KEGG   PATHWAY: eoh00540
Entry
eoh00540                    Pathway                                
Name
Lipopolysaccharide biosynthesis - Escherichia coli O103:H2 12009 (EHEC)
Description
Lipopolysaccharide (LPS) is the major component of the outer membrane of Gram-negative bacteria consisting of three domains: a hydrophobic anchor called lipid A, a non-repeating core oligosaccharide (OS) and a repetitive glycan polymer called O-antigen or O-polysaccharide (O-PS). The enzymes for the biosynthesis of lipid A are well conserved among Gram-negative bacterial species [MD:M00060 M00866]. The core OS connecting lipid A with O-antigen is divided into inner and outer parts. Five core types, K-12 and R1-R4, are identified in Escherichia coli, with the common inner part composed of Kdo (ketodeoxyoctulosonic acid) and Hep (heptose) residues and the outer part made of various sugar residues. O-antigen is the most variable part used for serotyping of pathogenic Escherichia coli, where about 170 types are known. All three domains are involved in toxicity, pathogenicity, antimicrobial resistance and other activities.
Class
Metabolism; Glycan biosynthesis and metabolism
Pathway map
eoh00540  Lipopolysaccharide biosynthesis
eoh00540

Module
eoh_M00060  KDO2-lipid A biosynthesis, Raetz pathway, LpxL-LpxM type [PATH:eoh00540]
eoh_M00063  CMP-KDO biosynthesis [PATH:eoh00540]
eoh_M00064  ADP-L-glycero-D-manno-heptose biosynthesis [PATH:eoh00540]
Other DBs
GO: 0009103
Organism
Escherichia coli O103:H2 12009 (EHEC) [GN:eoh]
Gene
ECO103_0179  lpxA; UDP-N-acetylglucosamine acetyltransferase [KO:K00677] [EC:2.3.1.129]
ECO103_0098  lpxC; UDP-3-O-acyl N-acetylglucosamine deacetylase [KO:K02535] [EC:3.5.1.108]
ECO103_0177  lpxD; UDP-3-O-(3-hydroxymyristoyl)-glucosamine N-acyltransferase [KO:K02536] [EC:2.3.1.191]
ECO103_0496  lpxH; UDP-2,3-diacylglucosamine pyrophosphatase [KO:K03269] [EC:3.6.1.54]
ECO103_0180  lpxB; tetraacyldisaccharide-1-P synthase [KO:K00748] [EC:2.4.1.182]
ECO103_0958  lpxK; lipid A 4'-kinase [KO:K00912] [EC:2.7.1.130]
ECO103_3944  kdsD; D-arabinose 5-phosphate isomerase [KO:K06041] [EC:5.3.1.13]
ECO103_1317  kdsA; 3-deoxy-D-manno-octulosonate 8-phosphate synthase [KO:K01627] [EC:2.5.1.55]
ECO103_3945  kdsC; 3-deoxy-D-manno-octulosonate 8-phosphate phosphatase [KO:K03270] [EC:3.1.3.45]
ECO103_0962  kdsB; 3-deoxy-manno-octulosonate cytidylyltransferase [KO:K00979] [EC:2.7.7.38]
ECO103_4549  kdtA; 3-deoxy-D-manno-octulosonic-acid transferase [KO:K02527] [EC:2.4.99.12 2.4.99.13 2.4.99.14 2.4.99.15]
ECO103_1099  lpxL; lauryl-acyl carrier protein (ACP)-dependent acyltransferase [KO:K02517] [EC:2.3.1.241 2.3.1.-]
ECO103_2045  lpxM; myristoyl-acyl carrier protein (ACP)-dependent acyltransferase [KO:K02560] [EC:2.3.1.243]
ECO103_p23  putative lipid A myristoyl transferase MsbB2 [KO:K02560] [EC:2.3.1.243]
ECO103_0766  putative systemic factor protein SfpA [KO:K09953] [EC:3.1.1.-]
ECO103_2651  yeiU; undecaprenyl pyrophosphate phosphatase [KO:K19803] [EC:2.7.4.29]
ECO103_3792  putative membrane-associated, metal-dependent hydrolase [KO:K03760] [EC:2.7.8.43]
ECO103_4866  eptA; predicted metal dependent hydrolase EptA [KO:K03760] [EC:2.7.8.43]
ECO103_4693  eptB; predicted metal dependent hydrolase EptB [KO:K12975] [EC:2.7.8.42]
