KEGG ENZYME: 4.1.99.23

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

GSU:	GSU3005(thiC-2)

GSK:	KN400_2948(thiC-2)

GME:	Gmet_0471(thiC-2)

GPI:	GPICK_02630

GAO:	A2G06_14140

GBZ:	JZM60_08015(thiC)

GEM:

GM21_3893

GEB:

GM18_4239

GEF:	FO488_14370(thiC)

GUR:

Gura_4183

GEO:	Geob_0543(thiC-2)

GLO:

Glov_3677

TAMM:

GEAMG1_2108(bzaF)

GBM:	Gbem_3809(thiC-2)

GBN:	GEOBRER4_37000(thiC)

GER:	KP004_18205(thiC)

GSUB:

KP001_18030(thiC)

GNT:	KP003_18225(thiC)

GPL:	M1B72_01565(thiC)

GHC:	L9S41_11450(thiC)

PPD:

Ppro_2809

DEU:

DBW_3101

DVE:	DESUT3_08050(thiC)

DEP:	AOP6_0798(thiC)

DES:	DSOUD_0618(thiC-2)

DSF:

UWK_02784

DAK:	DaAHT2_1596

DBK:	DGMP_09610(thiC_1)

DDU:	GF1_11200(thiC)

ECOM:

QTN59_15175(thiC)

DAL:

Dalk_0439

DAT:	HRM2_06760(thiC)

DTO:	TOL2_C39750(thiC2)

DWD:	DSCW_64740(thiC)

DALK:

DSCA_61910(thiC_2)

DML:	Dmul_38190(thiC2)

DLI:	dnl_04700(thiC2)

DEK:	DSLASN_49290(thiC_2)

DBR:

Deba_2032

DMP:	FAK_24670(thiC)

TAV:	G4V39_09730(thiC)

TMAI:

FVE67_00935(thiC)

DHR:	LGS26_04000(thiC)

CACE:

CACET_c19200(thiC1) CACET_c19210(thiC2)

CFM:	BJL90_15685 BJL90_15690

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

DGI:	Desgi_1093 Desgi_1094

ELM:	ELI_4215 ELI_4216

EMT:	CPZ25_011275 CPZ25_011280

ELIM:

B2M23_05585 B2M23_05590

AWO:	Awo_c14630(thiC2) Awo_c14640(thiC3)

AWI:	CHL1_002404(thiC) CHL1_002405(bzaB)

TPZ:	Tph_c22270(thiC2) Tph_c22280(thiC3)

MTA:	Moth_1722 Moth_1723

MTHO:

MOTHE_c17310(thiC2) MOTHE_c17320(thiC3)

MTHZ:

MOTHA_c18140(thiC2) MOTHA_c18150(thiC3)

CALK:

HUE98_02155(thiC) HUE98_02160(bzaB)

DFO:	Dform_00448(thiC) Dform_00449

BROC:

IPI25_07410(thiC)

BPIT:

BPIT_18350

DTP:	JZK55_23310(thiC_2)

» 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

[elm:ELI_4215 ELI_4216] [mta:Moth_1723 Moth_1722]

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

DBGET integrated database retrieval system