Enzymes
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- Name help_outline 1-O-(indol-3-ylacetyl)-β-D-glucose Identifier CHEBI:17990 (Beilstein: 496559; CAS: 19817-95-9) help_outline Charge 0 Formula C16H19NO7 InChIKeyhelp_outline HHDMMUWDSFASNB-JZYAIQKZSA-N SMILEShelp_outline OC[C@H]1O[C@@H](OC(=O)Cc2c[nH]c3ccccc23)[C@H](O)[C@@H](O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline myo-inositol Identifier CHEBI:17268 (CAS: 87-89-8) help_outline Charge 0 Formula C6H12O6 InChIKeyhelp_outline CDAISMWEOUEBRE-GPIVLXJGSA-N SMILEShelp_outline O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 25 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline indole-3-acetyl-1D-myo-inositol Identifier CHEBI:15711 Charge 0 Formula C16H19NO7 InChIKeyhelp_outline XUACNUJFOIKYPQ-BKQXGZDCSA-N SMILEShelp_outline O[C@H]1[C@H](O)[C@@H](O)[C@H](OC(=O)Cc2c[nH]c3ccccc23)[C@H](O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline D-glucose Identifier CHEBI:4167 (CAS: 2280-44-6) help_outline Charge 0 Formula C6H12O6 InChIKeyhelp_outline WQZGKKKJIJFFOK-GASJEMHNSA-N SMILEShelp_outline OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 163 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:21180 | RHEA:21181 | RHEA:21182 | RHEA:21183 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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UDP-glucose: indoleacetic acid glucosyl transferase and indoleacetyl-glucose: myo-inositol indoleacetyl transferase.
Michalczuk L., Bandurski R.S.
Biochem Biophys Res Commun 93:588-592(1980) [PubMed] [EuropePMC]
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Enzymic synthesis of 1-O-indol-3-ylacetyl-beta-D-glucose and indol-3-ylacetyl-myo-inositol.
Michalczuk L., Bandurski R.S.
An enzyme fraction from extracts of immature kernels of Zea mays catalyses the formation of 1-O-indol-3-ylacetyl-beta-D-glucose from indol-3-ylacetic acid and UDP-glucose. A second enzyme fraction catalyses the formation of indol-3-ylacetyl-myo-inositol from 1-O-indol-3-ylacetyl-beta-D-glucose and ... >> More
An enzyme fraction from extracts of immature kernels of Zea mays catalyses the formation of 1-O-indol-3-ylacetyl-beta-D-glucose from indol-3-ylacetic acid and UDP-glucose. A second enzyme fraction catalyses the formation of indol-3-ylacetyl-myo-inositol from 1-O-indol-3-ylacetyl-beta-D-glucose and myo-inositol. To our knowledge, this is the first example of hydroxy-group acylation by a 1-O-acyl sugar. The following reaction sequence is proposed: Indol-3-ylacetic acid + UDP-glucose leads to indol-3-ylacetylglucose + UDP (1) Indol-3-ylacetylglucose + myo-inositol leads to indol-3-ylacetyl-myo-inositol + glucose (2) The enzyme catalysing reaction (1) is called UDP-glucose:indol-3-ylacetate glucosyl-transferase (indol-3-ylacetylglucose synthase), and that catalysing reaction (2) is indol-3-ylacetylglucose:myo-inositol indol-3-ylacetyltransferase (indol-3-ylacetyl-myo-inositol synthase). We further show that indol-3-ylacetylglucose synthase is specific for UDP-glucose and, at the stage of purity tested, the enzyme will use either indol-3-ylacetic acid or naphthalene-1-acetic acid, but not 2.4-dichlorophenoxyacetic acid, as glucose acceptor. The indol-3-ylacetyl-myo-inositol synthase is specific for indol-3-ylacetyl-glucose and will not use naphthalene-1-acetylglucose as substrate, and it is specific for myo-inositol among the alcohol acceptors tested. Thus, of the auxins tested, only indol-3-ylacetic acid forms the myo-inositol ester. << Less
Biochem J 207:273-281(1982) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.