KEGG   ORTHOLOGY: K22465
Entry
K22465                      KO                                     
Symbol
bzaA_B
Name
5-hydroxybenzimidazole synthase [EC:4.1.99.23]
Pathway
map00860  Porphyrin metabolism
map01100  Metabolic pathways
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09108 Metabolism of cofactors and vitamins
   00860 Porphyrin metabolism
    K22465  bzaA_B; 5-hydroxybenzimidazole synthase
Enzymes [BR:ko01000]
 4. Lyases
  4.1  Carbon-carbon lyases
   4.1.99  Other carbon-carbon lyases
    4.1.99.23  5-hydroxybenzimidazole synthase
     K22465  bzaA_B; 5-hydroxybenzimidazole synthase
Other DBs
RN: R11919
Genes
CACE: CACET_c19200(thiC1) CACET_c19210(thiC2)
CFM: BJL90_15685 BJL90_15690
CALK: HUE98_02155(thiC) HUE98_02160(bzaB)
DOR: Desor_2648 Desor_2649
DAI: Desaci_2510 Desaci_2511
DMI: Desmer_3480 Desmer_3481
DAE: Dtox_1596 Dtox_1597
DKU: Desku_0278 Desku_0279
AACX: DEACI_0774 DEACI_0775
TJR: TherJR_0550 TherJR_0551
AWO: Awo_c14630(thiC2) Awo_c14640(thiC3)
MTHO: MOTHE_c17310(thiC2) MOTHE_c17320(thiC3)
MTHZ: MOTHA_c18140(thiC2) MOTHA_c18150(thiC3)
TPZ: Tph_c22270(thiC2) Tph_c22280(thiC3)
 » show all
Reference
  Authors
Hazra AB, Han AW, Mehta AP, Mok KC, Osadchiy V, Begley TP, Taga ME
  Title
Anaerobic biosynthesis of the lower ligand of vitamin B12.
  Journal
Proc Natl Acad Sci U S A 112:10792-7 (2015)
DOI:10.1073/pnas.1509132112
  Sequence
LinkDB

KEGG   ORTHOLOGY: K22466
Entry
K22466                      KO                                     
Symbol
bzaF
Name
5-hydroxybenzimidazole synthase [EC:4.1.99.23]
Pathway
map00860  Porphyrin metabolism
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09108 Metabolism of cofactors and vitamins
   00860 Porphyrin metabolism
    K22466  bzaF; 5-hydroxybenzimidazole synthase
Enzymes [BR:ko01000]
 4. Lyases
  4.1  Carbon-carbon lyases
   4.1.99  Other carbon-carbon lyases
    4.1.99.23  5-hydroxybenzimidazole synthase
     K22466  bzaF; 5-hydroxybenzimidazole synthase
Other DBs
RN: R11919
Genes
GSU: GSU3005(thiC-2)
GSK: KN400_2948(thiC-2)
GME: Gmet_0471(thiC-2)
GEM: GM21_3893
GEB: GM18_4239
GPI: GPICK_02630
GAO: A2G06_14140
GEF: FO488_14370(thiC)
GBZ: JZM60_08015(thiC)
GUR: Gura_4183
GEO: Geob_0543(thiC-2)
GLO: Glov_3677
GBM: Gbem_3809(thiC-2)
GBN: GEOBRER4_37000(thiC)
GER: KP004_18205(thiC)
GSUB: KP001_18030(thiC)
GNT: KP003_18225(thiC)
PPD: Ppro_2809
DES: DSOUD_0618(thiC-2)
DEU: DBW_3101
DVE: DESUT3_08050(thiC)
DSF: UWK_02784
DBK: DGMP_09610(thiC_1)
DML: Dmul_38190(thiC2)
DAL: Dalk_0439
DAT: HRM2_06760(thiC)
DTO: TOL2_C39750(thiC2)
DWD: DSCW_64740(thiC)
DALK: DSCA_61910(thiC_2)
DLI: dnl_04700(thiC2)
DEK: DSLASN_49290(thiC_2)
DBR: Deba_2032
DHR: LGS26_04000(thiC)
BROC: IPI25_07410(thiC)
BPIT: BPIT_18350
DTP: JZK55_23310(thiC_2)
TAV: G4V39_09730(thiC)
TMAI: FVE67_00935(thiC)
 » show all
Reference
  Authors
Mehta AP, Abdelwahed SH, Fenwick MK, Hazra AB, Taga ME, Zhang Y, Ealick SE, Begley TP
  Title
Anaerobic 5-Hydroxybenzimidazole Formation from Aminoimidazole Ribotide: An Unanticipated Intersection of Thiamin and Vitamin B(1)(2) Biosynthesis.
  Journal
J Am Chem Soc 137:10444-7 (2015)
DOI:10.1021/jacs.5b03576
LinkDB

