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- Name help_outline bis(myo-inositol) 1,3'-phosphate Identifier CHEBI:142886 Charge -1 Formula C12H22O14P InChIKeyhelp_outline FIIUDBCIQWHEHT-VOEMVRBLSA-M SMILEShelp_outline [C@H]1([C@@H]([C@@H]([C@H]([C@@H]([C@H]1O)O)O)O)O)OP(=O)(O[C@H]2[C@H]([C@H]([C@@H]([C@H]([C@@H]2O)O)O)O)O)[O-] 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 GDP-α-D-mannose Identifier CHEBI:57527 (Beilstein: 6630718) help_outline Charge -2 Formula C16H23N5O16P2 InChIKeyhelp_outline MVMSCBBUIHUTGJ-GDJBGNAASA-L SMILEShelp_outline Nc1nc2n(cnc2c(=O)[nH]1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 52 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 2-O-(β-D-mannosyl-(1→2)-β-D-mannosyl)-bis(myo-inositol) 1,3'-phosphate Identifier CHEBI:142887 Charge -1 Formula C24H42O24P InChIKeyhelp_outline PMUCECFZOHGHSS-PHIWOPILSA-M SMILEShelp_outline [C@H]1([C@@H]([C@@H]([C@H]([C@@H]([C@H]1O)O)O)O)O)OP(=O)(O[C@H]2[C@H]([C@H]([C@@H]([C@H]([C@@H]2O)O)O)O)O[C@@H]3[C@H]([C@H]([C@H](O)[C@H](O3)CO)O)O[C@@H]4[C@H]([C@H]([C@H](O)[C@H](O4)CO)O)O)[O-] 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 GDP Identifier CHEBI:58189 Charge -3 Formula C10H12N5O11P2 InChIKeyhelp_outline QGWNDRXFNXRZMB-UUOKFMHZSA-K SMILEShelp_outline Nc1nc2n(cnc2c(=O)[nH]1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 169 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
Cross-references
| RHEA:59076 | RHEA:59077 | RHEA:59078 | RHEA:59079 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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| EC numbers help_outline |
Publications
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A unique beta-1,2-mannosyltransferase of Thermotoga maritima that uses di-myo-inositol phosphate as the mannosyl acceptor.
Rodrigues M.V., Borges N., Almeida C.P., Lamosa P., Santos H.
In addition to di-myo-inositol-1,3'-phosphate (DIP), a compatible solute widespread in hyperthermophiles, the organic solute pool of Thermotoga maritima comprises 2-(O-beta-D-mannosyl)-di-myo-inositol-1,3'-phosphate (MDIP) and 2-(O-beta-D-mannosyl-1,2-O-beta-D-mannosyl)-di-myo-inositol-1,3'-phosph ... >> More
In addition to di-myo-inositol-1,3'-phosphate (DIP), a compatible solute widespread in hyperthermophiles, the organic solute pool of Thermotoga maritima comprises 2-(O-beta-D-mannosyl)-di-myo-inositol-1,3'-phosphate (MDIP) and 2-(O-beta-D-mannosyl-1,2-O-beta-D-mannosyl)-di-myo-inositol-1,3'-phosphate (MMDIP), two newly identified beta-1,2-mannosides. In cells grown under heat stress, MDIP was the major solute, accounting for 43% of the total pool; MMDIP and DIP accumulated to similar levels, each corresponding to 11.5% of the total pool. The synthesis of MDIP involved the transfer of the mannosyl group from GDP-mannose to DIP in a single-step reaction catalyzed by MDIP synthase. This enzyme used MDIP as an acceptor of a second mannose residue, yielding the di-mannosylated compound. Minor amounts of the tri-mannosylated form were also detected. With a genomic approach, putative genes for MDIP synthase were identified in the genome of T. maritima, and the assignment was confirmed by functional expression in Escherichia coli. Genes with significant sequence identity were found only in the genomes of Thermotoga spp., Aquifex aeolicus, and Archaeoglobus profundus. MDIP synthase of T. maritima had maximal activity at 95 degrees C and apparent K(m) values of 16 mM and 0.7 mM for DIP and GDP-mannose, respectively. The stereochemistry of MDIP was characterized by isotopic labeling and nuclear magnetic resonance (NMR): DIP selectively labeled with carbon 13 at position C1 of the l-inositol moiety was synthesized and used as a substrate for MDIP synthase. This beta-1,2-mannosyltransferase is unrelated to known glycosyltransferases, and within the domain Bacteria, it is restricted to members of the two deepest lineages, i.e., the Thermotogales and the Aquificales. To our knowledge, this is the first beta-1,2-mannosyltransferase characterized thus far. << Less
J. Bacteriol. 191:6105-6115(2009) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.
Comments
Multi-step reaction: RHEA:59080 + RHEA:59084