KEGG   ORTHOLOGY: K16593
Entry
K16593                      KO                                     
Symbol
bioI, CYP107H
Name
pimeloyl-[acyl-carrier protein] synthase [EC:1.14.14.46]
Pathway
map00780  Biotin metabolism
map01100  Metabolic pathways
map01240  Biosynthesis of cofactors
Module
M00573  Biotin biosynthesis, BioI pathway, long-chain-acyl-ACP => pimeloyl-ACP => biotin
Reaction
R10123  acyl-[acyl-carrier protein],reduced-flavodoxin:oxygen oxidoreductase (pimeloyl-[acyl-carrier protein] forming)
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
COG: COG2124
Genes
DRP: PSQ90_06605
AMOB: HG15A2_21140(bioI)
DFQ: NFI81_21555
DCN: MUK70_25755
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
BSO: BSNT_09439(bioI)
BSN: BSn5_05935
BSQ: B657_30190(bioI)
BSX: C663_2864(bioI)
BSP: U712_14985
BSS: BSUW23_14625(bioI)
BST: GYO_3267(bioI)
BIT: BIS30_04465
BLI: BL00957(bioI)
BLD: BLi00771(bioI)
BLH: BaLi_c08690(bioI)
BAY: RBAM_018240
BAQ: BACAU_1782(bioI)
BYA: BANAU_1949(bioI)
BQY: MUS_2177(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)
BAMI: KSO_010245
BAMC: U471_18790
BAMF: U722_09650
BSIA: CWD84_11875
BAE: BATR1942_12885
BVM: B9C48_09310
BSON: S101395_00966(bioI)
BHT: DIC78_16505
BMOJ: HC660_28830(bioI)
BIQ: AN935_15110
BSTR: QI003_18295(bioI)
BGY: BGLY_0785
BCAB: EFK13_15340
BRY: M0696_15050
BACP: SB24_00535
BACB: OY17_12255
BACY: QF06_13285
BACL: BS34A_32830(bioI)
BALM: BsLM_3003
BACS: AUL54_01465
BACQ: DOE78_13810
BAQU: K6959_16195
BAFC: K3G25_17170
BKN: WDJ61_01645
BEO: BEH_11250
BKW: BkAM31D_02760(bioI)
BGI: BGM20_09045
BPF: BpOF4_16075(bioI)
PASA: BAOM_2460(bioI)
MSEM: GMB29_12010
ROSS: V2W31_17270
ALKL: MM271_06880
DOM: RRU94_17210
ASOC: CB4_02728(bioI)
AUD: PO771_10345
FFE: LSG31_10755
KBR: Q4V65_05370
 » 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 (1)   
   COG (1)   
Gene (6)   
   OC (6)   
All databases (7)   

Download RDF
KEGG   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
DRP: PSQ90_06605
AMOB: HG15A2_21140(bioI)
DFQ: NFI81_21555
DCN: MUK70_25755
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
BSO: BSNT_09439(bioI)
BSN: BSn5_05935
BSQ: B657_30190(bioI)
BSX: C663_2864(bioI)
BSP: U712_14985
BSS: BSUW23_14625(bioI)
BST: GYO_3267(bioI)
BIT: BIS30_04465
BLI: BL00957(bioI)
BLD: BLi00771(bioI)
BLH: BaLi_c08690(bioI)
BAY: RBAM_018240
BAQ: BACAU_1782(bioI)
BYA: BANAU_1949(bioI)
BQY: MUS_2177(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)
BAMI: KSO_010245
BAMC: U471_18790
BAMF: U722_09650
BSIA: CWD84_11875
BAE: BATR1942_12885
BVM: B9C48_09310
BSON: S101395_00966(bioI)
BHT: DIC78_16505
BMOJ: HC660_28830(bioI)
BIQ: AN935_15110
BSTR: QI003_18295(bioI)
BGY: BGLY_0785
BCAB: EFK13_15340
BRY: M0696_15050
BACP: SB24_00535
BACB: OY17_12255
BACY: QF06_13285
BACL: BS34A_32830(bioI)
BALM: BsLM_3003
BACS: AUL54_01465
BACQ: DOE78_13810
BAQU: K6959_16195
BAFC: K3G25_17170
BKN: WDJ61_01645
BEO: BEH_11250
BKW: BkAM31D_02760(bioI)
BGI: BGM20_09045
BPF: BpOF4_16075(bioI)
PASA: BAOM_2460(bioI)
MSEM: GMB29_12010
ROSS: V2W31_17270
ALKL: MM271_06880
DOM: RRU94_17210
ASOC: CB4_02728(bioI)
AUD: PO771_10345
FFE: LSG31_10755
KBR: Q4V65_05370
 » 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

  All links  
Protein sequence (176)   
   UniProt (174)   
   SWISS-PROT (1)   
   RefSeq(pep) (1)   
DNA sequence (217)   
   RefSeq(nuc) (1)   
   GenBank (107)   
   EMBL (109)   
Protein domain (4)   
   InterPro (4)   
All databases (397)   

Download RDF
KEGG   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
rn01240  Biosynthesis of cofactors
Module
M00573  Biotin biosynthesis, BioI pathway, long-chain-acyl-ACP => pimeloyl-ACP => biotin
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  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
     R10123  Long-chain acyl-[acyl-carrier protein] + 2 Reduced flavodoxin + 3 Oxygen <=> Pimeloyl-[acyl-carrier protein] + n-Alkanal + 2 Oxidized flavodoxin + 3 H2O
Orthology
K16593  pimeloyl-[acyl-carrier protein] synthase [EC:1.14.14.46]
Other DBs
RHEA: 52855 52975

  All links  
No link information was found.
DBGET integrated database retrieval system