Incorporation of label from 13C-, 2H-, and 15N-labeled methionine molecules during the biosynthesis of 2′-deoxymugineic acid in roots of wheat

Jian Feng Ma, Kyosuke Nomoto

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The biosynthetic pathway of 2′-deoxymugineic acid, a key phytosiderophore, was investigated by feeding 13C-, 2H-, and 15N-labeled methionine, the first precursor, to the roots of hydroponically cultured wheat (Triticum aestivum L. cv Minori). The incorporation of label from each methionine species was observed during their conversion to 2′-deoxymugineic acid, using 2H-, 15N-, and 13C-nuclear magnetic resonance (NMR). L-[1-13C]Methionine (99% 13C) was efficiently incorporated, resulting in 13C enrichment of the three carboxyl groups of 2′-deoxymugineic acid. Use of D,L-[15N]methionine (95% 15N) resulted in 15N enrichment of 2′-deoxymugineic acid at the azetidine ring nitrogen and the secondary amino nitrogen. When D,L-[2,3,3-2H3-S-methyl-2H 3]methionine (98.2% 2H) was fed to the roots, 2H-NMR results indicated that only six deuterium atoms were incorporated, and that the deuterium atom from the C-2 position of each methionine was almost completely lost. [2,2,3,3-2H4]1-Aminocyclopropane-1-carboxylic acid (98% 2H) was not incorporated into 2′-deoxymugineic acid. These data and our previous findings demonstrated that only the deuterium atom from the C-2 position of L-methionine was lost, and that other atoms were completely incorporated when three molecules of methionine were converted to 2′-deoxymugineic acid. These observations are consistent with the conversion of L-methionine to azetidine-2-carboxylic acid, suggesting that L-methionine is first converted to azetidine-2-carboxylic acid during biosynthesis leading to 2′-deoxymugineic acid. Based on these results, a hypothetical pathway from L-methionine to 2′-deoxymugineic acid was postulated.

Original languageEnglish
Pages (from-to)607-610
Number of pages4
JournalPlant Physiology
Volume105
Issue number2
Publication statusPublished - Jun 1994
Externally publishedYes

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Methionine
Triticum
methionine
biosynthesis
wheat
acids
deuterium
Deuterium
Azetidinecarboxylic Acid
carboxylic acids
nuclear magnetic resonance spectroscopy
2'-deoxymugineic acid
Magnetic Resonance Spectroscopy
Nitrogen
phytosiderophores
amino nitrogen
1-aminocyclopropane-1-carboxylic acid
Biosynthetic Pathways
biochemical pathways
Triticum aestivum

ASJC Scopus subject areas

  • Plant Science

Cite this

Incorporation of label from 13C-, 2H-, and 15N-labeled methionine molecules during the biosynthesis of 2′-deoxymugineic acid in roots of wheat. / Ma, Jian Feng; Nomoto, Kyosuke.

In: Plant Physiology, Vol. 105, No. 2, 06.1994, p. 607-610.

Research output: Contribution to journalArticle

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abstract = "The biosynthetic pathway of 2′-deoxymugineic acid, a key phytosiderophore, was investigated by feeding 13C-, 2H-, and 15N-labeled methionine, the first precursor, to the roots of hydroponically cultured wheat (Triticum aestivum L. cv Minori). The incorporation of label from each methionine species was observed during their conversion to 2′-deoxymugineic acid, using 2H-, 15N-, and 13C-nuclear magnetic resonance (NMR). L-[1-13C]Methionine (99{\%} 13C) was efficiently incorporated, resulting in 13C enrichment of the three carboxyl groups of 2′-deoxymugineic acid. Use of D,L-[15N]methionine (95{\%} 15N) resulted in 15N enrichment of 2′-deoxymugineic acid at the azetidine ring nitrogen and the secondary amino nitrogen. When D,L-[2,3,3-2H3-S-methyl-2H 3]methionine (98.2{\%} 2H) was fed to the roots, 2H-NMR results indicated that only six deuterium atoms were incorporated, and that the deuterium atom from the C-2 position of each methionine was almost completely lost. [2,2,3,3-2H4]1-Aminocyclopropane-1-carboxylic acid (98{\%} 2H) was not incorporated into 2′-deoxymugineic acid. These data and our previous findings demonstrated that only the deuterium atom from the C-2 position of L-methionine was lost, and that other atoms were completely incorporated when three molecules of methionine were converted to 2′-deoxymugineic acid. These observations are consistent with the conversion of L-methionine to azetidine-2-carboxylic acid, suggesting that L-methionine is first converted to azetidine-2-carboxylic acid during biosynthesis leading to 2′-deoxymugineic acid. Based on these results, a hypothetical pathway from L-methionine to 2′-deoxymugineic acid was postulated.",
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