PMID: 11607147Jan 15, 1991Paper

2-nitro-3-(p-hydroxyphenyl)propionate and aci-1-nitro-2-(p-hydroxyphenyl)ethane, two intermediates in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench

Proceedings of the National Academy of Sciences of the United States of America
B A HalkierBirger Lindberg Møller

Abstract

The biosynthetic pathway for the cyanogenic glucoside dhurrin derived from tyrosine has been studied in vitro by using [18O]oxygen and a microsomal enzyme system obtained from etiolated sorghum seedlings. The products formed were purified by HPLC and TLC, and the incorporation of [18O]oxygen was monitored by mass spectrometry. In the presence of NADPH and [18O]dioxygen, L-tyrosine is converted to (E)- and (Z)-p-hydroxyphenylacetaldehyde oxime with quantitative incorporation of an [18O]oxygen atom into the oxime function. The first step in this conversion is the N-hydroxylation of L-tyrosine to N-hydroxytyrosine. Administration of N-hydroxytyrosine as a substrate results in the production of 1-nitro-2-(p-hydroxyphenyl)ethane in addition to (E)- and (Z)-p-hydroxyphenylacetaldehyde oxime, with quantitative incorporation of a single [18O]oxygen atom in all three products. These data demonstrate that the conversion of N-hydroxytyrosine to p-hydroxyphenylacetaldehyde oxime involves additional N-hydroxylation and N-oxidation reactions giving rise to the formation of 2-nitro-3-(p-hydroxyphenyl)propionate, which by decarboxylation produces aci-1-nitro-2-(p-hydroxyphenyl)ethane. Both compounds are additional intermediates in the pathway....Continue Reading

Citations

Sep 13, 2015·The Plant Journal : for Cell and Molecular Biology·Mette ClausenBirger Lindberg Møller
Jan 1, 1992·Archives of Biochemistry and Biophysics·B KochB L Møller
Nov 26, 2009·Phytochemistry·Kenneth Jensen, Birger Lindberg Møller
Apr 17, 2013·Biotechnology and Applied Biochemistry·Tomas LaursenBirger Lindberg Møller
Jul 24, 2018·The Plant Journal : for Cell and Molecular Biology·Michael Hartmann, Jürgen Zeier
Sep 13, 2020·Communications Biology·Sara ThodbergElizabeth Heather Jakobsen Neilson
Aug 1, 1994·The New Phytologist·Richard N Bennett, Roger M Wallsgrove
Jul 23, 1999·Archives of Biochemistry and Biophysics·J S Nielsen, B L Moller

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