Reaction participants Show >> << Hide
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Name help_outline
4-O-[poly(D-ribitylphospho)-D-ribitylphospho-(2R)-glycerylphospho]-N-acetyl-β-D-mannosaminyl-(1→4)-N-acetyl-α-D-glucosaminyl di-trans,octa-cis-undecaprenyl diphosphate
Identifier
CHEBI:133894
Charge
-5
Formula
(C5H10O7P)n.C79H132N2O29P4
Search links
Involved in 2 reaction(s)
Find proteins in UniProtKB for this molecule
Form(s) in this reaction:
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Identifier: RHEA-COMP:12833Polymer name: 4-O-[(D-ribitylphospho)(n)-D-ribitylphospho-(2R)-glycerylphospho]-N-acetyl-β-D-mannosaminyl-(1→4)-N-acetyl-α-D-glucosaminyl di-trans,octa-cis-undecaprenyl diphosphatePolymerization index help_outline nFormula C79H132N2O29P4(C5H10O7P)nCharge (-4)(-1)nMol File for the polymer
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- Name help_outline UDP-α-D-glucose Identifier CHEBI:58885 (Beilstein: 3827329) help_outline Charge -2 Formula C15H22N2O17P2 InChIKeyhelp_outline HSCJRCZFDFQWRP-JZMIEXBBSA-L SMILEShelp_outline OC[C@H]1O[C@H](OP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)n2ccc(=O)[nH]c2=O)[C@H](O)[C@@H](O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 225 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Name help_outline
4-O-[(2-β-D-glucosyl-1-D-ribitylphospho)n-1-D-ribitylphospho-(2R)-1-glycerylphospho]-N-acetyl-β-D-mannosaminyl-(1→4)-N-acetyl-α-D-glucosaminyl ditrans,octacis-undecaprenyl diphosphate polyanion
Identifier
CHEBI:139149
Charge
-5
Formula
(C11H20O12P)n.C79H132N2O29P4
Search links
Involved in 1 reaction(s)
Find proteins in UniProtKB for this molecule
Form(s) in this reaction:
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Identifier: RHEA-COMP:14260Polymer name: 4-O-[(2-β-D-glucosyl-D-ribitylphospho)(n)-D-ribitylphospho-(2R)-glycerylphospho]-N-acetyl-β-D-mannosaminyl-(1→4)-N-acetyl-α-D-glucosaminyl di-trans,octa-cis-undecaprenyl diphosphatePolymerization index help_outline nFormula C79H132N2O29P4(C11H20O12P)nCharge (-4)(-1)nMol File for the polymer
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- 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 9,331 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 562 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
RHEA:10068 | RHEA:10069 | RHEA:10070 | RHEA:10071 | |
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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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Methicillin resistance in Staphylococcus aureus requires glycosylated wall teichoic acids.
Brown S., Xia G., Luhachack L.G., Campbell J., Meredith T.C., Chen C., Winstel V., Gekeler C., Irazoqui J.E., Peschel A., Walker S.
Staphylococcus aureus peptidoglycan (PG) is densely functionalized with anionic polymers called wall teichoic acids (WTAs). These polymers contain three tailoring modifications: d-alanylation, α-O-GlcNAcylation, and β-O-GlcNAcylation. Here we describe the discovery and biochemical characterization ... >> More
Staphylococcus aureus peptidoglycan (PG) is densely functionalized with anionic polymers called wall teichoic acids (WTAs). These polymers contain three tailoring modifications: d-alanylation, α-O-GlcNAcylation, and β-O-GlcNAcylation. Here we describe the discovery and biochemical characterization of a unique glycosyltransferase, TarS, that attaches β-O-GlcNAc (β-O-N-acetyl-D-glucosamine) residues to S. aureus WTAs. We report that methicillin resistant S. aureus (MRSA) is sensitized to β-lactams upon tarS deletion. Unlike strains completely lacking WTAs, which are also sensitive to β-lactams, ΔtarS strains have no growth or cell division defects. Because neither α-O-GlcNAc nor β-O-Glucose modifications can confer resistance, the resistance phenotype requires a highly specific chemical modification of the WTA backbone, β-O-GlcNAc residues. These data suggest β-O-GlcNAcylated WTAs scaffold factors required for MRSA resistance. The β-O-GlcNAc transferase identified here, TarS, is a unique target for antimicrobials that sensitize MRSA to β-lactams. << Less
Proc. Natl. Acad. Sci. U.S.A. 109:18909-18914(2012) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.