Entry 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 rn00540 Lipopolysaccharide biosynthesis
Ortholog table Module M00060 KDO2-lipid A biosynthesis, Raetz pathway, LpxL-LpxM type [PATH:rn00540 ]
M00866 KDO2-lipid A biosynthesis, Raetz pathway, non-LpxL-LpxM type [PATH:rn00540 ]
Other DBs Reaction R01530 D-arabinose-5-phosphate aldose-ketose-isomerase
R03254 phosphoenolpyruvate:D-arabinose-5-phosphate C-(1-carboxyvinyl)transferase (phosphate-hydrolysing, 2-carboxy-2-oxoethyl-forming)
R03350 3-deoxy-D-manno-octulosonate-8-phosphate 8-phosphohydrolase
R03351 CTP:3-deoxy-D-manno-octulosonate cytidylyltransferase
R04549 UDP-2,3-bis[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine 2,3-bis[(3R)-3-hydroxymyristoyl]-beta-D-glucosaminyl 1-phosphate phosphohydrolase
R04550 (3R)-3-hydroxymyristoyl-[acyl-carrier protein]:UDP-3-O-[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine N-acetyltransferase
R04567 (R)-3-hydroxytetradecanoly-[acyl-carrier-protein]:UDP-N-acetyl-glucosamine 3-O-(3-hydroxytetradecanoyl)transferase
R04587 UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetylglucosamine amidohydrolase
R04606 UDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine:2,3-bis-(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl-1-phosphate 2,3-bis(3-hydroxytetradecanoyl)-glucosaminyltransferase
R04657 ATP:2,3,2',3'-tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-beta-D-1,6-glucosaminyl-alpha-phosphate 4-O'-phosphotransferase
R04658 CMP-3-deoxy-D-manno-oct-2-ulosonate:lipid IVA 3-deoxy-D-manno-oct-2-ulosonate transferase
R05074 CMP-3-deoxy-D-manno-oct-2-ulosonate:(KDO)-lipid IVA 3-deoxy-D-manno-oct-2-ulosonate transferase
R05075 tetradecanoyl-[acyl-carrier protein]:dodecanoyl-KDO2-lipid IV(A) O-tetradecanoyltransferase
R05146 dodecanoyl-[acyl-carrier protein]:KDO2-lipid-IVA O-dodecanoyltransferase
R05176 ADP-D-glycero-D-manno-heptose 6-epimerase
R05644 ATP:D-glycero-beta-D-manno-heptose 1-phosphate adenylyltransferase
R05645 D-glycero-beta-D-manno-heptose-7-phosphate aldose-ketose-isomerase
R05646 ATP:D-glycero-beta-D-manno-heptose 7-phosphate 1-phosphotransferase
R05647 D-glycero-beta-D-manno-heptose 1,7-bisphosphate 7-phosphohydrolase
R09767 ATP:(KDO)-lipid IVA 3-deoxy-alpha-D-manno-oct-2-ulopyranose 4-phosphotransferase
R09769 D-glycero-alpha-D-manno-heptose 7-phosphate aldose-ketose-isomerase
R09770 ATP:D-glycero-alpha-D-manno-heptose 7-phosphate 1-phosphotransferase
R09771 D-glycero-alpha-D-manno-heptose 1,7-bisphosphate 7-phosphohydrolase
R09772 GTP:D-glycero-alpha-D-manno-heptose 1-phosphate guanylyltransferase
R09773 4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate:lipid IVA 4-amino-4-deoxy-beta-L-arabinopyranosyltransferase
R09781 4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate:KDO2-lipid A 4-amino-4-deoxy-alpha-L-arabinopyranosyltransferase
R10906 (9Z)-hexadec-9-enoyl-[acyl-carrier protein]:KDO2-lipid IVA O-palmitoleoyltransferase
R11186 ditrans,octacis-undecaprenyl-diphosphate:KDO2-lipid-A phosphotransferase
R11204 phosphatidylethanolamine:KDO2-lipid-A 7''-O-ethanolaminephosphotransferase
