KEGG ORTHOLOGY: K16593

ORTHOLOGY: K16593

Entry

K16593 KO

Name

bioI, CYP107H

Definition

pimeloyl-[acyl-carrier protein] synthase [EC:1.14.14.46]

Pathway

ko00780

Biotin metabolism

ko01100

Metabolic pathways

Module

M00573

Biotin biosynthesis, BioI pathway, long-chain-acyl-ACP => pimeloyl-ACP => biotin

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09108 Metabolism of cofactors and vitamins
   00780 Biotin metabolism
    K16593  bioI, CYP107H; pimeloyl-[acyl-carrier protein] synthase
09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K16593  bioI, CYP107H; pimeloyl-[acyl-carrier protein] synthase
Enzymes [BR:ko01000]
1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.46  pimeloyl-[acyl-carrier protein] synthase
     K16593  bioI, CYP107H; pimeloyl-[acyl-carrier protein] synthase
Cytochrome P450 [BR:ko00199]
Cytochrome P450, bacteria type
  CYP107 family
   K16593  bioI, CYP107H; pimeloyl-[acyl-carrier protein] synthase

Other DBs

RN:

R10123

COG:

COG2124

Genes

GSN:	YC6258_03069

BSU:	BSU30190(bioI)

BSR:	I33_3073(bioI)

BSL:

A7A1_1657

BSH:	BSU6051_30190(bioI)

BSY:	I653_14450

BSUT:

BSUB_03208(bioI)

BSUL:

BSUA_03208(bioI)

BSUS:

Q433_16375

BSS:	BSUW23_14625(bioI)

BST:	GYO_3267(bioI)

BSO:	BSNT_09439(bioI)

BSN:	BSn5_05935

BSQ:	B657_30190(bioI)

BSX:	C663_2864(bioI)

BSP:	U712_14985

BLI:	BL00957(bioI)

BLD:	BLi00771(bioI)

BLH:	BaLi_c08690(bioI)

BAY:	RBAM_018240

BAQ:	BACAU_1782(bioI)

BYA:	BANAU_1949(bioI)

BAMP:

B938_09435

BAML:

BAM5036_1761(bioI)

BAMA:

RBAU_1799(bioI)

BAMN:

BASU_1779(bioI)

BAMB:

BAPNAU_1920(bioI)

BAMT:

AJ82_10365

BAMY:

V529_17940(bioI)

BMP:	NG74_01900(bioI)

BAO:	BAMF_1919(bioI)

BAZ:	BAMTA208_07910(bioI)

BQL:	LL3_02009(bioI)

BXH:	BAXH7_01611(bioI)

BQY:	MUS_2177(bioI)

BAMI:

KSO_010245

BAMC:

U471_18790

BAMF:

U722_09650

BAE:	BATR1942_12885

BVM:	B9C48_09310

BPF:	BpOF4_16075(bioI)

BACP:

SB24_00535

BACB:

OY17_12255

BACY:

QF06_13285

BACL:

BS34A_32830(bioI)

BALM:

BsLM_3003

BEO:

BEH_11250

BGY:

BGLY_0785

BGI:	BGM20_09045

BKW:	BkAM31D_02760(bioI)

BACS:

AUL54_01465

BIT:	BIS30_04465

BACQ:

DOE78_13810

ASOC:

CB4_02728(bioI)

PVS:	A1sIA79_01425

ABAS:

ACPOL_1393

PCM:	AY601_4428

LACI:

CW733_04675

» show all

Reference

PMID:8763940

Authors

Bower S, Perkins JB, Yocum RR, Howitt CL, Rahaim P, Pero J

Title

Cloning, sequencing, and characterization of the Bacillus subtilis biotin biosynthetic operon.

Journal

J Bacteriol 178:4122-30 (1996)
DOI:10.1128/JB.178.14.4122-4130.1996

Sequence

[bsu:BSU30190]

Reference

PMID:11368323

Authors

Stok JE, De Voss J

Title

Expression, purification, and characterization of BioI: a carbon-carbon bond cleaving cytochrome P450 involved in biotin biosynthesis in Bacillus subtilis.

Journal

Arch Biochem Biophys 384:351-60 (2000)
DOI:10.1006/abbi.2000.2067

Reference

PMID:21437340

Authors

Lin S, Cronan JE

Title

Closing in on complete pathways of biotin biosynthesis.

