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Escherichia coli K-12 substr. MG1655 Pathway: UDP-N-acetylmuramoyl-pentapeptide biosynthesis I (meso-DAP-containing)

If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Locations of Mapped Genes:

Genetic Regulation Schematic: ?

Superclasses: Biosynthesis Cell Structures Biosynthesis Cell Wall Biosynthesis UDP-N-Acetylmuramoyl-Pentapeptide Biosynthesis

Summary:
Peptidoglycan is best described as a fisherman's net, with each cell of the mesh defined by two segments of parallel glycan threads, held together by two small elastic peptide crosslinks, which allow the net to expand or shrink [Delcour99]. These peptide crosslinks are usually composed of two pentapeptides, each attached on one end to one of the glycan segment and extending towards (but no reaching) the other one. The two pentapeptides can form a crosslink with each other in more than one way.

The composition and structure of peptidoglycan varies among different bacterial species, but in generals consists of alternating β-1,4-linked N-acetylglucosamine and N-acetylmuramate residues. The pentapeptide is bound through its N terminus to the carboxyl group of muramate.

The pentapeptide, which contains alternating L and D amino acids, reveals considerable variation among species, with the greatest variation found in the third position. This pathway describes the biosynthesis of the UDP-N-acetylmuramoyl-pentapeptide found in most of the Gram-negative organisms and some Gram-positive organisms, which contains meso-diaminopimelate is the third position.

The enzymes of this pathway are essential for growth and thus are attractive targets for antibacterial drug development.

Review: [Barreteau08]

Superpathways: peptidoglycan biosynthesis I (meso-diaminopimelate containing)

Credits:
Created 20-Nov-2009 by Caspi R , SRI International
Last-Curated ? 25-Jul-2013 by Keseler I , SRI International


References

Arthur92: Arthur M, Molinas C, Bugg TD, Wright GD, Walsh CT, Courvalin P (1992). "Evidence for in vivo incorporation of D-lactate into peptidoglycan precursors of vancomycin-resistant enterococci." Antimicrob Agents Chemother 36(4);867-9. PMID: 1503450

Arthur96: Arthur M, Reynolds PE, Depardieu F, Evers S, Dutka-Malen S, Quintiliani R, Courvalin P (1996). "Mechanisms of glycopeptide resistance in enterococci." J Infect 32(1);11-6. PMID: 8852545

Barreteau08: Barreteau H, Kovac A, Boniface A, Sova M, Gobec S, Blanot D (2008). "Cytoplasmic steps of peptidoglycan biosynthesis." FEMS Microbiol Rev 32(2);168-207. PMID: 18266853

Cummins58: Cummins, C.S., Harris, H. (1958). "Studies on the cell-wall composition and taxonomy of Actinomycetales and related groups." J Gen Microbiol 18(1);173-89. PMID: 13525638

Cummins62: Cummins, C.S. (1962). "[The chemical composition of the cell walls of actinomycetes and its taxonomic application.]." Ann Inst Pasteur (Paris) 103;385-91. PMID: 14024243

Cummins62a: Cummins, C.S. (1962). "Chemical composition and antigenic structure of cell walls of Corynebacterium, Mycobacterium, Nocardia, Actinomyces and Arthrobacter." J Gen Microbiol 28;35-50. PMID: 13882624

Cziharz71: Cziharz B, Schleifer KH, Kandler O (1971). "A new type of peptide subunit in the murein of Arthrobacter strain J39." Biochemistry 10(19);3574-8. PMID: 4259817

Delcour99: Delcour J, Ferain T, Deghorain M, Palumbo E, Hols P (1999). "The biosynthesis and functionality of the cell-wall of lactic acid bacteria." Antonie Van Leeuwenhoek 76(1-4);159-84. PMID: 10532377

Fiedler73: Fiedler F, Schleifer K, Kandler O (1973). "Amino acid sequence of the threonine-containing mureins of coryneform bacteria." J Bacteriol 113(1);8-17. PMID: 4683671

Ghuysen68: Ghuysen JM (1968). "Use of bacteriolytic enzymes in determination of wall structure and their role in cell metabolism." Bacteriol Rev 32(4 Pt 2);425-64. PMID: 4884715

Golecki77: Golecki JR (1977). "Studies on ultrastructure and composition of cell walls of the cyanobacterium Anacystis nidulans." Arch Microbiol 114(1);35-41. PMID: 410379

Guinand69: Guinand M, Ghuysen JM, Schleifer KH, Kandler O (1969). "The peptidoglycan in walls of Butyribacterium rettgeri." Biochemistry 8(1);200-7. PMID: 5777324

Interschick70: Interschick, E., Fiedler, F., Schleifer, K.H., Kandler, O. (1970). "Glycine amide a constituent of the murein of Arthrobacter atrocyaneus." Z. Naturforsch 25: 714-717.

