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- Name help_outline (2R)-2-O-[α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl]-glycerate Identifier CHEBI:141056 Charge -1 Formula C15H25O14 InChIKeyhelp_outline DMTGFWVSBPXWQU-WSLUIUCSSA-M SMILEShelp_outline [C@@H]1(O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)O[C@H](CO)C([O-])=O)CO[C@@H]2[C@H](O)[C@@H](O)[C@@H]([C@H](O2)CO)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 octanoyl-CoA Identifier CHEBI:57386 Charge -4 Formula C29H46N7O17P3S InChIKeyhelp_outline KQMZYOXOBSXMII-CECATXLMSA-J SMILEShelp_outline CCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12 2D coordinates Mol file for the small molecule Search links Involved in 31 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (2R)-2-O-[6-O-octanoyl-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl]-glycerate Identifier CHEBI:141058 Charge -1 Formula C23H39O15 InChIKeyhelp_outline VGKUTDQBPZMQAK-LOPSRDRFSA-M SMILEShelp_outline [C@@H]1(O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)O[C@H](CO)C([O-])=O)CO[C@@H]2[C@H](O)[C@@H](O)[C@@H]([C@H](O2)COC(CCCCCCC)=O)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 CoA Identifier CHEBI:57287 (Beilstein: 11604429) help_outline Charge -4 Formula C21H32N7O16P3S InChIKeyhelp_outline RGJOEKWQDUBAIZ-IBOSZNHHSA-J SMILEShelp_outline CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCS 2D coordinates Mol file for the small molecule Search links Involved in 1,468 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:56868 | RHEA:56869 | RHEA:56870 | RHEA:56871 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Octanoylation of early intermediates of mycobacterial methylglucose lipopolysaccharides.
Maranha A., Moynihan P.J., Miranda V., Correia Lourenco E., Nunes-Costa D., Fraga J.S., Jose Barbosa Pereira P., Macedo-Ribeiro S., Ventura M.R., Clarke A.J., Empadinhas N.
Mycobacteria synthesize unique intracellular methylglucose lipopolysaccharides (MGLP) proposed to modulate fatty acid metabolism. In addition to the partial esterification of glucose or methylglucose units with short-chain fatty acids, octanoate was invariably detected on the MGLP reducing end. We ... >> More
Mycobacteria synthesize unique intracellular methylglucose lipopolysaccharides (MGLP) proposed to modulate fatty acid metabolism. In addition to the partial esterification of glucose or methylglucose units with short-chain fatty acids, octanoate was invariably detected on the MGLP reducing end. We have identified a novel sugar octanoyltransferase (OctT) that efficiently transfers octanoate to glucosylglycerate (GG) and diglucosylglycerate (DGG), the earliest intermediates in MGLP biosynthesis. Enzymatic studies, synthetic chemistry, NMR spectroscopy and mass spectrometry approaches suggest that, in contrast to the prevailing consensus, octanoate is not esterified to the primary hydroxyl group of glycerate but instead to the C6 OH of the second glucose in DGG. These observations raise important new questions about the MGLP reducing end architecture and about subsequent biosynthetic steps. Functional characterization of this unique octanoyltransferase, whose gene has been proposed to be essential for M. tuberculosis growth, adds new insights into a vital mycobacterial pathway, which may inspire new drug discovery strategies. << Less
Sci. Rep. 5:13610-13610(2015) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.