KEGG   PATHWAY: csr00541
Entry
csr00541                    Pathway                                
Name
O-Antigen nucleotide sugar biosynthesis - Clostridium saccharoperbutylacetonicum
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
csr00541  O-Antigen nucleotide sugar biosynthesis
csr00541

Module
csr_M00793  dTDP-L-rhamnose biosynthesis [PATH:csr00541]
Organism
Clostridium saccharoperbutylacetonicum [GN:csr]
Gene
Cspa_c53460  gtaB; UTP--glucose-1-phosphate uridylyltransferase GtaB [KO:K00963] [EC:2.7.7.9]
Cspa_c12190  galU; UTP-glucose-1-phosphate uridylyltransferase GalU [KO:K00963] [EC:2.7.7.9]
Cspa_c40170  galE1; UDP-glucose 4-epimerase GalE [KO:K01784] [EC:5.1.3.2]
Cspa_c53510  galE3; UDP-glucose 4-epimerase GalE [KO:K01784] [EC:5.1.3.2]
Cspa_c46550  galE2; UDP-glucose 4-epimerase GalE [KO:K01784] [EC:5.1.3.2]
Cspa_c19760  nucleoside-diphosphate-sugar epimerase [KO:K01784] [EC:5.1.3.2]
Cspa_c54100  NAD-dependent epimerase/dehydratase [KO:K01784] [EC:5.1.3.2]
Cspa_c12030  UDP-glucose 6-dehydrogenase [KO:K00012] [EC:1.1.1.22]
Cspa_c54310  rmlA4; glucose-1-phosphate thymidylyltransferase RmlA [KO:K00973] [EC:2.7.7.24]
Cspa_c12100  rmlA1; glucose-1-phosphate thymidylyltransferase RmlA [KO:K00973] [EC:2.7.7.24]
Cspa_c19900  rmlA2; glucose-1-phosphate thymidylyltransferase RmlA [KO:K00973] [EC:2.7.7.24]
Cspa_c25830  rmlA3; glucose-1-phosphate thymidylyltransferase RmlA [KO:K00973] [EC:2.7.7.24]
Cspa_c54290  rffG2; dTDP-glucose 4,6-dehydratase 2 [KO:K01710] [EC:4.2.1.46]
Cspa_c12130  rfbB1; dTDP-glucose 4,6-dehydratase RfbB [KO:K01710] [EC:4.2.1.46]
Cspa_c12330  rfbB2; dTDP-glucose 4,6-dehydratase RfbB [KO:K01710] [EC:4.2.1.46]
Cspa_c54300  rfbC; dTDP-4-dehydrorhamnose 3,5-epimerase RfbC [KO:K01790] [EC:5.1.3.13]
Cspa_c12110  rmlC1; dTDP-4-dehydrorhamnose 3,5-epimerase RmlC [KO:K01790] [EC:5.1.3.13]
Cspa_c12310  rmlC2; dTDP-4-dehydrorhamnose 3,5-epimerase RmlC [KO:K01790] [EC:5.1.3.13]
Cspa_c28910  dTDP-4-dehydrorhamnose reductase [KO:K00067] [EC:1.1.1.133]
Cspa_c54270  dTDP-4-dehydrorhamnose reductase [KO:K00067] [EC:1.1.1.133]
Cspa_c12120  spsK1; spore coat polysaccharide biosynthesis protein SpsK [KO:K00067] [EC:1.1.1.133]
Cspa_c12320  spsK2; spore coat polysaccharide biosynthesis protein SpsK [KO:K00067] [EC:1.1.1.133]
Cspa_c54150  rfbF; glucose-1-phosphate cytidylyltransferase RfbF [KO:K00978] [EC:2.7.7.33]
Cspa_c54140  rfbG; CDP-glucose 4,6-dehydratase RfbG [KO:K01709] [EC:4.2.1.45]
Cspa_c54130  rfbH; lipopolysaccharide biosynthesis protein RfbH [KO:K12452] [EC:1.17.1.1]
Cspa_c52710  pmi; mannose-6-phosphate isomerase Pmi [KO:K01809] [EC:5.3.1.8]
Cspa_c10820  gmuF; putative mannose-6-phosphate isomerase GmuF [KO:K01809] [EC:5.3.1.8]
Cspa_c45460  mannose-6-phosphate isomerase [KO:K01809] [EC:5.3.1.8]
Cspa_c04300  manC; mannose-1-phosphate guanylyltransferase ManC [KO:K00971] [EC:2.7.7.13]
Cspa_c03670  rfbA; putative mannose-1-phosphate guanylyltransferase RfbA [KO:K00971] [EC:2.7.7.13]
Cspa_c01040  glmU; bifunctional protein GlmU [KO:K04042] [EC:2.7.7.23 2.3.1.157]
Cspa_c06170  wecB; UDP-N-acetylglucosamine 2-epimerase WecB [KO:K01791] [EC:5.1.3.14]
Cspa_c45680  pseB; UDP-N-acetylglucosamine 4,6-dehydratase PseD [KO:K15894] [EC:4.2.1.115 5.1.3.-]
Cspa_c45300  pseG; pseudaminic acid biosynthesis-associated protein PseG [KO:K15897] [EC:3.6.1.57]
Cspa_c45320  pseI; pseudaminic acid synthase PseI [KO:K15898] [EC:2.5.1.97]
Cspa_c55370  wbpA2; UDP-N-acetyl-D-glucosamine 6-dehydrogenase WbpA [KO:K13015] [EC:1.1.1.136]
Cspa_c19780  wbpA1; UDP-N-acetyl-D-glucosamine 6-dehydrogenase WbpA [KO:K13015] [EC:1.1.1.136]
Cspa_c53470  putative dehydrogenase [KO:K13020] [EC:1.1.1.335]
Cspa_c55380  wbpD; UDP-2-acetamido-3-amino-2,3-dideoxy-D-glucuronate N-acetyltransferase WbpD [KO:K13018] [EC:2.3.1.201]
Cspa_c53520  UDP-N-acetylglucosamine 2-epimerase [KO:K13019] [EC:5.1.3.23]
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
  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
csr00520  Amino sugar and nucleotide sugar metabolism
KO pathway
ko00541   
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