Jurgens83: Jurgens UJ, Drews G, Weckesser J (1983). "Primary structure of the peptidoglycan from the unicellular cyanobacterium Synechocystis sp. strain PCC 6714." J Bacteriol 154(1);471-8. PMID: 6131881

Miller66: Miller I, Plapp R, Kandler O (1966). "The amino acid sequence of the serine containing murein of Butybacterium Rettgeri." Biochem Biophys Res Commun 25(4);415-20. PMID: 5965240

Miller68: Miller I, Plapp R, Kandler O (1968). "[Isolation and identification of a serine-containing UDP-muramyltripeptide from Butyribacterium rettgeri]." Z Naturforsch B 23(2);217-20. PMID: 4385976

Mirelman66: Mirelman D, Sharon N (1966). "Isolation and characterization of two disaccharide-peptides from lysozyme digests of Micrococcus lysodeikticus cell walls." Biochem Biophys Res Commun 24(2);237-43. PMID: 5965232

Perkins64: Perkins, H. R., Cummins, C.S. (1964). "Chemical structure of bacterial cell walls. Ornithine and 2,4-diaminobutyric acid as components of the cell walls of plant pathogenic corynebacteria." Nature 201;1105-7. PMID: 14152785

Perkins65: Perkins HR (1965). "2,6-Diamino-3-hydroxypimelic acid in microbial cell wall mucopeptide." Nature 208(13);872-3. PMID: 5870104

Perkins67: Perkins HR (1967). "The use of photolysis of dinitrophenyl-peptides in structural studies on the cell-wall mucopeptide of Corynebacterium poinsettiae." Biochem J 102(2);29C-32C. PMID: 6029599

Perkins68: Perkins HR (1968). "Cell-wall mucopeptide of Corynebacterium insidiosum and Corynebacterium sepedonicum." Biochem J 110(4);47P-48P. PMID: 5704800

Perkins71: Perkins HR (1971). "Homoserine and diaminobutyric acid in the mucopeptide-precursor-nucleotides and cell walls of some plant-pathogenic corynebacteria." Biochem J 121(3);417-23. PMID: 5119774

Plapp67: Plapp R, Kandler O (1967). "Isolation of an ornithine-containing cell wall precursor of Lactobacillus cellobiosus." Biochem Biophys Res Commun 28(2);141-5. PMID: 6035494

Plapp67a: Plapp R, Kandler O (1967). "Identification of L-ornithine and delta-aminosuccinyl ornithine in cell wall hydrolysates of Lactobacillus cellobiosus." Nature 213(78);803-4. PMID: 6031807

Schleifer67: Schleifer KH, Plapp R, Kandler O (1967). "The amino acid sequence of a glycine-containing cell wall precursor of Microbacterium lacticum." Biochem Biophys Res Commun 26(4);492-6. PMID: 6033749

Schleifer67a: Schleifer KH, Plapp R, Kandler O (1967). "Identification of threo-3-hydroxyglutamic acid in the cell wall of Microbacterium lacticum." Biochem Biophys Res Commun 28(4);566-70. PMID: 6072398

Schleifer67b: Schleifer KH, Kandler O (1967). "Micrococcus lysodeikticus: a new type of cross-linkage of the murein." Biochem Biophys Res Commun 28(6);965-72. PMID: 6064598

Schleifer68: Schleifer KH, Plapp R, Kandler O (1968). "Glycine as crosslinking bridge in the LL-diaminopimelic acid containing murein of Propionibacterium peterssonii." FEBS Lett 1(5);287-290. PMID: 11945321

Schleifer70: Schleifer KH (1970). "[The murein types of the genus Microbacterium]." Arch Mikrobiol 71(3);271-82. PMID: 5469569

Shockman65: Shockman GD, Thompson JS, Conover MJ (1965). "Replacement of Lysine by Hydroxylysine and Its Effects on Cell Lysis in Streptococcus faecalis." J Bacteriol 90(3);575-88. PMID: 16562051

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

AboGhalia85: Abo-Ghalia M, Michaud C, Blanot D, van Heijenoort J (1985). "Specificity of the uridine-diphosphate-N-acetylmuramyl-L-alanyl-D-glutamate: meso-2,6-diaminopimelate synthetase from Escherichia coli." Eur J Biochem 1985;153(1);81-7. PMID: 3905407

AboGhalia88: Abo-Ghalia M, Flegel M, Blanot D, Van Heijenoort J (1988). "Synthesis of inhibitors of the meso-diaminopimelate-adding enzyme from Escherichia coli." Int J Pept Protein Res 32(3);208-22. PMID: 3072305

alBar92: al-Bar OA, O'Connor CD, Giles IG, Akhtar M (1992). "D-alanine: D-alanine ligase of Escherichia coli. Expression, purification and inhibitory studies on the cloned enzyme." Biochem J 282 ( Pt 3);747-52. PMID: 1554356

