KEGG   ORTHOLOGY: K16593Help
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
BRITE hierarchy
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)
BSQ: B657_30190(bioI)
BSX: C663_2864(bioI)
BLI: BL00957(bioI)
BLD: BLi00771(bioI)
BLH: BaLi_c08690(bioI)
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
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
BKW: BkAM31D_02760(bioI)
ASOC: CB4_02728(bioI)
ABAS: ACPOL_1393
 » show all
TaxonomyKoalaUniProt
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
  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
  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

KEGG   ENZYME: 1.14.14.46Help
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
BRITE hierarchy
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)
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)
BSQ: B657_30190(bioI)
BSX: C663_2864(bioI)
BLI: BL00957(bioI)
BLD: BLi00771(bioI)
BLH: BaLi_c08690(bioI)
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
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
BKW: BkAM31D_02760(bioI)
ASOC: CB4_02728(bioI)
ABAS: ACPOL_1393
 » show all
Taxonomy
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

KEGG   REACTION: R10123Help
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
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

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