KEGG   PATHWAY: rn00541
Entry
rn00541                     Pathway                                
Name
O-Antigen nucleotide sugar biosynthesis
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
rn00541  O-Antigen nucleotide sugar biosynthesis
rn00541

Module
M00793  dTDP-L-rhamnose biosynthesis [PATH:rn00541]
M00922  CMP-Neu5Ac biosynthesis [PATH:rn00541]
M00923  UDP-L-FucNAm biosynthesis [PATH:rn00541]
Reaction
R00286  UDP-glucose:NAD+ 6-oxidoreductase
R00289  UTP:alpha-D-glucose-1-phosphate uridylyltransferase
R00291  UDP-glucose 4-epimerase
R00414  UDP-N-acetyl-D-glucosamine 2-epimerase
R00416  UTP:N-acetyl-alpha-D-glucosamine-1-phosphate uridylyltransferase
R00418  UDP-N-acetyl-D-glucosamine 4-epimerase
R00420  UDP-N-acetyl-D-glucosamine 2-epimerase
R00421  UDP-N-acetyl-D-glucosamine:NAD+ 6-oxidoreductase
R00505  UDP-alpha-D-galactopyranose furanomutase
R00885  GTP:alpha-D-mannose-1-phosphate guanylyltransferase
R00888  GDP-alpha-D-mannose 4,6-hydro-lyase (GDP-4-dehydro-alpha-D-rhamnose-forming)
R00956  CTP:alpha-D-glucose-1-phosphate cytidylyltransferase
R01117  CTP:N-acetylneuraminate cytidylyltransferase
R01385  UDP-glucuronate 4-epimerase
R01387  UDP-glucuronate 5'-epimerase
R01804  phosphoenolpyruvate:N-acetyl-D-mannosamine C-(1-carboxyvinyl)transferase (phosphate-hydrolysing, 2-carboxy-2-oxoethyl-forming)
R01818  D-mannose 6-phosphate 1,6-phosphomutase
R01819  D-mannose-6-phosphate aldose-ketose-isomerase
R02328  dTTP:alpha-D-glucose-1-phosphate thymidylyltransferase
R02426  CDPglucose 4,6-hydro-lyase
R02773  dTDP-4-amino-4,6-dideoxy-D-glucose:2-oxoglutarate aminotransferase
R02776  dTDP-6-deoxy-L-talose:NADP+ 4-oxidoreductase
R02777  dTDP-beta-L-rhamnose:NADP+ 4-oxidoreductase
R03317  UDP-N-acetyl-alpha-D-mannosamine:NAD+ 6-oxidoreductase
R03391  CDP-4-dehydro-3,6-dideoxy-D-glucose:NAD+ 3-oxydoreductase
R03392  CDP-4-dehydro-3,6-dideoxy-D-glucose:NADP+ 3-oxydoreductase
R03396  GDP-6-deoxy-D-talose:NAD+ 4-oxidoreductase
R03397  GDP-6-deoxy-D-mannose:NAD+ 4-oxidoreductase
R03398  GDP-6-deoxy-D-talose:NADP+ 4-oxidoreductase
R03399  GDP-6-deoxy-D-mannose:NADP+ 4-oxidoreductase
R04265  CDP-alpha-D-paratose:NADP+ 4-oxidoreductase
R04266  CDP-3,6-dideoxy-D-glucose 2-epimerase
R04438  dTDP-4-amino-4,6-dideoxy-D-galactose:2-oxoglutarate aminotransferase
R04529  UDP-4-amino-4,6-dideoxy-N-acetyl-alpha-D-glucosamine:2-oxoglutarate aminotransferase
R05687  dTDP-4-keto-6-Deoxyglucose reductase
R05692  GDP-L-fucose:NADP+ 4-oxidoreductase (3,5-epimerizing)
R06423  dTDP-3-amino-3,6-dideoxy-alpha-D-glucopyranose:2-oxoglutarate aminotransferase
R06424  dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose:dTDP-3-dehydro-6-deoxy-alpha-D-glucopyranose isomerase
R06513  dTDPglucose 4,6-hydro-lyase
R06514  dTDP-4-dehydro-6-deoxy-alpha-D-glucose 3,5-epimerase
R06894   
R08706  UDP-N-acetyl-D-glucosaminuronate 4-epimerase
R08708  CDP-4-dehydro-3,6-dideoxy-D-glucose 5-epimerase
R08709  CDP-ascarylose:NAD+ 4-oxidoreductase
R08710  CDP-ascarylose:NADP+ 4-oxidoreductase
R08711  CDP-abequose:NADP+ 4-oxidoreductase
R09600  2,3-diacetamido-2,3-dideoxy-alpha-D-glucuronate 2-epimerase
R09697  UDP-N-acetylglucosamine hydro-lyase (inverting; UDP-2-acetamido-2,6-dideoxy-beta-L-arabino-hexos-4-ulose-forming)
R09824  dTDP-3-amino-3,6-dideoxy-alpha-D-galactopyranose:2-oxoglutarate aminotransferase