ECO103_0630  crcA; palmitoyl transferase CrcA for Lipid A [KO:K12973] [EC:2.3.1.251]
ECO103_2723  arnT; 4-amino-4-deoxy-L-arabinose transferase ArnT [KO:K07264] [EC:2.4.2.43]
ECO103_2903  ddg; palmitoleoyl-acyl carrier protein (ACP)-dependentacyltransferase Ddg [KO:K12974] [EC:2.3.1.242]
ECO103_0238  lpcA; D-sedoheptulose 7-phosphate isomerase [KO:K03271] [EC:5.3.1.28]
ECO103_3732  rfaE; fused heptose 7-phosphate kinase/heptose 1-phosphate adenyltransferase [KO:K03272] [EC:2.7.1.167 2.7.7.70]
ECO103_0200  gmhB; D,D-heptose 1,7-bisphosphate phosphatase [KO:K03273] [EC:3.1.3.82 3.1.3.83]
ECO103_4560  rfaD; ADP-L-glycero-D-mannoheptose-6-epimerase, NAD(P)-binding RfaD [KO:K03274] [EC:5.1.3.20]
ECO103_4558  rfaC; ADP-heptose: LPS heptosyl transferase I RfaC [KO:K02841] [EC:2.4.99.23]
ECO103_4559  rfaF; ADP-heptose: LPS heptosyl transferase II RfaF [KO:K02843] [EC:2.4.99.24]
ECO103_4552  rfaP; lipopolysaccharide core biosynthesis protein FfaP [KO:K02848] [EC:2.7.1.235]
ECO103_4711  yijP; conserved predicted inner membrane protein [KO:K19353] [EC:2.7.8.-]
ECO103_4550  rfaQ; lipopolysaccharide core biosynthesis protein RfaQ [KO:K02849] [EC:2.4.99.25]
ECO103_p21  putative LPS -1,7-N-acetylglucosamine transferase [KO:K23160]
ECO103_4564  yibD; predicted glycosyl transferase [KO:K19354] [EC:2.4.1.-]
ECO103_4554  waaY; lipopolysaccharide core biosynthesis protein WaaY [KO:K02850] [EC:2.7.1.-]
ECO103_4551  rfaG; glucosyltransferase I RfaG [KO:K02844] [EC:2.4.1.-]
ECO103_4553  UDP-D-galactose:(glucosyl) lipopolysaccharide-alpha-1,3-D-galactosyltransferase WaaI [KO:K03275] [EC:2.4.1.-]
ECO103_4555  putative UDP-glucose: (galactosyl) LPS alpha1,2-glucosyltransferase WaaJ [KO:K03279] [EC:2.4.1.58]
ECO103_4556  waaD; lipopolysaccharide 1,2-N-acetylglucosamine transferase WaaD [KO:K00713] [EC:2.4.1.-]
ECO103_4557  waaL; lipid A-core: surface polymer ligase WaaL [KO:K02847] [EC:2.4.99.26]
Compound
C00043  UDP-N-acetyl-alpha-D-glucosamine
C00199  D-Ribulose 5-phosphate
C00229  Acyl-carrier protein
C01112  D-Arabinose 5-phosphate
C01187  3-Deoxy-D-manno-octulosonate
C04088  Octadecanoyl-[acyl-carrier protein]
C04121  CMP-3-deoxy-D-manno-octulosonate
C04478  3-Deoxy-D-manno-octulosonate 8-phosphate
C04652  UDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine
C04738  UDP-3-O-(3-hydroxytetradecanoyl)-N-acetylglucosamine
C04824  Lipid X
C04919  2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate
C04932  Lipid A disaccharide
C05223  Dodecanoyl-[acyl-carrier protein]
C05382  Sedoheptulose 7-phosphate
C05761  Tetradecanoyl-[acp]
C06022  UDP-3-O-(3-hydroxytetradecanoyl)-D-glucosamine
C06024  3-Deoxy-D-manno-octulosonyl-lipid IV(A)
C06025  KDO2-lipid IVA
C06026  KDO2-lipid A
C06251  Lauroyl-KDO2-lipid IV(A)
C06397  ADP-D-glycero-beta-D-manno-heptose
C06398  ADP-L-glycero-beta-D-manno-heptose
C07836  D-glycero-beta-D-manno-Heptose 7-phosphate
C07838  D-glycero-beta-D-manno-Heptose 1-phosphate
C11472  D-glycero-beta-D-manno-Heptose 1,7-bisphosphate
C19877  4-O-Phospho-alpha-Kdo-(2->6)-lipid IVA
C19878  D-glycero-alpha-D-manno-Heptose 7-phosphate
C19879  D-glycero-alpha-D-manno-Heptose 1,7-bisphosphate
C19880  D-glycero-alpha-D-manno-Heptose 1-phosphate
C19881  GDP-D-glycero-alpha-D-manno-heptose
