KEGG PATHWAY: esm00541

PATHWAY: esm00541

Entry

esm00541                    Pathway

Name

O-Antigen nucleotide sugar biosynthesis - Escherichia coli O104:H4 2009EL-2050 (EAEC)

Description

The O-antigen is a repetitive glycan polymer with a repeat unit of two to six sugar residues, and comprises the outermost and immunogenic domain of the lipopolysaccharide (map00540). Most of the sugar residues are derived from nucleotide sugars and the genes for their biosynthesis seem to be well conserved among Gram-negative bacterial species. They include UDP-sugars synthesized from Glc-1P via UDP-Glc or from GlcNAc-1P via UDP-GlcNAc, GDP-sugars synthesized from Fru-6P via GDP-Man, and dTDP-sugars and CDP-sugars synthesized from Glc-1P via dTDP-Glc and CDP-Glc, respectively. CMP-sugars are also synthesized from UDP-GlcNAc. The O-antigen nucleotide sugar biosynthesis genes often form gene clusters with glycosyltransferase genes and other processing genes such as for translocation and polymerization.

Class

Metabolism; Glycan biosynthesis and metabolism

Pathway map

esm00541

O-Antigen nucleotide sugar biosynthesis

Module

esm_M00922

CMP-Neu5Ac biosynthesis [PATH:esm00541]

Organism

Escherichia coli O104:H4 2009EL-2050 (EAEC) [GN:esm]

Gene

O3M_14450

UTP--glucose-1-phosphate uridylyltransferase subunit GalU [KO:K00963] [EC:2.7.7.9]

O3M_09185

GalU regulator GalF [KO:K00963] [EC:2.7.7.9]

O3M_17855

UDP-galactose-4-epimerase [KO:K01784] [EC:5.1.3.2]

O3M_09240

UDP-glucose 6-dehydrogenase [KO:K00012] [EC:1.1.1.22]

O3M_24840

glucose-1-phosphate thymidylyltransferase [KO:K00973] [EC:2.7.7.24]

O3M_24845

dTDP-glucose 4,6-dehydratase [KO:K01710] [EC:4.2.1.46]

O3M_24830

TDP-4-oxo-6-deoxy-D-glucose transaminase [KO:K02805] [EC:2.6.1.59]

O3M_24835

TDP-fucosamine acetyltransferase [KO:K16704] [EC:2.3.1.210]

O3M_12135

mannose-6-phosphate isomerase [KO:K01809] [EC:5.3.1.8]

O3M_09150

phosphomannomutase CpsG [KO:K01840] [EC:5.4.2.8]

O3M_09145

cpsB; mannose-1-phosphate guanyltransferase [KO:K00971] [EC:2.7.7.13]

O3M_09125

GDP-mannose 4,6-dehydratase [KO:K01711] [EC:4.2.1.47]

O3M_09130

bifunctional GDP-fucose synthetase: GDP-4-dehydro-6-deoxy-D-mannose epimerase and GDP-4-dehydro-6-L-deoxygalactose reductase [KO:K02377] [EC:1.1.1.271]

O3M_25090

glmU; bifunctional N-acetylglucosamine-1-phosphate uridyltransferase/glucosamine-1-phosphate acetyltransferase [KO:K04042] [EC:2.7.7.23 2.3.1.157]

O3M_24855

UDP-N-acetylglucosamine 2-epimerase [KO:K01791] [EC:5.1.3.14]

O3M_24850

wecC; UDP-N-acetyl-D-mannosamine dehydrogenase [KO:K02472] [EC:1.1.1.336]

O3M_09205

NnaA [KO:K24257] [EC:3.2.1.183]

O3M_09195

NnaB [KO:K01654] [EC:2.5.1.56]

O3M_09200

N-acylneuraminate cytidylyltransferase [KO:K00983] [EC:2.7.7.43]