Journal

Mol Biosyst 7:1811-21 (2011)
DOI:10.1039/c1mb05022b

All links

Ontology (4)   
   KEGG BRITE (3)   
   COG (1)   
Pathway (5)   
   KEGG PATHWAY (4)   
   KEGG MODULE (1)   
Chemical reaction (2)   
   KEGG ENZYME (1)   
   KEGG REACTION (1)   
Gene (64)   
   KEGG GENES (58)   
   OC (6)   
Protein sequence (25)   
   UniProt (24)   
   SWISS-PROT (1)   
Literature (3)   
   PubMed (3)   
All databases (103)   

Download RDF

ENZYME: 1.14.14.46

Entry

EC 1.14.14.46 Enzyme

Name

pimeloyl-[acyl-carrier protein] synthase;
bioI (gene name);
P450BioI;
CYP107H1

Class

Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor

Sysname

acyl-[acyl-carrier protein],reduced-flavodoxin:oxygen oxidoreductase (pimeloyl-[acyl-carrier protein] forming)

Reaction(IUBMB)

a long-chain acyl-[acyl-carrier protein] + 2 reduced flavodoxin + 3 O2 = pimeloyl-[acyl-carrier protein] + an n-alkanal + 2 oxidized flavodoxin + 3 H2O (overall reaction) [RN:R10123];
(1a) a long-chain acyl-[acyl-carrier protein] + reduced flavodoxin + O2 = a (7S)-7-hydroxy-long-chain-acyl-[acyl-carrier protein] + oxidized flavodoxin + H2O;
(1b) a (7S)-7-hydroxy-long-chain-acyl-[acyl-carrier protein] + reduced flavodoxin + O2 = a (7R,8R)-7,8-dihydroxy-long-chain-acyl-[acyl-carrier protein] + oxidized flavodoxin + H2O;
(1c) a (7R,8R)-7,8-dihydroxy-long-chain-acyl-[acyl-carrier protein] + reduced flavodoxin + O2 = a 7-oxoheptanoyl-[acyl-carrier protein] + an n-alkanal + oxidized flavodoxin + 2 H2O;
(1d) a 7-oxoheptanoyl-[acyl-carrier protein] + oxidized flavodoxin + H2O = a pimeloyl-[acyl-carrier protein] + reduced flavodoxin + H+

Reaction(KEGG)

R10123

Substrate

long-chain acyl-[acyl-carrier protein] [CPD:C20683];
reduced flavodoxin [CPD:C02745];
O2 [CPD:C00007];
(7S)-7-hydroxy-long-chain-acyl-[acyl-carrier protein];
(7R,8R)-7,8-dihydroxy-long-chain-acyl-[acyl-carrier protein];
7-oxoheptanoyl-[acyl-carrier protein];
oxidized flavodoxin [CPD:C02869];
H2O [CPD:C00001]

Product

pimeloyl-[acyl-carrier protein] [CPD:C19845];
n-alkanal [CPD:C15596];
oxidized flavodoxin [CPD:C02869];
H2O [CPD:C00001];
(7S)-7-hydroxy-long-chain-acyl-[acyl-carrier protein];
(7R,8R)-7,8-dihydroxy-long-chain-acyl-[acyl-carrier protein];
7-oxoheptanoyl-[acyl-carrier protein];
reduced flavodoxin [CPD:C02745];
H+ [CPD:C00080]

Comment

A cytochrome P-450 (heme-thiolate) protein. The enzyme catalyses an oxidative C-C bond cleavage of long-chain acyl-[acyl-carrier protein]s of various lengths to generate pimeloyl-[acyl-carrier protein], an intermediate in the biosynthesis of biotin. The preferred substrate of the enzyme from the bacterium Bacillus subtilis is palmitoyl-[acyl-carrier protein] which then gives heptanal as the alkanal. The mechanism is similar to EC 1.14.15.6, cholesterol monooxygenase (side-chain-cleaving), followed by a hydroxylation step, which may occur spontaneously [2].

History

EC 1.14.14.46 created 2013 as EC 1.14.15.12, transferred 2017 to EC 1.14.14.46

Pathway

ec00780

Biotin metabolism

Orthology

K16593

pimeloyl-[acyl-carrier protein] synthase

Genes

GSN:	YC6258_03069

BSU:	BSU30190(bioI)

BSR:	I33_3073(bioI)

BSL:

A7A1_1657

BSH:	BSU6051_30190(bioI)

BSY:	I653_14450

BSUT:

BSUB_03208(bioI)

BSUL:

BSUA_03208(bioI)

BSUS:

Q433_16375

BSS:	BSUW23_14625(bioI)

BST:	GYO_3267(bioI)

BSO:	BSNT_09439(bioI)

BSN:	BSn5_05935

BSQ:	B657_30190(bioI)

BSX:	C663_2864(bioI)

