KEGG   PATHWAY: bcel00541
Entry
bcel00541                   Pathway                                
Name
O-Antigen nucleotide sugar biosynthesis - Bacteroides cellulosilyticus
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
bcel00541  O-Antigen nucleotide sugar biosynthesis
bcel00541

Module
bcel_M00793  dTDP-L-rhamnose biosynthesis [PATH:bcel00541]
Organism
Bacteroides cellulosilyticus [GN:bcel]
Gene
BcellWH2_00556  lnpD; UDP-glucose 4-epimerase [KO:K01784] [EC:5.1.3.2]
BcellWH2_00493  glf_1; UDP-galactopyranose mutase [KO:K01854] [EC:5.4.99.9]
BcellWH2_03834  glf_2; UDP-galactopyranose mutase [KO:K01854] [EC:5.4.99.9]
BcellWH2_04364  ugd; UDP-glucose 6-dehydrogenase [KO:K00012] [EC:1.1.1.22]
BcellWH2_05426  tuaD; UDP-glucose 6-dehydrogenase TuaD [KO:K00012] [EC:1.1.1.22]
BcellWH2_01451  rmlA2; Glucose-1-phosphate thymidylyltransferase 2 [KO:K00973] [EC:2.7.7.24]
BcellWH2_01450  rffG; dTDP-glucose 4,6-dehydratase 2 [KO:K01710] [EC:4.2.1.46]
BcellWH2_01427  rfbC_1; dTDP-4-dehydrorhamnose 3,5-epimerase [KO:K01790] [EC:5.1.3.13]
BcellWH2_05427  rfbC_5; dTDP-4-dehydrorhamnose 3,5-epimerase [KO:K01790] [EC:5.1.3.13]
BcellWH2_01776  rfbC_2; dTDP-4-dehydrorhamnose 3,5-epimerase [KO:K01790] [EC:5.1.3.13]
BcellWH2_03960  rfbC_3; dTDP-4-dehydrorhamnose 3,5-epimerase [KO:K01790] [EC:5.1.3.13]
BcellWH2_04973  rfbC_4; dTDP-4-dehydrorhamnose 3,5-epimerase [KO:K01790] [EC:5.1.3.13]
BcellWH2_00077  rmlD_1; dTDP-4-dehydrorhamnose reductase [KO:K00067] [EC:1.1.1.133]
BcellWH2_01311  rmlD_2; dTDP-4-dehydrorhamnose reductase [KO:K00067] [EC:1.1.1.133]
BcellWH2_00916  gmuF; putative mannose-6-phosphate isomerase GmuF [KO:K01809] [EC:5.3.1.8]
BcellWH2_01693  algC; Phosphomannomutase/phosphoglucomutase [KO:K01840] [EC:5.4.2.8]
BcellWH2_00185  rfbM_1; Mannose-1-phosphate guanylyltransferase RfbM [KO:K00971] [EC:2.7.7.13]
BcellWH2_03304  rfbM_2; Mannose-1-phosphate guanylyltransferase RfbM [KO:K00971] [EC:2.7.7.13]
BcellWH2_00675  gmd_1; GDP-mannose 4,6-dehydratase [KO:K01711] [EC:4.2.1.47]
BcellWH2_00974  gmd_2; GDP-mannose 4,6-dehydratase [KO:K01711] [EC:4.2.1.47]
BcellWH2_00676  fcl; GDP-L-fucose synthase [KO:K02377] [EC:1.1.1.271]
BcellWH2_00699  wecB_2; UDP-N-acetylglucosamine 2-epimerase [KO:K01791] [EC:5.1.3.14]
BcellWH2_00389  wecB_1; UDP-N-acetylglucosamine 2-epimerase [KO:K01791] [EC:5.1.3.14]
BcellWH2_00628  wbpI_1; UDP-2,3-diacetamido-2,3-dideoxy-D-glucuronate 2-epimerase [KO:K01791] [EC:5.1.3.14]
BcellWH2_00700  wbpA_3; UDP-N-acetyl-D-glucosamine 6-dehydrogenase [KO:K02472] [EC:1.1.1.336]
BcellWH2_04977  capD; UDP-glucose 4-epimerase [KO:K15894] [EC:4.2.1.115 5.1.3.-]
BcellWH2_04978  NAD dependent epimerase/dehydratase family protein [KO:K19068] [EC:1.1.1.367]
BcellWH2_04979  wbpI_2; UDP-2,3-diacetamido-2,3-dideoxy-D-glucuronate 2-epimerase [KO:K24258] [EC:5.1.3.28]
BcellWH2_00199  wbpA_1; UDP-N-acetyl-D-glucosamine 6-dehydrogenase [KO:K02474] [EC:1.1.1.136 1.1.1.-]
BcellWH2_00489  wbpA_2; UDP-N-acetyl-D-glucosamine 6-dehydrogenase [KO:K02474] [EC:1.1.1.136 1.1.1.-]
BcellWH2_00978  wbpA_4; UDP-N-acetyl-D-glucosamine 6-dehydrogenase [KO:K02474] [EC:1.1.1.136 1.1.1.-]
BcellWH2_04368  fdtC; dTDP-3-amino-3,6-dideoxy-alpha-D-galactopyranose 3-N-acetyltransferase [KO:K13018] [EC:2.3.1.201]
BcellWH2_00200  UDP-glucose 4-epimerase [KO:K02473] [EC:5.1.3.7 5.1.3.-]
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
bcel00520  Amino sugar and nucleotide sugar metabolism
KO pathway
ko00541   
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