R11555 phosphatidylethanolamine:KDO2-lipid-A ethanolaminephosphotransferase
R11557 phosphatidylethanolamine:KDO2-lipid-A-1-(2-aminoethyl diphosphate) ethanolaminephosphotransferase
R12187 1-palmitoyl-2-acyl-sn-glycero-3-phosphocholine:lipid-IVA palmitoyltransferase
R12193 octadecanoyl-[acyl-carrier protein]:KDO2-lipid-IVA O-octadecanoyltransferase
R12194 tetradecanoyl-[acyl-carrier protein]:octadecanoyl-KDO2-lipid-IVA O-tetradecanoyltransferase
R12196 KDO2-lipid-A acyloxyacylhydrolase
R12197 tetradecanoyl-[acyl-carrier protein]:(9Z)-hexadec-9-enoyl-KDO2-lipid IVA O-tetradecanoyltransferase
R12198 lipid-IVB hydroxyacylhydrolase
R12199 lipid-IVA hydroxyacylhydrolase
R12200 1-palmitoyl-2-acyl-sn-glycero-3-phosphocholine:deacyl-lipid-IVA palmitoyltransferase
R12201 hexa-acylated-KDO2-lipid-A phosphohydrolase
R12202 phosphatidylethanolamine:1-dephospho-KDO2-lipid-A ethanolaminephosphotransferase
R12203 1-PEtN-KDO-lipid-A phosphohydrolase
R12204 4'-dephosphorylated-1-PEtN-KDO-lipid-A acyloxyacylhydrolase
R12206 1-palmitoyl-2-acyl-sn-glycero-3-phosphocholine:lipid-IIA palmitoyltransferase
R12207 4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate:lipid IVB 4-amino-4-deoxy-L-arabinopyranosyltransferase
R12210 KDO2-lipid-A,2-oxoglutarate:oxygen oxidoreductase (ester-linked acyl 2-hydroxylase)
R12211 1-palmitoyl-2-acyl-sn-glycero-3-phosphocholine:KDO2-lipid-A palmitoyltransferase
R12219 KDO2-lipid-A-1-(2-aminoethyl phosphate) hydrolase
Compound C00043 UDP-N-acetyl-alpha-D-glucosamine
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
C04919 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate
C05223 Dodecanoyl-[acyl-carrier protein]
C05382 Sedoheptulose 7-phosphate
C06022 UDP-3-O-(3-hydroxytetradecanoyl)-D-glucosamine
C06024 3-Deoxy-D-manno-octulosonyl-lipid IV(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
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
C21461 KDO2-lipid A 1-(2-aminoethyl diphosphate)
C21463 KDO2-lipid A 1,4'-bis(2-aminoethyl diphosphate)
C21991 Palmitoleoyl-myristoyl-KDO2-lipid A
C21992 3'-O-Deacylated KDO2-lipid A
C21994 1-Dephospho-KDO2-lipid A
C21997 4'-Dephosphorylated 1-PEtN-KDO-lipid A
C21999 Stearoyl-KDO2-lipid IVA
C22003 (S)-2-Hydroxymyristate-modified lipid A
C22068 H. pylori KDO2-lipid IVA
Reference 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 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 Reference Authors Wyckoff TJ, Raetz CR, Jackman JE.
Title Antibacterial and anti-inflammatory agents that target endotoxin.
Journal Reference 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 Reference Authors Raetz CR, Whitfield C
Title Lipopolysaccharide endotoxins.
Journal 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 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 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 Reference Authors Botos I, Noinaj N, Buchanan SK
Title Insertion of proteins and lipopolysaccharide into the bacterial outer membrane.
Journal Related rn00520 Amino sugar and nucleotide sugar metabolism
KO pathway LinkDB All DBs