R09825  UDP-4-amino-4,6-dideoxy-N-acetyl-beta-L-altrosamine:2-oxoglutarate aminotransferase
R09834  UDP-2,4-bis(acetamido)-2,4,6-trideoxy-beta-L-altropyranose hydrolase
R09841  phosphoenolpyruvate:2,4-bis(acetylamino)-2,4,6-trideoxy-beta-L-altropyranose transferase (phosphate-hydrolysing, 2,7-acetylamino-transfering, 2-carboxy-2-oxoethyl-forming)
R09842  acetyl-CoA:UDP-4-amino-4,6-dideoxy-N-acetyl-beta-L-altrosamine 4-N-acetyltransferase
R09843  CTP:pseudaminate cytidylyltransferase
R09873  acetyl-CoA:dTDP-3-amino-3,6-dideoxy-alpha-D-galactopyranose 3-N-acetyltransferase
R09904  dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose:dTDP-3-dehydro-6-deoxy-alpha-D-galactopyranose isomerase
R10100  acetyl-CoA:UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucuronate 3-N-acetyltransferase
R10140  UDP-N-acetyl-2-amino-2-deoxy-alpha-D-glucuronate:NAD+ 3-oxidoreductase
R10141  UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucuronate:2-oxoglutarate aminotransferase
R10142  acetyl-CoA:dTDP-4-amino-4,6-dideoxy-alpha-D-galactose N-acetyltransferase
R10174  acetyl-CoA:dTDP-4-amino-4,6-dideoxy-alpha-D-glucose N-acetyltransferase
R10190  dTDP-6-deoxy-beta-L-talose:NAD+ 4-oxidoreductase
R10266  UDP-N-acetyl-alpha-D-glucosamine hydro-lyase
R10420  GDP-beta-L-colitose:NAD+ 4-oxidoreductase (5-epimerizing)
R10421  GDP-beta-L-colitose:NADP+ 4-oxidoreductase (5-epimerizing)
R10460  GDP-4-amino-4,6-dideoxy-alpha-D-mannose:2-oxoglutarate aminotransferase
R10514  acetyl-CoA:GDP-4-amino-4,6-dideoxy-alpha-D-mannose N-acetyltransferase
R10536  dTDP-alpha-D-fucopyranose furanomutase
R10676  UDP-2-acetamido-2,6-dideoxy-beta-L-talose 2-epimerase
R11409  GDP-4-dehydro-alpha-D-rhamnose 3-hydro-lyase
R12549   
R12551   
R12552   
R12553   
R12554   
R12555   
R12556  UDP-N-acetyl-alpha-D-quinovosamine:NADP+ 4-dehydrogenase
R12557   
R12558   
R12559   
R12561   
R12562   
R12563   
R12564   
R12565   
R12567   
R12568   
R12584   
R12586   
R12590   
R12604   
R12606   
R12760  UDP-N-acetyl-alpha-D-quinovosamine:NAD+ 4-dehydrogenase
R12790  10-formyltetrahydrofolate:GDP-alpha-D-perosamine N-formyltransferase
Compound
C00029  UDP-glucose
C00043  UDP-N-acetyl-alpha-D-glucosamine
C00052  UDP-alpha-D-galactose
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
C05345  beta-D-Fructose 6-phosphate
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
Reference
  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
  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
  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
  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
  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
  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
  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
  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
  Authors
McDonald ND, DeMeester KE, Lewis AL, Grimes CL, Boyd EF
  Title
Structural and functional characterization of a modified legionaminic acid involved in glycosylation of a bacterial lipopolysaccharide.
  Journal
J Biol Chem 293:19113-19126 (2018)
DOI:10.1074/jbc.RA118.004966
Related
pathway
rn00520  Amino sugar and nucleotide sugar metabolism
KO pathway
ko00541   
LinkDB

DBGET integrated database retrieval system