KEGG   ENZYME: 4.1.99.23
Entry
EC 4.1.99.23                Enzyme                                 
Name
5-hydroxybenzimidazole synthase;
bzaF (gene name);
HBI synthase
Class
Lyases;
Carbon-carbon lyases;
Other carbon-carbon lyases
Sysname
5-amino-1-(5-phospho-beta-D-ribosyl)imidazole formate-lyase (5-hydroxybenzimidazole-forming)
Reaction(IUBMB)
5-amino-1-(5-phospho-beta-D-ribosyl)imidazole + S-adenosyl-L-methionine + reduced acceptor = 5-hydroxybenzimidazole + 5'-deoxyadenosine + L-methionine + formate + NH3 + phosphate + oxidized acceptor [RN:R11919]
Reaction(KEGG)
R11919
Substrate
5-amino-1-(5-phospho-beta-D-ribosyl)imidazole [CPD:C03373];
S-adenosyl-L-methionine [CPD:C00019];
reduced acceptor [CPD:C00030]
Product
5-hydroxybenzimidazole [CPD:C21764];
5'-deoxyadenosine [CPD:C05198];
L-methionine [CPD:C00073];
formate [CPD:C00058];
NH3 [CPD:C00014];
phosphate [CPD:C00009];
oxidized acceptor
Comment
The enzyme, purified from bacteria, is part of the anaerobic pathway for cobalamin biosynthesis. It binds a [4Fe-4S] cluster that is coordinated by 3 cysteines and an exchangeable S-adenosyl-L-methionine molecule. The first stage of catalysis is reduction of the S-adenosyl-L-methionine to produce L-methionine and a 5'-deoxyadenosin-5'-yl radical that is crucial for the conversion of the substrate.
History
EC 4.1.99.23 created 2017
Pathway
ec00860  Porphyrin metabolism
ec01100  Metabolic pathways
Orthology
K22465  5-hydroxybenzimidazole synthase
K22466  5-hydroxybenzimidazole synthase
Genes
GSUGSU3005(thiC-2)
GSKKN400_2948(thiC-2)
GMEGmet_0471(thiC-2)
GEMGM21_3893
GEBGM18_4239
GPIGPICK_02630
GAOA2G06_14140
GEFFO488_14370(thiC)
GBZJZM60_08015(thiC)
GURGura_4183
GEOGeob_0543(thiC-2)
GLOGlov_3677
GBMGbem_3809(thiC-2)
GBNGEOBRER4_37000(thiC)
GERKP004_18205(thiC)
GSUBKP001_18030(thiC)
GNTKP003_18225(thiC)
PPDPpro_2809
DESDSOUD_0618(thiC-2)
DEUDBW_3101
DVEDESUT3_08050(thiC)
DSFUWK_02784
DAKDaAHT2_1596
DBKDGMP_09610(thiC_1)
DMLDmul_38190(thiC2)
DALDalk_0439
DATHRM2_06760(thiC)
DTOTOL2_C39750(thiC2)
DWDDSCW_64740(thiC)
DALKDSCA_61910(thiC_2)
DLIdnl_04700(thiC2)
DEKDSLASN_49290(thiC_2)
DBRDeba_2032
DHRLGS26_04000(thiC)
CACECACET_c19200(thiC1) CACET_c19210(thiC2)
CFMBJL90_15685 BJL90_15690
CALKHUE98_02155(thiC) HUE98_02160(bzaB)
DORDesor_2648 Desor_2649
DAIDesaci_2510 Desaci_2511
DMIDesmer_3480 Desmer_3481
DAEDtox_1596 Dtox_1597
DKUDesku_0278 Desku_0279
AACXDEACI_0774 DEACI_0775
TJRTherJR_0550 TherJR_0551
DGIDesgi_1093 Desgi_1094
ELMELI_4215 ELI_4216
EMTCPZ25_011275 CPZ25_011280
ELIMB2M23_05585 B2M23_05590
AWOAwo_c14630(thiC2) Awo_c14640(thiC3)
MTAMoth_1722 Moth_1723
MTHOMOTHE_c17310(thiC2) MOTHE_c17320(thiC3)
MTHZMOTHA_c18140(thiC2) MOTHA_c18150(thiC3)
TPZTph_c22270(thiC2) Tph_c22280(thiC3)
DFODform_00448(thiC) Dform_00449
BROCIPI25_07410(thiC)
BPITBPIT_18350
DTPJZK55_23310(thiC_2)
TAVG4V39_09730(thiC)
TMAIFVE67_00935(thiC)
 » show all
Reference
1  [PMID:26237670]
  Authors
Mehta AP, Abdelwahed SH, Fenwick MK, Hazra AB, Taga ME, Zhang Y, Ealick SE, Begley TP
  Title
Anaerobic 5-Hydroxybenzimidazole Formation from Aminoimidazole Ribotide: An Unanticipated Intersection of Thiamin and Vitamin B(1)(2) Biosynthesis.
  Journal
J Am Chem Soc 137:10444-7 (2015)
DOI:10.1021/jacs.5b03576
Reference
2  [PMID:26246619]
  Authors
Hazra AB, Han AW, Mehta AP, Mok KC, Osadchiy V, Begley TP, Taga ME
  Title
Anaerobic biosynthesis of the lower ligand of vitamin B12.
  Journal
Proc Natl Acad Sci U S A 112:10792-7 (2015)
DOI:10.1073/pnas.1509132112
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 4.1.99.23
IUBMB Enzyme Nomenclature: 4.1.99.23
ExPASy - ENZYME nomenclature database: 4.1.99.23
BRENDA, the Enzyme Database: 4.1.99.23
LinkDB

KEGG   REACTION: R11919
Entry
R11919                      Reaction                               
Name
5-amino-1-(5-phospho-beta-D-ribosyl)imidazole formate-lyase (5-hydroxybenzimidazole-forming)
Definition
Aminoimidazole ribotide + S-Adenosyl-L-methionine + Reduced acceptor <=> 5-Hydroxybenzimidazole + 5'-Deoxyadenosine + L-Methionine + Formate + Ammonia + Orthophosphate + Acceptor
Equation
Reaction class
RC03252  C00058_C03373
Enzyme
Pathway
rn00860  Porphyrin metabolism
rn01100  Metabolic pathways
Orthology
K22465  5-hydroxybenzimidazole synthase [EC:4.1.99.23]
K22466  5-hydroxybenzimidazole synthase [EC:4.1.99.23]
Other DBs
RHEA: 53507
LinkDB

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