BSP:	U712_14985

BLI:	BL00957(bioI)

BLD:	BLi00771(bioI)

BLH:	BaLi_c08690(bioI)

BAY:	RBAM_018240

BAQ:	BACAU_1782(bioI)

BYA:	BANAU_1949(bioI)

BAMP:

B938_09435

BAML:

BAM5036_1761(bioI)

BAMA:

RBAU_1799(bioI)

BAMN:

BASU_1779(bioI)

BAMB:

BAPNAU_1920(bioI)

BAMT:

AJ82_10365

BAMY:

V529_17940(bioI)

BMP:	NG74_01900(bioI)

BAO:	BAMF_1919(bioI)

BAZ:	BAMTA208_07910(bioI)

BQL:	LL3_02009(bioI)

BXH:	BAXH7_01611(bioI)

BQY:	MUS_2177(bioI)

BAMI:

KSO_010245

BAMC:

U471_18790

BAMF:

U722_09650

BAE:	BATR1942_12885

BVM:	B9C48_09310

BPF:	BpOF4_16075(bioI)

BACP:

SB24_00535

BACB:

OY17_12255

BACY:

QF06_13285

BACL:

BS34A_32830(bioI)

BALM:

BsLM_3003

BEO:

BEH_11250

BGY:

BGLY_0785

BGI:	BGM20_09045

BKW:	BkAM31D_02760(bioI)

BACS:

AUL54_01465

BIT:	BIS30_04465

BACQ:

DOE78_13810

ASOC:

CB4_02728(bioI)

PVS:	A1sIA79_01425

ABAS:

ACPOL_1393

PCM:	AY601_4428

LACI:

CW733_04675

» show all

Reference

1 [PMID:11368323]

Authors

Stok JE, De Voss J.

Title

Expression, purification, and characterization of BioI: a carbon-carbon bond cleaving cytochrome P450 involved in biotin biosynthesis in Bacillus subtilis.

Journal

Arch Biochem Biophys 384:351-60 (2000)
DOI:10.1006/abbi.2000.2067

Reference

2 [PMID:14737344]

Authors

Cryle MJ, De Voss JJ

Title

Carbon-carbon bond cleavage by cytochrome p450(BioI)(CYP107H1).

Journal

Chem Commun (Camb) 86-7 (2004)
DOI:10.1039/b311652b

Reference

3 [PMID:18838690]

Authors

Cryle MJ, Schlichting I.

Title

Structural insights from a P450 Carrier Protein complex reveal how specificity is achieved in the P450(BioI) ACP complex.

Journal

Proc Natl Acad Sci U S A 105:15696-701 (2008)
DOI:10.1073/pnas.0805983105

Sequence

[bsu:BSU30190]

Reference

4 [PMID:20658980]

Authors

Cryle MJ

Title

Selectivity in a barren landscape: the P450(BioI)-ACP complex.

Journal

Biochem Soc Trans 38:934-9 (2010)
DOI:10.1042/BST0380934

Other DBs

ExplorEnz - The Enzyme Database:

1.14.14.46

IUBMB Enzyme Nomenclature:

1.14.14.46

ExPASy - ENZYME nomenclature database:

1.14.14.46

BRENDA, the Enzyme Database:

1.14.14.46

REACTION: R10123

Entry

R10123 Reaction

Name

acyl-[acyl-carrier protein],reduced-flavodoxin:oxygen oxidoreductase (pimeloyl-[acyl-carrier protein] forming)

Definition

Long-chain acyl-[acyl-carrier protein] + 2 Reduced flavodoxin + 3 Oxygen <=> Pimeloyl-[acyl-carrier protein] + n-Alkanal + 2 Oxidized flavodoxin + 3 H2O

Equation

C20683 + 2 C02745 + 3 C00007 <=> C19845 + C15596 + 2 C02869 + 3 C00001

Enzyme

1.14.14.46

Pathway

rn00780

Biotin metabolism

rn01100

Metabolic pathways

Module

M00573

Biotin biosynthesis, BioI pathway, long-chain-acyl-ACP => pimeloyl-ACP => biotin

Orthology

K16593

pimeloyl-[acyl-carrier protein] synthase [EC:1.14.14.46]

Other DBs

RHEA:

52975

All links

Ontology (1)   
   KEGG BRITE (1)   
Pathway (5)   
   KEGG PATHWAY (4)   
   KEGG MODULE (1)   
Chemical substance (7)   
   KEGG COMPOUND (7)   
Chemical reaction (1)   
   KEGG ENZYME (1)   
Gene (59)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (58)   
All databases (73)   

Download RDF

DBGET integrated database retrieval system