Reaction participants Show >> << Hide
- Name help_outline a 1D-myo-inositol-1-phospho-N-[(R)-2-hydroxy-very-long-chain fatty acyl]-(R)-4-hydroxysphingoid base Identifier CHEBI:155926 Charge -1 Formula C12H21NO13PR2 SMILEShelp_outline [C@@H]([C@H](COP(=O)(O[C@H]1[C@@H]([C@H]([C@@H]([C@H]([C@H]1O)O)O)O)O)[O-])NC([C@@H](*)O)=O)(O)[C@@H](*)O 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 UDP-α-D-glucuronate Identifier CHEBI:58052 Charge -3 Formula C15H19N2O18P2 InChIKeyhelp_outline HDYANYHVCAPMJV-LXQIFKJMSA-K SMILEShelp_outline O[C@@H]1[C@@H](COP([O-])(=O)OP([O-])(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C([O-])=O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O 2D coordinates Mol file for the small molecule Search links Involved in 94 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline an α-D-glucuronosyl-(1↔6)-1D-myo-inositol-1-phospho-N-[(R)-2-hydroxy-very-long-chain fatty acyl]-(R)-4-hydroxysphingoid base Identifier CHEBI:156567 Charge -2 Formula C18H28NO19PR2 SMILEShelp_outline [C@@H]([C@H](COP([O-])(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H]([C@H]1O)O)O)O)O[C@H]2O[C@@H]([C@H]([C@@H]([C@H]2O)O)O)C(=O)[O-])NC([C@@H](*)O)=O)(O)[C@@H](*)O 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline UDP Identifier CHEBI:58223 Charge -3 Formula C9H11N2O12P2 InChIKeyhelp_outline XCCTYIAWTASOJW-XVFCMESISA-K SMILEShelp_outline O[C@@H]1[C@@H](COP([O-])(=O)OP([O-])([O-])=O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O 2D coordinates Mol file for the small molecule Search links Involved in 542 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:65576 | RHEA:65577 | RHEA:65578 | RHEA:65579 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
|
Publications
-
Identification of a sphingolipid alpha-glucuronosyltransferase that is essential for pollen function in Arabidopsis.
Rennie E.A., Ebert B., Miles G.P., Cahoon R.E., Christiansen K.M., Stonebloom S., Khatab H., Twell D., Petzold C.J., Adams P.D., Dupree P., Heazlewood J.L., Cahoon E.B., Scheller H.V.
Glycosyl inositol phosphorylceramide (GIPC) sphingolipids are a major class of lipids in fungi, protozoans, and plants. GIPCs are abundant in the plasma membrane in plants, comprising around a quarter of the total lipids in these membranes. Plant GIPCs contain unique glycan decorations that includ ... >> More
Glycosyl inositol phosphorylceramide (GIPC) sphingolipids are a major class of lipids in fungi, protozoans, and plants. GIPCs are abundant in the plasma membrane in plants, comprising around a quarter of the total lipids in these membranes. Plant GIPCs contain unique glycan decorations that include a conserved glucuronic acid (GlcA) residue and various additional sugars; however, no proteins responsible for glycosylating GIPCs have been identified to date. Here, we show that the Arabidopsis thaliana protein INOSITOL PHOSPHORYLCERAMIDE GLUCURONOSYLTRANSFERASE1 (IPUT1) transfers GlcA from UDP-GlcA to GIPCs. To demonstrate IPUT1 activity, we introduced the IPUT1 gene together with genes for a UDP-glucose dehydrogenase from Arabidopsis and a human UDP-GlcA transporter into a yeast mutant deficient in the endogenous inositol phosphorylceramide (IPC) mannosyltransferase. In this engineered yeast strain, IPUT1 transferred GlcA to IPC. Overexpression or silencing of IPUT1 in Nicotiana benthamiana resulted in an increase or a decrease, respectively, in IPC glucuronosyltransferase activity in vitro. Plants in which IPUT1 was silenced accumulated IPC, the immediate precursor, as well as ceramides and glucosylceramides. Plants overexpressing IPUT1 showed an increased content of GIPCs. Mutations in IPUT1 are not transmitted through pollen, indicating that these sphingolipids are essential in plants. << Less
Plant Cell 26:3314-3325(2014) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.
Comments
The 2-hydroxy group on the very long-chain fatty acid (VLFA) is believed to be in (R) configuration but the compound has actually not been purified and characterized.