KEGG   ORTHOLOGY: K13561Help
Entry
K13561                      KO                                     

Name
btrO
Definition
4-(gamma-L-glutamylamino)butanoyl-[BtrI acyl-carrier protein] monooxygenase [EC:1.14.14.13]
Pathway
ko00524  Neomycin, kanamycin and gentamicin biosynthesis
ko01130  Biosynthesis of antibiotics
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00524 Neomycin, kanamycin and gentamicin biosynthesis
    K13561  btrO; 4-(gamma-L-glutamylamino)butanoyl-[BtrI acyl-carrier protein] monooxygenase
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
    1.14.14.13  4-(gamma-L-glutamylamino)butanoyl-[BtrI acyl-carrier protein] monooxygenase
     K13561  btrO; 4-(gamma-L-glutamylamino)butanoyl-[BtrI acyl-carrier protein] monooxygenase
BRITE hierarchy
Other DBs
RN: R08908
Genes
AG: BAE07076(btrO)
TaxonomyKoalaUniProt
Reference
  Authors
Kudo F, Numakura M, Tamegai H, Yamamoto H, Eguchi T, Kakinuma K
  Title
Extended sequence and functional analysis of the butirosin biosynthetic gene cluster in Bacillus circulans SANK 72073.
  Journal
J Antibiot (Tokyo) 58:373-9 (2005)
DOI:10.1038/ja.2005.47
  Sequence
Reference
  Authors
Kudo F, Eguchi T
  Title
Biosynthetic enzymes for the aminoglycosides butirosin and neomycin.
  Journal
Methods Enzymol 459:493-519 (2009)
DOI:10.1016/S0076-6879(09)04620-5
Reference
  Authors
Li Y, Llewellyn NM, Giri R, Huang F, Spencer JB
  Title
Biosynthesis of the unique amino acid side chain of butirosin: possible protective-group chemistry in an acyl carrier protein-mediated pathway.
  Journal
Chem Biol 12:665-75 (2005)
DOI:10.1016/j.chembiol.2005.04.010

KEGG   ORTHOLOGY: K13562Help
Entry
K13562                      KO                                     

Name
btrV, btrU
Definition
NAD(P)H:FMN oxidoreductase [EC:1.5.1.-]
Pathway
ko00524  Neomycin, kanamycin and gentamicin biosynthesis
ko01130  Biosynthesis of antibiotics
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00524 Neomycin, kanamycin and gentamicin biosynthesis
    K13562  btrV, btrU; NAD(P)H:FMN oxidoreductase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.5  Acting on the CH-NH group of donors
   1.5.1  With NAD+ or NADP+ as acceptor
    1.5.1.-  
     K13562  btrV, btrU; NAD(P)H:FMN oxidoreductase
BRITE hierarchy
Other DBs
RN: R05705 R05706
COG: COG2249
Genes
AG: BAE07058(btrU)
TaxonomyKoalaUniProt
Reference
  Authors
Kudo F, Numakura M, Tamegai H, Yamamoto H, Eguchi T, Kakinuma K
  Title
Extended sequence and functional analysis of the butirosin biosynthetic gene cluster in Bacillus circulans SANK 72073.
  Journal
J Antibiot (Tokyo) 58:373-9 (2005)
DOI:10.1038/ja.2005.47
  Sequence
Reference
  Authors
Kudo F, Eguchi T
  Title
Biosynthetic enzymes for the aminoglycosides butirosin and neomycin.
  Journal
Methods Enzymol 459:493-519 (2009)
DOI:10.1016/S0076-6879(09)04620-5
Reference
  Authors
Li Y, Llewellyn NM, Giri R, Huang F, Spencer JB
  Title
Biosynthesis of the unique amino acid side chain of butirosin: possible protective-group chemistry in an acyl carrier protein-mediated pathway.
  Journal
Chem Biol 12:665-75 (2005)
DOI:10.1016/j.chembiol.2005.04.010

KEGG   ENZYME: 1.14.14.13Help
Entry
EC 1.14.14.13               Enzyme                                 

Name
4-(gamma-L-glutamylamino)butanoyl-[BtrI acyl-carrier protein] monooxygenase;
btrO (gene name)
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
4-(gamma-L-glutamylamino)butanoyl-[BtrI acyl-carrier protein],FMNH2:oxygen oxidoreductase (2-hydroxylating)
Reaction(IUBMB)
4-(gamma-L-glutamylamino)butanoyl-[BtrI acyl-carrier protein] + FMNH2 + O2 = 4-(gamma-L-glutamylamino)-(2S)-2-hydroxybutanoyl-[BtrI acyl-carrier protein] + FMN + H2O [RN:R08908]
Reaction(KEGG)
Substrate
4-(gamma-L-glutamylamino)butanoyl-[BtrI acyl-carrier protein];
FMNH2 [CPD:C01847];
O2 [CPD:C00007]
Product
4-(gamma-L-glutamylamino)-(2S)-2-hydroxybutanoyl-[BtrI acyl-carrier protein];
FMN [CPD:C00061];
H2O [CPD:C00001]
Comment
Catalyses a step in the biosynthesis of the side chain of the aminoglycoside antibiotics of the butirosin family. FMNH2 is used as a free cofactor. Forms a complex with a dedicated NAD(P)H:FMN oxidoreductase. The enzyme is not able to hydroxylate free substrates, activation by the acyl-carrier protein is mandatory.
Octanoyl-S-[BtrI acyl-carrier protein] is also accepted.
History
EC 1.14.14.13 created 2012
Pathway
ec00524  Neomycin, kanamycin and gentamicin biosynthesis
ec01130  Biosynthesis of antibiotics
Orthology
K13561  4-(gamma-L-glutamylamino)butanoyl-[BtrI acyl-carrier protein] monooxygenase
Reference
1  [PMID:15975512]
  Authors
Li Y, Llewellyn NM, Giri R, Huang F, Spencer JB
  Title
Biosynthesis of the unique amino acid side chain of butirosin: possible protective-group chemistry in an acyl carrier protein-mediated pathway.
  Journal
Chem Biol 12:665-75 (2005)
DOI:10.1016/j.chembiol.2005.04.010
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.13
IUBMB Enzyme Nomenclature: 1.14.14.13
ExPASy - ENZYME nomenclature database: 1.14.14.13
BRENDA, the Enzyme Database: 1.14.14.13

KEGG   REACTION: R08908Help
Entry
R08908                      Reaction                               

Name
4-(gamma-L-glutamylamino)butanoyl-[acp],reduced-FMN:oxygen oxidoreductase
Definition
4-(gamma-L-Glutamylamino)butanoyl-[acp] + Reduced FMN + Oxygen <=> 4-(gamma-L-Glutamylamino)-(2S)-2-hydroxybutanoyl-[acp] + FMN + H2O
Equation
Reaction class
RC00126  C00061_C01847
RC02402  C18008_C18009
Enzyme
Pathway
rn00524  Neomycin, kanamycin and gentamicin biosynthesis
rn01130  Biosynthesis of antibiotics
Orthology
K13561  4-(gamma-L-glutamylamino)butanoyl-[BtrI acyl-carrier protein] monooxygenase [EC:1.14.14.13]
Other DBs
RHEA: 53963

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