The enzyme participates in a pathway leading to biosynthesis of strigolactones, plant hormones involved in promotion of symbiotic associations known as arbuscular mycorrhiza.
mechanism of isomerization catalysed by OsD27 involving a 1-electron transfer from the polyene p-system of beta-carotene to a [2Fe2S] cluster, generating a radical cation, which is able to rotate about the C-C single bond. Electron transfer back from the reduced [2Fe2S] cluster then generates the 9-cis-beta-carotene product. A mechanism involving single electron transfer from a [2Fe2S] cluster to form a radical anion intermediate is also possible. OsD27 retains catalytic activity under anaerobic conditions, therefore it does not require dioxygen for activity
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SYSTEMATIC NAME
IUBMB Comments
beta-carotene 9-cis-all-trans isomerase
The enzyme participates in a pathway leading to biosynthesis of strigolactones, plant hormones involved in promotion of symbiotic associations known as arbuscular mycorrhiza.
catalytic mechanism involves a 1-electron transfer from the polyene pi-system of beta-carotene to a [2Fe-2S] cluster, generating a radical cation, which is able to rotate about the C-C single bond. Electron transfer back from the reduced [2Fe-2S] cluster would then generate the 9-cis-beta-carotene product. A mechanism involving single electron transfer from a [2Fe-2S] cluster to form a radical anion intermediate is also possible
the enzyme is strictly double bond-specific, solely targeting the C9-C10 double bond. DWARF27 does not introduce a 9-cis-double bond in 13-cis- or 15-cis-beta-carotene. Substrates are bicyclic carotenoids, including beta-, alpha-carotene and beta,beta-cryptoxanthin, that contain at least one unsubstituted beta-ionone ring
enzyme is not inhibited by hydroxamic acids that cause shoot branching in planta, but D27 is partially inhibited by terpene-like hydroxamic acids; OsD27 is not inhibited by hydroxamic acids that cause shoot branching in planta, but OsD27 is partially inhibited by terpene-like hydroxamic acids. Compounds D2, D4, D5 and D6 that show a shoot branching phenotype in planta give no inhibition at all. No inhibition by N-benzyl-N-hydroxy-2-(4-hydroxyphenyl)acetamide, N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-hydroxyphenyl)acetamide, N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-methoxyphenyl)acetamide, N-benzyl-2-(3,4-dimethoxyphenyl)-N-hydroxyacetamide, 2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide, 2-(2H-1,3-benzodioxol-5-yl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide, N-benzyl-N-hydroxy-3-(4-methoxyphenyl)propanamide, N-[(4-fluorophenyl)methyl]-N-hydroxy-3-(4-methoxyphenyl)propanamide, 3-(3,4-dimethoxyphenyl)-N-hydroxy-N-octylpropanamide, N-hydroxy-3-(4-methoxyphenyl)-N-octylpropanamide, (2E)-3-(3,4-dimethoxyphenyl)-N-hydroxyprop-2-enamide, 3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide, (2E)-N-hydroxy-3-(4-methoxyphenyl)prop-2-enamide, N-hydroxy-3-(4-methoxyphenyl)propanamide, (2E,4E)-N-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienamide, and abamine
biosynthesis pathway of strigolactones begins with the isomerization of all-trans-beta-carotene to 9-cis-beta-carotene catalysed by Dwarf27 (D27), strigolactone biosynthesis pathway from all-trans-beta-carotene to ent-2'-epi-5-deoxystrigol, overview
the enzyme is required for the regulation of axillary branching and the inhibition of secondary bud outgrowth. The enzyme is involved in strigolactone-mediated repression of shoot branching
biosynthesis of strigolactones requires the action of enzyme Dwarf27, which catalyzes the isomerization of all-trans-beta-carotene to 9-cis-beta-carotene
D27 is involved in strigolactone biosynthesis in roots upon phosphate stress. The gene is also highly expressed in nodule primordia and subsequently becomes restricted to the meristem and distal infection zone of a mature nodules
Biochemical characterization and selective inhibition of beta-carotene cis-trans isomerase D27 and carotenoid cleavage dioxygenase CCD8 on the strigolactone biosynthetic pathway
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5.2.1.14 beta-carotene isomerase
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