223449-25-0Relevant academic research and scientific papers
Efficient synthesis of water-soluble, phosphonate-terminated polyester dendrimers
Salamończyk, Grzegorz M.
, p. 7161 - 7164 (2015/12/12)
Simple and effective syntheses of novel, water-soluble, phosphonate-terminated polyester dendrimers varying in size and structure are described. These macromolecular compounds, consisting of thiophosphoric and 1,3,5-benzenetricarboxylic ester building blocks may find potential applications in health sciences as microbicides and/or as useful macromolecular models for functional coatings of superparamagnetic iron oxides (SPIOs) nanoparticles intended for use in hyperthermal therapy and magnetic resonance imaging (MRI). The dendrimers, possessing free phosphonate functional groups on the surface, were prepared in high yields from previously synthesized phosphorus-based substrates with 3,5-bis(dimethoxyphosphonyl)-methyl]benzoic acid (4), being an essential precursor of the dendrimer polyanionic surface. In addition, an interesting example of virtual coupling between remote nuclei in the 13C NMR spectrum of bisphosphonate monomer 3 was observed.
Optimization of a synthetic arginine receptor. Systematic tuning of noncovalent interactions
Rensing,Arendt,Springer,Grawe,Schrader
, p. 5814 - 5821 (2007/10/03)
The simple arginine binder 1 could be optimized by strengthening π-cation as well as electrostatic interactions. Electron-donating or -withdrawing substituents in the 5-position provide experimental evidence for π-cation interactions, because binding energies increase by up to 0.6 kcal/mol due to a single benzene-guanidinium interaction. Even more effective is the introduction of a third phosphonate functionality at the correct distance, so that the guanidinium cation is recognized by optimal electrostatic and hydrogen bond interactions. Monte Carlo simulations and NOESY experiments confirm the expected complex geometries. The optimized host molecule 8 binds arginine half an order of magnitude more efficiently than the parent molecule.
Synthesis of 3,5-bis(phosphonomethyl)benzoic acid and its application as a metal oxide surface bivalent anchor
Nakhle, Bassam M.,Trammell, Scott A.,Sigel, Keith M.,Meyer, Thomas J.,Erickson, Bruce W.
, p. 2835 - 2846 (2007/10/03)
A protected form of 3,5-bis(phosphonomethyl)benzoic acid (Bpb-OH), a metal oxide surface bivalent anchor, has been synthesized, coupled to an amine functionality, deprotected, and shown to bind to metal oxide surfaces. The protected anchor, 3,5-bis(dimethoxyphosphinylmethyl)benzoic acid (Me4Bpb-OH) was synthesized in 23% yield over four steps, coupled to a proline-chromophore, deprotected with a solution of iodotrimethylsilane (TMSI) in acetonitrile and adsorbed to Tin(IV)-doped indium oxide and nanocrystalline TiO2 electrodes at surface coverages of 1.5 x 10-10 mol cm-2 and 4.9 x 10-11 mol cm-2, respectively. Finally, Me4Bpb-OH was converted to an amino derivative by attaching a diamino butane linker.
