Mechanistic and stereochemical study of phenylpyruvate tautomerase

…, J Chen, EG Rowley, AT McPhail

Index: Pirrung, Michael C.; Chen, Jrlung; Rowley, Elizabeth G.; McPhail, Andrew T. Journal of the American Chemical Society, 1993 , vol. 115, # 16 p. 7103 - 7110

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Citation Number: 52

Abstract

Abstract: A variety of substrates and potential enol/enolate mimics for the product/transition state of the enzyme phenylpyruvate tautomerase (EC 5.3. 2.1) have been prepared and studied. Their stereostructures have been secured by a combination of NMR spectroscopy based on vicinal HF and HC coupling constants and X-ray crystallography. On the basis of the inhibition by stereoisomeric substituted cinnamates, it has been concluded that the ...