The Synthesis of Enantiopure α-Fluoro and α,α-Difluoro-β3-Arginine Derivatives

AUSTRALIAN JOURNAL OF CHEMISTRY(2014)

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摘要
The synthesis of a set of monofluorinated, difluorinated, and non-fluorinated N-acetylated-beta(3)-arginine esters, potential inhibitors of trypsin-like proteases, is described. Elaboration to the target compounds from previously reported enantiopure precursors derived from 3-hydroxypropanal involved 6-7 steps and was achieved in 48-65% overall yield. The alpha,alpha-difluoro-beta(3)-arginine derivative was found to be particularly prone to hydrolysis. Three beta(3)-arginine derivatives were tested for their ability to inhibit trypsin, the alpha,alpha-difluoro compound being assayed in the form of a carboxylate zwitterion.
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colloids,crystallography,medicinal chemistry,self assembly,mass spectrometry,green chemistry,supramolecular chemistry,combinatorial chemistry,pharmaceutical chemistry,ionic liquids,amino acids,density functional theory,structure,educational,physical chemistry,quantum chemistry,peptide,reaction mechanisms,analytical chemistry,biocatalysis,crystal structures,sensors,combinatorial,computational chemistry,spectroscopy,biological chemistry,kinetics,inorganic chemistry,organic chemistry,biosensors,catalysis,electrochemistry,nanotechnology,proteins,interfaces,polymer chemistry,photochemistry,enzymes,macromolecules,ab initio calculations,surface chemistry
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