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Name ^help_outline 4-O-({poly[(2R)-glycerylphospho]}-(2R)-glycerylphospho)-N-acetyl-β-D-mannosaminyl-(1→4)-N-acetyl-α-D-glucosaminyl undecaprenyl diphosphate Identifier CHEBI:132224 Charge Formula (C3H6O5P)n.C74H122N2O22P3 Search links Involved in 2 reaction(s) Find proteins in UniProtKB for this molecule Form(s) in this reaction:
- Identifier: RHEA-COMP:12597
  
  Polymer name: 4-O-{[(2R)-1-glycerylphospho]_(n)-(2R)-1-glycerylphospho}-N-acetyl-β-D-mannosaminyl-(1→4)-N-acetyl-α-D-glucosaminyl undecaprenyl diphosphate
  
  Polymerization index ^help_outline n
  
  Formula C74H122N2O22P3(C3H6O5P)_n
  
  Charge (-3)(-1)_n
  Mol File for the polymer
Name ^help_outline UDP-α-D-glucose Identifier CHEBI:58885 (Beilstein: 3827329) ^help_outline Charge -2 Formula C15H22N2O17P2 InChIKey^help_outline HSCJRCZFDFQWRP-JZMIEXBBSA-L SMILES^help_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 231 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline 4-O-({poly[(2R)-2-α-D-glycosyl-glycerylphospho]}-(2R)-glycerylphospho)-N-acetyl-β-D-mannosaminyl-(1→4)-N-acetyl-α-D-glucosaminyl undecaprenyl diphosphate Identifier CHEBI:132356 Charge Formula (C9H16O10P)n.C74H122N2O22P3 Search links Involved in 1 reaction(s) Find proteins in UniProtKB for this molecule Form(s) in this reaction:
- Identifier: RHEA-COMP:12614
  
  Polymer name: 4-O-{[(2R)-2-α-D-glucosyl-1-glycerylphospho]_(n)-(2R)-1-glycerylphospho}-N-acetyl-β-D-mannosaminyl-(1→4)-N-acetyl-α-D-glucosaminyl undecaprenyl diphosphate
  
  Polymerization index ^help_outline n
  
  Formula C74H122N2O22P3(C9H16O10P)_n
  
  Charge (-3)(-1)_n
  Mol File for the polymer
Name ^help_outline UDP Identifier CHEBI:58223 Charge -3 Formula C9H11N2O12P2 InChIKey^help_outline XCCTYIAWTASOJW-XVFCMESISA-K SMILES^help_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 577 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 InChIKey^help_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILES^help_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,521 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:15845	RHEA:15846	RHEA:15847	RHEA:15848
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	1 proteins
EC numbers ^help_outline	2.4.1.52
Gene Ontology ^help_outline	GO:0047265
KEGG ^help_outline				R04041
MetaCyc ^help_outline		TEICHOICSYN5-RXN

Publications

THE SYNTHESIS OF TEICHOIC ACIDS. 3. GLUCOSYLATION OF POLYGLYCEROPHOSPHATE.

GLASER L., BURGER M.M.

J Biol Chem 239:3187-3191(1964) [PubMed] [EuropePMC]
Studies of the genetics, function, and kinetic mechanism of TagE, the wall teichoic acid glycosyltransferase in Bacillus subtilis 168.

Allison S.E., D'Elia M.A., Arar S., Monteiro M.A., Brown E.D.

The biosynthetic enzymes involved in wall teichoic acid biogenesis in gram-positive bacteria have been the subject of renewed investigation in recent years with the benefit of modern tools of biochemistry and genetics. Nevertheless, there have been only limited investigations into the enzymes that ... >> More

The biosynthetic enzymes involved in wall teichoic acid biogenesis in gram-positive bacteria have been the subject of renewed investigation in recent years with the benefit of modern tools of biochemistry and genetics. Nevertheless, there have been only limited investigations into the enzymes that glycosylate wall teichoic acid. Decades-old experiments in the model gram-positive bacterium, Bacillus subtilis 168, using phage-resistant mutants implicated tagE (also called gtaA and rodD) as the gene coding for the wall teichoic acid glycosyltransferase. This study and others have provided only indirect evidence to support a role for TagE in wall teichoic acid glycosylation. In this work, we showed that deletion of tagE resulted in the loss of α-glucose at the C-2 position of glycerol in the poly(glycerol phosphate) polymer backbone. We also reported the first kinetic characterization of pure, recombinant wall teichoic acid glycosyltransferase using clean synthetic substrates. We investigated the substrate specificity of TagE using a wide variety of acceptor substrates and found that the enzyme had a strong kinetic preference for the transfer of glucose from UDP-glucose to glycerol phosphate in polymeric form. Further, we showed that the enzyme recognized its polymeric (and repetitive) substrate with a sequential kinetic mechanism. This work provides direct evidence that TagE is the wall teichoic acid glycosyltransferase in B. subtilis 168 and provides a strong basis for further studies of the mechanism of wall teichoic acid glycosylation, a largely uncharted aspect of wall teichoic acid biogenesis. << Less

J. Biol. Chem. 286:23708-23716(2011) [PubMed] [EuropePMC]
Genes concerned with synthesis of poly(glycerol phosphate), the essential teichoic acid in Bacillus subtilis strain 168, are organized in two divergent transcription units.

Maueel C., Young M., Karamata D.

Insertional mutagenesis has revealed that a 22 kbp segment from the hisA region of the Bacillus subtilis 168 chromosome (310 degrees on the genetic map) contains at least six independent transcription units, all apparently devoted to production of cell envelope components. Genes concerned with syn ... >> More

Insertional mutagenesis has revealed that a 22 kbp segment from the hisA region of the Bacillus subtilis 168 chromosome (310 degrees on the genetic map) contains at least six independent transcription units, all apparently devoted to production of cell envelope components. Genes concerned with synthesis of poly(glycerol phosphate), poly(groP), an essential cell wall polymer in B. subtilis 168, are organized in two divergently transcribed operons denoted tagABC and tagDEF. Nucleotide sequence analysis indicates that three of these six genes encode extremely basic polypeptides. The deduced products of the tagABC operon may be involved in poly(groP) assembly and export, whereas those of the tagDEF operon, which are very hydrophilic, are more likely to be implicated in poly(groP) precursor biosynthesis. The first gene of the tagDEF operon encodes glycerol-3-phosphate cytidylyltransferase (Pooley et al., 1991, Journal of General Microbiology 137, 921-928) and its deduced product has significant homology with cholinephosphate cytidylyltransferase from yeast. There is also substantial homology between the deduced products of tagB in the tagABC operon and tagF in the tagDEF operon. << Less

J. Gen. Microbiol. 137:929-941(1991) [PubMed] [EuropePMC]

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Cross-references

Publications

THE SYNTHESIS OF TEICHOIC ACIDS. 3. GLUCOSYLATION OF POLYGLYCEROPHOSPHATE.

Studies of the genetics, function, and kinetic mechanism of TagE, the wall teichoic acid glycosyltransferase in Bacillus subtilis 168.

Genes concerned with synthesis of poly(glycerol phosphate), the essential teichoic acid in Bacillus subtilis strain 168, are organized in two divergent transcription units.