The NIH-shift in the in vivo hydroxylation of ring-deuterated L-phenylalanine in man

Archives of Biochemistry and Biophysics
W D Lehmann, H C Heinrich

Abstract

Oral loading with L-[ring-2H5]phenylalanine has been performed at a dose of 25 mg/kg for detection of heterozygotes for classic phenylketonuria. Using three differently labeled batches of ring-deuterated L-phenylalanine, quantitative analysis of deuterium-labeled L-phenylalanine and L-tyrosine in plasma revealed different label distributions. Three different reaction mechanisms for the 4-hydroxylation of L-phenylalanine to L-tyrosine were used as the basis for model calculations of the transformation of the L-phenylalanine label distribution into that of L-tyrosine. The best agreement between observed and calculated distributions was found for the mechanism involving a migration of the 4-substituent into the 3- or 5-position (NIH-shift), followed by a random loss of the 4-/3- or the 4-/5-substituent from this intermediate structure.

References

Apr 30, 1985·Clinica Chimica Acta; International Journal of Clinical Chemistry·W D Lehmann, H C Heinrich
Sep 8, 1966·Biochemical and Biophysical Research Communications·G GuroffJ Daly
Oct 20, 1966·Biochemical and Biophysical Research Communications·G GuroffS Udenfriend
Mar 27, 1984·Clinica Chimica Acta; International Journal of Clinical Chemistry·W D LehmannR Grüttner

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Citations

Mar 7, 2002·Journal of Agricultural and Food Chemistry·Wolfgang Engel

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