha,beta-unsaturated 2-acyl imidazoles. The acyl phosphonate products were efficiently transformed into esters and amides, whereas the acyl imid...

Direct hydroxide attack on the scissile carbonyl of the substrate has been suggested as a likely mechanism for esterase antibodies elicited by phosphonate haptens, which mimic the transition states for the alkaline hydrolysis of esters.1 The unique amidase activity of esterase antibody 43C9 has been attributed to nucleophilic attack by an active-site histidine residue.2 Yet, the active site of ...

Previous published work has led to the hypothesis that the activatable esterase of chemotaxis is a serine esterase of the rabbit polymorphonuclear leukocyte existing in an inert, phosphonate insusceptible form, which after activation is capable of hydrolyzing aromatic amino acid esters and being inhibited by phosphonates. In the present study, directed to the testing of this hypothesis, we have...

In the oligotrophic ocean where inorganic phosphate (Pi) concentrations are low, microorganisms supplement their nutrient requirements with phosphorus (P) extracted from dissolved organic matter (DOM). Most P in DOM is bound as esters, which hydrolyzed by phosphoesterases to Pi. However, a large fraction of DOM-P occurs phosphonates, reduced organophosphorus compounds CP bond that do not yield...

Within this work, a modified preparation of diethyl 4-azidobenzylphosphonate (L1) is presented and the family 4- or 4′-azido-substituted aromatic phosphonate esters increased by three new ligand platforms: diisopropyl (L2), ((4′-azido-[1,1′-biphenyl]-4-yl)methyl)phosphonate (L3), 4-azido-2,3,5,6-tetrafluorobenzylphosphonate (L4), which exhibit an anomalous splitting N3 stretching vibrations. Su...

Owing to the attractiveness of organic phosphonic acids and esters in pharmacological field functionalization conductive metal-oxides, research effective synthetic protocols is pivotal. Among others, ?-bromoalkylphosphonates are gaining particular attention because they useful building blocks for tailored complex molecules. Hence, this work, optimization Michaelis–Arbuzov reaction conditions ha...