Metabolic Conversion of Fluorenone Oxime to Phenanthridinone by Hepatic Enzymes

Golander, Yechiel; Sternson, Larry A.

doi:10.1002/jps.2600680708

Cited by 3 publications

(1 citation statement)

References 14 publications

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“…2B). It is known from animal systems that oximes can be converted to amides by a Beckmann-rearrangement-type enzymatic reaction requiring NADPH (31). Therefore, a similar enzymatic reaction might be involved in the formation of IAM from IAOx in Arabidopsis.…”

Section: Biosynthesis Of Iaoxmentioning

confidence: 99%

Biochemical analyses of indole-3-acetaldoxime-dependent auxin biosynthesis in Arabidopsis

Sugawara

Hishiyama

Jikumaru

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

288

345

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Auxins are hormones that regulate many aspects of plant growth and development. The main plant auxin is indole-3-acetic acid (IAA), whose biosynthetic pathway is not fully understood. Indole-3-acetaldoxime (IAOx) has been proposed to be a key intermediate in the synthesis of IAA and several other indolic compounds. Genetic studies of IAA biosynthesis in Arabidopsis have suggested that 2 distinct pathways involving the CYP79B or YUCCA (YUC) genes may contribute to IAOx synthesis and that several pathways are also involved in the conversion of IAOx to IAA. Here we report the biochemical dissection of IAOx biosynthesis and metabolism in plants by analyzing IAA biosynthesis intermediates. We demonstrated that the majority of IAOx is produced by CYP79B genes in Arabidopsis because IAOx production was abolished in CYP79B-deficient mutants. IAOx was not detected from rice, maize, and tobacco, which do not have apparent CYP79B orthologues. IAOx levels were not significantly altered in the yuc1 yuc2 yuc4 yuc6 quadruple mutants, suggesting that the YUC gene family probably does not contribute to IAOx synthesis. We determined the pathway for conversion of IAOx to IAA by identifying 2 likely intermediates, indole-3-acetamide (IAM) and indole-3-acetonitrile (IAN), in Arabidopsis. When 13 C6-labeled IAOx was fed to CYP79B-deficient mutants, 13 C 6 atoms were efficiently incorporated to IAM, IAN, and IAA. This biochemical evidence indicates that IAOx-dependent IAA biosynthesis, which involves IAM and IAN as intermediates, is not a common but a species-specific pathway in plants; thus IAA biosynthesis may differ among plant species.indole-3-acetic acid ͉ plant hormone

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Section: Biosynthesis Of Iaoxmentioning

confidence: 99%