KEGG   PATHWAY: ko00540
Entry
ko00540                     Pathway                                

Name
Lipopolysaccharide biosynthesis
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
ko00540  Lipopolysaccharide biosynthesis
ko00540

Module
M00060  KDO2-lipid A biosynthesis, Raetz pathway, LpxL-LpxM type [PATH:ko00540]
M00063  CMP-KDO biosynthesis [PATH:ko00540]
M00064  ADP-L-glycero-D-manno-heptose biosynthesis [PATH:ko00540]
M00866  KDO2-lipid A biosynthesis, Raetz pathway, non-LpxL-LpxM type [PATH:ko00540]
M00867  KDO2-lipid A modification pathway [PATH:ko00540]
Other DBs
GO: 0009103
Orthology
K00677  UDP-N-acetylglucosamine acyltransferase [EC:2.3.1.129]
K02535  UDP-3-O-[3-hydroxymyristoyl] N-acetylglucosamine deacetylase [EC:3.5.1.108]
K16363  UDP-3-O-[3-hydroxymyristoyl] N-acetylglucosamine deacetylase / 3-hydroxyacyl-[acyl-carrier-protein] dehydratase [EC:3.5.1.108 4.2.1.59]
K02536  UDP-3-O-[3-hydroxymyristoyl] glucosamine N-acyltransferase [EC:2.3.1.191]
K03269  UDP-2,3-diacylglucosamine hydrolase [EC:3.6.1.54]
K00748  lipid-A-disaccharide synthase [EC:2.4.1.182]
K00912  tetraacyldisaccharide 4'-kinase [EC:2.7.1.130]
K06041  arabinose-5-phosphate isomerase [EC:5.3.1.13]
K01627  2-dehydro-3-deoxyphosphooctonate aldolase (KDO 8-P synthase) [EC:2.5.1.55]
K03270  3-deoxy-D-manno-octulosonate 8-phosphate phosphatase (KDO 8-P phosphatase) [EC:3.1.3.45]
K00979  3-deoxy-manno-octulosonate cytidylyltransferase (CMP-KDO synthetase) [EC:2.7.7.38]
K02527  3-deoxy-D-manno-octulosonic-acid transferase [EC:2.4.99.12 2.4.99.13 2.4.99.14 2.4.99.15]
K02517  Kdo2-lipid IVA lauroyltransferase/acyltransferase [EC:2.3.1.241 2.3.1.-]
K02560  lauroyl-Kdo2-lipid IVA myristoyltransferase [EC:2.3.1.243]
K12979  beta-hydroxylase [EC:1.14.11.-]
K09953  lipid A 3-O-deacylase [EC:3.1.1.-]
K19803  Kdo2-lipid A phosphotransferase [EC:2.7.4.29]
K03760  lipid A ethanolaminephosphotransferase [EC:2.7.8.43]
K12975  KDO II ethanolaminephosphotransferase [EC:2.7.8.42]
K12973  lipid IVA palmitoyltransferase [EC:2.3.1.251]
K07264  4-amino-4-deoxy-L-arabinose transferase [EC:2.4.2.43]
K12976  lipid A 3-O-deacylase [EC:3.1.1.-]
K09778  Kdo2-lipid IVA 3' secondary acyltransferase [EC:2.3.1.-]
K12977  lipid A 1-phosphatase [EC:3.1.3.-]
K23082  3-deoxy-D-manno-octulosonic acid-hydrolase [EC:3.2.1.144]
K23083  3-deoxy-D-manno-octulosonic acid-hydrolase
K23159  lipid A 4'-phosphatase [EC:3.1.3.-]
K11211  3-deoxy-D-manno-octulosonic acid kinase [EC:2.7.1.166]
K12974  KDO2-lipid IV(A) palmitoleoyltransferase [EC:2.3.1.242]
K03271  D-sedoheptulose 7-phosphate isomerase [EC:5.3.1.28]
K03272  D-beta-D-heptose 7-phosphate kinase / D-beta-D-heptose 1-phosphate adenosyltransferase [EC:2.7.1.167 2.7.7.70]
K21344  D-glycero-beta-D-manno-heptose-7-phosphate kinase [EC:2.7.1.167]
K03273  D-glycero-D-manno-heptose 1,7-bisphosphate phosphatase [EC:3.1.3.82 3.1.3.83]
K21345  D-glycero-beta-D-manno-heptose 1-phosphate adenylyltransferase [EC:2.7.7.70]
K03274  ADP-L-glycero-D-manno-heptose 6-epimerase [EC:5.1.3.20]
K07031  D-glycero-alpha-D-manno-heptose-7-phosphate kinase [EC:2.7.1.168]
K15669  D-glycero-alpha-D-manno-heptose 1-phosphate guanylyltransferase [EC:2.7.7.71]
K02841  heptosyltransferase I [EC:2.4.-.-]
K02843  heptosyltransferase II [EC:2.4.-.-]
K02848  heptose I phosphotransferase [EC:2.7.1.-]
K19353  heptose-I-phosphate ethanolaminephosphotransferase [EC:2.7.8.-]
K02849  heptosyltransferase III [EC:2.4.-.-]
K23160  GlcNAc transferase
K02850  heptose II phosphotransferase [EC:2.7.1.-]
K12981  KDO transferase III [EC:2.4.99.-]
K12986  1,5-rhamnosyltransferase [EC:2.4.1.-]
K02844  UDP-glucose:(heptosyl)LPS alpha-1,3-glucosyltransferase [EC:2.4.1.-]
K02840  UDP-D-galactose:(glucosyl)LPS alpha-1,6-D-galactosyltransferase [EC:2.4.1.-]
K03275  UDP-glucose:(glucosyl)LPS alpha-1,3-glucosyltransferase [EC:2.4.1.-]
K03276  UDP-glucose/galactose:(glucosyl)LPS alpha-1,2-glucosyl/galactosyltransferase [EC:2.4.1.-]
K03277  heptosyltransferase IV [EC:2.4.-.-]
K12983  UDP-glucose:(glucosyl)LPS beta-1,3-glucosyltransferase [EC:2.4.1.-]
K12985  (galactosyl)LPS 1,2-glucosyltransferase [EC:2.4.1.-]
K03280  UDP-N-acetylglucosamine:(glucosyl)LPS alpha-1,2-N-acetylglucosaminyltransferase [EC:2.4.1.56]
K03278  UDP-D-galactose:(glucosyl)LPS alpha-1,3-D-galactosyltransferase [EC:2.4.1.44]
K03279  UDP-glucose:(galactosyl)LPS alpha-1,2-glucosyltransferase [EC:2.4.1.58]
K00713  UDP-glucose:(glucosyl)LPS alpha-1,2-glucosyltransferase [EC:2.4.1.-]
K23067  beta-1,4-galactosyltransferase
K02847  O-antigen ligase [EC:2.4.1.-]
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
ko00030  Pentose phosphate pathway
ko00520  Amino sugar and nucleotide sugar metabolism
LinkDB

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