Anderson96: Anderson MS, Eveland SS, Onishi HR, Pompliano DL (1996). "Kinetic mechanism of the Escherichia coli UDPMurNAc-tripeptide D-alanyl-D-alanine-adding enzyme: use of a glutathione S-transferase fusion." Biochemistry 35(50);16264-9. PMID: 8973200

Anwar79: Anwar RA, Vlaovic M (1979). "Purification of UDP-N-acetylenolpyruvoylglucosamine reductase from Escherichia coli by affinity chromatography, its subunit structure and the absence of flavin as the prosthetic group." Can J Biochem 1979;57(2);188-96. PMID: 36973

Ashiuchi02: Ashiuchi M, Kuwana E, Yamamoto T, Komatsu K, Soda K, Misono H (2002). "Glutamate racemase is an endogenous DNA gyrase inhibitor." J Biol Chem 277(42);39070-3. PMID: 12213801

Ashiuchi95: Ashiuchi M, Yoshimura T, Kitamura T, Kawata Y, Nagai J, Gorlatov S, Esaki N, Soda K (1995). "In vivo effect of GroESL on the folding of glutamate racemase of Escherichia coli." J Biochem 117(3);495-8. PMID: 7629013

Auger96: Auger G, van Heijenoort J, Vederas JC, Blanot D (1996). "Effect of analogues of diaminopimelic acid on the meso-diaminopimelate-adding enzyme from Escherichia coli." FEBS Lett 391(1-2);171-4. PMID: 8706910

Auger98: Auger G, Martin L, Bertrand J, Ferrari P, Fanchon E, Vaganay S, Petillot Y, van Heijenoort J, Blanot D, Dideberg O (1998). "Large-scale preparation, purification, and crystallization of UDP-N-acetylmuramoyl-L-alanine: D-glutamate ligase from Escherichia coli." Protein Expr Purif 13(1);23-9. PMID: 9631510

Axley97: Axley MJ, Fairman R, Yanchunas J, Villafranca JJ, Robertson JG (1997). "Spectroscopic properties of Escherichia coli UDP-N-acetylenolpyruvylglucosamine reductase." Biochemistry 36(4);812-22. PMID: 9020779

Baba06: Baba T, Ara T, Hasegawa M, Takai Y, Okumura Y, Baba M, Datsenko KA, Tomita M, Wanner BL, Mori H (2006). "Construction of Escherichia coli K-12 in-frame, single-gene knockout mutants: the Keio collection." Mol Syst Biol 2;2006.0008. PMID: 16738554

Bachelier06: Bachelier A, Mayer R, Klein CD (2006). "Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA." Bioorg Med Chem Lett 16(21);5605-9. PMID: 16945528

Baliko88: Baliko G, Raukas A, Boros I, Venetianer P (1988). "An Escherichia coli gene in search of a function." Mol Gen Genet 211(2);326-31. PMID: 2832706

Baliko93: Baliko G, Venetianer P (1993). "An Escherichia coli gene in search of a function: phenotypic effects of the gene recently identified as murI." J Bacteriol 175(20);6571-7. PMID: 8407834

Barbosa02a: Barbosa MD, Yang G, Fang J, Kurilla MG, Pompliano DL (2002). "Development of a whole-cell assay for peptidoglycan biosynthesis inhibitors." Antimicrob Agents Chemother 46(4);943-6. PMID: 11897573

Barreteau12: Barreteau H, Sosič I, Turk S, Humljan J, Tomašić T, Zidar N, Herve M, Boniface A, Peterlin-Mašič L, Kikelj D, Mengin-Lecreulx D, Gobec S, Blanot D (2012). "MurD enzymes from different bacteria: evaluation of inhibitors." Biochem Pharmacol 84(5);625-32. PMID: 22705647

Batson10: Batson S, Rea D, Fulop V, Roper DI (2010). "Crystallization and preliminary X-ray analysis of a D-alanyl-D-alanine ligase (EcDdlB) from Escherichia coli." Acta Crystallogr Sect F Struct Biol Cryst Commun 66(Pt 4);405-8. PMID: 20383009

Baum01: Baum EZ, Montenegro DA, Licata L, Turchi I, Webb GC, Foleno BD, Bush K (2001). "Identification and characterization of new inhibitors of the Escherichia coli MurA enzyme." Antimicrob Agents Chemother 45(11);3182-8. PMID: 11600375

Baum06: Baum EZ, Crespo-Carbone SM, Abbanat D, Foleno B, Maden A, Goldschmidt R, Bush K (2006). "Utility of muropeptide ligase for identification of inhibitors of the cell wall biosynthesis enzyme MurF." Antimicrob Agents Chemother 50(1);230-6. PMID: 16377691

Baum07: Baum EZ, Crespo-Carbone SM, Klinger A, Foleno BD, Turchi I, Macielag M, Bush K (2007). "A MurF inhibitor that disrupts cell wall biosynthesis in Escherichia coli." Antimicrob Agents Chemother 51(12);4420-6. PMID: 17908943

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 28, 2014, biocyc12.