Compound

C00029

UDP-glucose

C00043

UDP-N-acetyl-alpha-D-glucosamine

C00052

UDP-alpha-D-galactose

C00085

D-Fructose 6-phosphate

C00096

GDP-mannose

C00103

D-Glucose 1-phosphate

C00128

CMP-N-acetylneuraminate

C00167

UDP-glucuronate

C00203

UDP-N-acetyl-D-galactosamine

C00270

N-Acetylneuraminate

C00275

D-Mannose 6-phosphate

C00325

GDP-L-fucose

C00501

CDP-glucose

C00617

UDP-D-galacturonate

C00636

D-Mannose 1-phosphate

C00645

N-Acetyl-D-mannosamine

C00688

dTDP-4-dehydro-beta-L-rhamnose

C00842

dTDP-glucose

C01170

UDP-N-acetyl-D-mannosamine

C01219

CDP-4-dehydro-6-deoxy-D-glucose

C01222

GDP-4-dehydro-6-deoxy-D-mannose

C01788

CDP-abequose

C02330

UDP-L-iduronate

C02977

GDP-6-deoxy-D-talose

C03117

GDP-6-deoxy-D-mannose

C03187

dTDP-6-deoxy-beta-L-talose

C03319

dTDP-L-rhamnose

C03598

CDP-3,6-dideoxy-D-glucose

C03599

CDP-3,6-dideoxy-D-mannose

C03733

UDP-alpha-D-galactofuranose

C04268

dTDP-4-amino-4,6-dideoxy-D-glucose

C04297

CDP-4-dehydro-3,6-dideoxy-D-glucose

C04346

dTDP-4-amino-4,6-dideoxy-D-galactose

C04501

N-Acetyl-alpha-D-glucosamine 1-phosphate

C04573

UDP-N-acetyl-2-amino-2-deoxy-D-glucuronate

C04613

UDP-2-acetamido-4-dehydro-2,6-dideoxyglucose

C04630

UDP-2-acetamido-4-amino-2,4,6-trideoxy-alpha-D-glucose

C06018

dTDP-4-acetamido-4,6-dideoxy-D-glucose

C06240

UDP-N-acetyl-D-mannosaminouronate

C07277

dTDP-D-fucose

C11907

dTDP-4-oxo-6-deoxy-D-glucose

C11908

3,6-Dideoxy-3-oxo-dTDP-D-glucose

C11925

dTDP-3-amino-3,6-dideoxy-D-glucose

C13952

UDP-N-acetyl-D-galactosaminuronic acid

C17326

CDP-4-dehydro-3,6-dideoxy-D-glucose epimer

C17327

CDP-ascarylose

C19725

UDP-2,3-diacetamido-2,3-dideoxy-alpha-D-glucuronate

C19745

UDP-2,3-diacetamido-2,3-dideoxy-alpha-D-mannuronate

C19823

UDP-2-acetamido-2,6-dideoxy-beta-L-arabino-hexos-4-ulose

C19947

dTDP-3-amino-3,6-dideoxy-alpha-D-galactopyranose

C19960

dTDP-3-dehydro-6-deoxy-alpha-D-galactopyranose

C19961

UDP-4-amino-4,6-dideoxy-N-acetyl-beta-L-altrosamine

C19971

UDP-2,4-bis(acetamido)-2,4,6-trideoxy-beta-L-altropyranose

C19972

2,4-Bis(acetamido)-2,4,6-trideoxy-beta-L-altropyranose

C20082

Pseudaminic acid

C20083

CMP-pseudaminic acid

C20156

dTDP-3-acetamido-3,6-dideoxy-alpha-D-galactopyranose

C20359

UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucuronate

C20395

UDP-2-acetamido-2-deoxy-alpha-D-ribo-hex-3-uluronate

C20415

dTDP-4-acetamido-4,6-dideoxy-alpha-D-galactose

C20612

GDP-4-dehydro-3,6-dideoxy-alpha-D-mannose

C20613

GDP-beta-L-colitose

C20638

GDP-4-amino-4,6-dideoxy-alpha-D-mannose

C20672

GDP-4-acetamido-4,6-dideoxy-alpha-D-mannose

C20682

dTDP-alpha-D-fucofuranose

C20768

UDP-2-acetamido-2,6-dideoxy-beta-L-talose

C20769

UDP-2-acetamido-2,6-dideoxy-beta-L-lyxo-4-hexulose

C20774

UDP-N-acetyl-beta-L-fucosamine

C22245

UDP-2-acetamido-2-deoxy-alpha-D-galacturonamide

C22246

UDP-2,3-dideoxy-2-acetamido-3-acetamidino-alpha-D-mannuronic acid

C22247

UDP-2-acetamido-4-(D-alanylamino)-2,4,6-trideoxy-alpha-D-glucopyranose

C22248

UDP-2-acetamido-4-(D-alanylamino)-2,4,6-trideoxy-alpha-D-mannopyranose

C22249

2-Acetamido-4-(D-alanylamino)-2,4,6-trideoxy-D-mannopyranose

C22250

5-N-Acetyl-7-N-(D-alanyl)-legionaminic acid

C22251

CMP-5-N-acetyl-7-N-(D-alanyl)-legionaminic acid

C22252

UDP-2,4-diacetamido-2,4,6-trideoxy-beta-L-idose

C22253

UDP-2,4-diacetamido-2,4,6-trideoxy-beta-L-gulose