C19884  Lipid IIA
C19890  alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A
C20933  (9Z)-Hexadec-9-enoyl-KDO2-lipid IV(A)
C21157  KDO2-lipid A 1-diphosphate
C21173  PEtN-KDO2-lipid A
C21461  KDO2-lipid A 1-(2-aminoethyl diphosphate)
C21463  KDO2-lipid A 1,4'-bis(2-aminoethyl diphosphate)
C21982  Lipid IVB
C21983  Deacyl-lipid IVB
C21984  Deacyl-lipid IVA
C21988  H. pylori KDO2-lipid A
C21991  Palmitoleoyl-myristoyl-KDO2-lipid A
C21992  3'-O-Deacylated KDO2-lipid A
C21993  C16-KDO2-lipid A
C21994  1-Dephospho-KDO2-lipid A
C21995  1-PEtN-KDO2-lipid A
C21996  1-PEtN-KDO-lipid A
C21997  4'-Dephosphorylated 1-PEtN-KDO-lipid A
C21998  H. pylori KDO-lipid A
C21999  Stearoyl-KDO2-lipid IVA
C22002  Lipid IIB
C22003  (S)-2-Hydroxymyristate-modified lipid A
C22068  H. pylori KDO2-lipid IVA
Reference
PMID:9791168
  Authors
Heinrichs DE, Yethon JA, Whitfield C.
  Title
Molecular basis for structural diversity in the core regions of the lipopolysaccharides of Escherichia coli and Salmonella enterica.
  Journal
Mol Microbiol 30:221-32 (1998)
DOI:10.1046/j.1365-2958.1998.01063.x
Reference
  Authors
Kneidinger B, Marolda C, Graninger M, Zamyatina A, McArthur F, Kosma P, Valvano MA, Messner P.
  Title
Biosynthesis pathway of ADP-L-glycero-beta-D-manno-heptose in Escherichia coli.
  Journal
J Bacteriol 184:363-9 (2002)
DOI:10.1128/JB.184.2.363-369.2002
Reference
PMID:9587193
  Authors
Wyckoff TJ, Raetz CR, Jackman JE.
  Title
Antibacterial and anti-inflammatory agents that target endotoxin.
  Journal
Trends Microbiol 6:154-9 (1998)
DOI:10.1016/S0966-842X(98)01230-X
Reference
PMID:9765561
  Authors
Shibayama K, Ohsuka S, Tanaka T, Arakawa Y, Ohta M.
  Title
Conserved structural regions involved in the catalytic mechanism of Escherichia coli K-12 WaaO (RfaI).
  Journal
J Bacteriol 180:5313-8 (1998)
DOI:10.1128/JB.180.20.5313-5318.1998
Reference
  Authors
Raetz CR, Whitfield C
  Title
Lipopolysaccharide endotoxins.
  Journal
Annu Rev Biochem 71:635-700 (2002)
DOI:10.1146/annurev.biochem.71.110601.135414
Reference
  Authors
Rubin EJ, O'Brien JP, Ivanov PL, Brodbelt JS, Trent MS
  Title
Identification of a broad family of lipid A late acyltransferases with non-canonical substrate specificity.
  Journal
Mol Microbiol 91:887-99 (2014)
DOI:10.1111/mmi.12501
Reference
  Authors
Stead CM, Zhao J, Raetz CR, Trent MS
  Title
Removal of the outer Kdo from Helicobacter pylori lipopolysaccharide and its impact on the bacterial surface.
  Journal
Mol Microbiol 78:837-52 (2010)
DOI:10.1111/j.1365-2958.2010.07304.x
Reference
  Authors
Ebbensgaard A, Mordhorst H, Aarestrup FM, Hansen EB
  Title
The Role of Outer Membrane Proteins and Lipopolysaccharides for the Sensitivity of Escherichia coli to Antimicrobial Peptides.
  Journal
Front Microbiol 9:2153 (2018)
DOI:10.3389/fmicb.2018.02153
Reference
  Authors
Botos I, Noinaj N, Buchanan SK
  Title
Insertion of proteins and lipopolysaccharide into the bacterial outer membrane.
  Journal
Philos Trans R Soc Lond B Biol Sci 372:20160224 (2017)
DOI:10.1098/rstb.2016.0224
Related
pathway
eoh00030  Pentose phosphate pathway
eoh00520  Amino sugar and nucleotide sugar metabolism
KO pathway
ko00540   
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