The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2-((1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethanol( cas:35836-73-8 ) is researched.Product Details of 35836-73-8.Graham, Brian J.; Windsor, Ian W.; Gold, Brian; Raines, Ronald T. published the article 《Boronic acid with high oxidative stability and utility in biological contexts》 about this compound( cas:35836-73-8 ) in ChemRxiv. Keywords: boronic acid oxidative stability crystal structure pharmacophore. Let’s learn more about this compound (cas:35836-73-8).
Despite their desirable attributes, boronic acids have had a minimal impact in biol. contexts. A significant problem has been their oxidative instability. At physiol. pH, phenylboronic acid and its boronate esters are oxidized by reactive oxygen species at rates comparable to those of thiols. After considering the mechanism and kinetics of the oxidation reaction, we reasoned that diminishing electron d. on boron could enhance oxidative stability. We found that a boralactone, in which a carboxyl group serves as an intramol. ligand for the boron, increases stability by 104-fold. Computational analyses revealed that the resistance to oxidation arises from diminished stabilization of the p orbital of boron that develops in the rate-limiting transition state of the oxidation reaction. Like simple boronic acids and boronate esters, a boralactone binds covalently and reversibly to 1,2-diols, such as those in saccharides. The kinetic stability of its complexes is, however, at least 20-fold greater. A boralactone also binds covalently to a serine side chain in a protein. These attributes confer unprecedented utility upon boralactones in the realms of chem. biol. and medicinal chem.
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Reference:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics