52178-61-7Relevant articles and documents
Synthesis and biological activities of a series of 4,5-diaryl-3-hydroxy-2(5H)-furanones
Bailly, Fabrice,Queffelec, Clemence,Mbemba, Gladys,Mouscadet, Jean-Francois,Pommery, Nicole,Pommery, Jean,Henichart, Jean-Pierre,Cotelle, Philippe
, p. 1222 - 1229 (2008/09/20)
A series of thirteen 4,5-diaryl-3-hydroxy-2(5H)-furanones were synthesized. They were evaluated for their antioxidant potencies and inhibitory properties of 5-lipoxygenase, cyclooxygenases, HIV-1 integrase and PC3 cell proliferation. New hits were discove
Mechanistic and stereochemical study of phenylpyruvate tautomerase
Pirrung, Michael C.,Chen, Jrlung,Rowley, Elizabeth G.,McPhail, Andrew T.
, p. 7103 - 7110 (2007/10/02)
A variety of substrates and potential enol/enolate mimics for the product/transition state of the enzyme phenylpyruvate tautomerase (E.C. 5.3.2.1) have been prepared and studied. Their stereostructures have been secured by a combination of NMR spectroscopy based on vicinal H-F and H-C coupling constants and X-ray crystallography. On the basis of the inhibition by stereoisomeric substituted cinnamates, it has been concluded that the enzyme produces the thermodynamically less stable (E) enol via a syn tautomerization transition state. Free energy profiles for the reaction suggest that vinyl fluorides act as product analogues. Because amide and dicarboxylate enolate mimics are relatively poor inhibitors of the enzyme, it is believed that an enolate is not involved in the tautomerization process.
Conversion of Phenolic α-Amino Acids into α-Keto Acids
Klein, Christian,Schulz, Guenter,Steglich, Wolfgang
, p. 1638 - 1639 (2007/10/02)
A one-pot conversion of tyrosine (1a) and 3,4-dihydroxyphenylalanine (DOPA) (1b) into 3-(4-hydroxyphenyl)pyruvic acid (2a) and 3-(3,4-dihydroxyphenyl)pyruvic acid (2b), respectively, via 2-trifluoromethyl-3-oxazolin-5-ones 5 is described.