C22254

2,4-Diacetamido-2,4,6-trideoxy-beta-L-gulose

C22255

5,7-Diacetamido-3,5,7,9-tetradeoxy-L-glycero-D-galacto-non-2-ulosonic acid

C22256

CMP-5,7-diacetamido-3,5,7,9-tetradeoxy-L-glycero-D-galacto-non-2-ulosonic acid

C22257

dTDP-3-acetamido-3,6-dideoxy-alpha-D-glucose

C22259

UDP-2-acetamido-2,6-dideoxy-beta-L-mannose

C22260

UDP-2-acetamido-2,6-dideoxy-beta-L-glucose

C22261

UDP-2-acetamido-2,6-dideoxy-alpha-D-galactose

C22262

UDP-2-acetamido-2,6-dideoxy-alpha-D-glucose

C22270

UDP-2,6-dideoxy-2-acetamidino-beta-L-galactose

C22276

UDP-4-amino-4,6-dideoxy-N-acetyl-beta-L-idosamine

C22397

GDP-N-formyl-alpha-D-perosamine

C22575

UDP-2-acetamido-4-amino-2,4,6-trideoxy-D-galactose

C22576

UDP-2-acetamido-2-deoxy-L-altruronic acid

Reference

PMID:14670712

Authors

Samuel G, Reeves P

Title

Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly.

Journal

Carbohydr Res 338:2503-19 (2003)
DOI:10.1016/j.carres.2003.07.009

Reference

PMID:8939432

Authors

Burrows LL, Charter DF, Lam JS

Title

Molecular characterization of the Pseudomonas aeruginosa serotype O5 (PAO1) B-band lipopolysaccharide gene cluster.

Journal

Mol Microbiol 22:481-95 (1996)
DOI:10.1046/j.1365-2958.1996.1351503.x

Reference

PMID:10627048

Authors

Belanger M, Burrows LL, Lam JS

Title

Functional analysis of genes responsible for the synthesis of the B-band O antigen of Pseudomonas aeruginosa serotype O6 lipopolysaccharide.

Journal

Microbiology 145 ( Pt 12):3505-21 (1999)
DOI:10.1099/00221287-145-12-3505

Reference

PMID:10828401

Authors

Dean CR, Goldberg JB

Title

The wbpM gene in Pseudomonas aeruginosa serogroup O17 resides on a cryptic copy of the serogroup O11 O antigen gene locus.

Journal

FEMS Microbiol Lett 187:59-63 (2000)
DOI:10.1111/j.1574-6968.2000.tb09137.x

Reference

PMID:15629947

Authors

Feng L, Senchenkova SN, Tao J, Shashkov AS, Liu B, Shevelev SD, Reeves PR, Xu J, Knirel YA, Wang L

Title

Structural and genetic characterization of enterohemorrhagic Escherichia coli O145 O antigen and development of an O145 serogroup-specific PCR assay.

Journal

J Bacteriol 187:758-64 (2005)
DOI:10.1128/JB.187.2.758-764.2005

Reference

PMID:18621892

Authors

Westman EL, Preston A, Field RA, Lam JS

Title

Biosynthesis of a rare di-N-acetylated sugar in the lipopolysaccharides of both Pseudomonas aeruginosa and Bordetella pertussis occurs via an identical scheme despite different gene clusters.

Journal

J Bacteriol 190:6060-9 (2008)
DOI:10.1128/JB.00579-08

Reference

PMID:19710102

Authors

King JD, Kocincova D, Westman EL, Lam JS

Title

Review: Lipopolysaccharide biosynthesis in Pseudomonas aeruginosa.

Journal

Innate Immun 15:261-312 (2009)
DOI:10.1177/1753425909106436

Reference

PMID:20331420

Authors

Perepelov AV, Liu B, Senchenkova SN, Shashkov AS, Shevelev SD, Feng L, Wang L, Knirel YA

Title

Structure of the O-antigen and characterization of the O-antigen gene cluster of Escherichia coli O108 containing 5,7-diacetamido-3,5,7,9-tetradeoxy-L-glycero-D-galacto-non-2-ulosonic (8-epilegionaminic) acid.

Journal

Biochemistry (Mosc) 75:19-24 (2010)
DOI:10.1134/s0006297910010037

Reference

PMID:26207987

Authors

Hwang S, Aronov A, Bar-Peled M

Title

The Biosynthesis of UDP-D-QuiNAc in Bacillus cereus ATCC 14579.

Journal

PLoS One 10:e0133790 (2015)
DOI:10.1371/journal.pone.0133790

Reference

PMID:30315110