KEGG   ORTHOLOGY: K13549Help
Entry
K13549                      KO                                     

Name
btrN
Definition
2-deoxy-scyllo-inosamine dehydrogenase (SAM-dependent) [EC:1.1.99.38]
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
    K13549  btrN; 2-deoxy-scyllo-inosamine dehydrogenase (SAM-dependent)
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.1  Acting on the CH-OH group of donors
   1.1.99  With unknown physiological acceptors
    1.1.99.38  2-deoxy-scyllo-inosamine dehydrogenase (AdoMet-dependent)
     K13549  btrN; 2-deoxy-scyllo-inosamine dehydrogenase (SAM-dependent)
BRITE hierarchy
Other DBs
RN: R08893
Genes
AG: BAE07062(btrN)
TaxonomyKoalaUniProt
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
Yokoyama K, Numakura M, Kudo F, Ohmori D, Eguchi T
  Title
Characterization and mechanistic study of a radical SAM dehydrogenase in the biosynthesis of butirosin.
  Journal
J Am Chem Soc 129:15147-55 (2007)
DOI:10.1021/ja072481t
  Sequence

KEGG   ORTHOLOGY: K13548Help
Entry
K13548                      KO                                     

Name
neoA, kanK
Definition
2-deoxy-scyllo-inosamine dehydrogenase [EC:1.1.1.329]
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
    K13548  neoA, kanK; 2-deoxy-scyllo-inosamine dehydrogenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.1  Acting on the CH-OH group of donors
   1.1.1  With NAD+ or NADP+ as acceptor
    1.1.1.329  2-deoxy-scyllo-inosamine dehydrogenase
     K13548  neoA, kanK; 2-deoxy-scyllo-inosamine dehydrogenase
BRITE hierarchy
Other DBs
RN: R08892 R10130
Genes
SRN: A4G23_05130(neoA)
AG: BAD95818(neoA) CAF60530(kanK)
TaxonomyKoalaUniProt
Reference
PMID:16506694 (neoA)
  Authors
Kudo F, Yamamoto Y, Yokoyama K, Eguchi T, Kakinuma K
  Title
Biosynthesis of 2-deoxystreptamine by three crucial enzymes in Streptomyces fradiae NBRC 12773.
  Journal
J Antibiot (Tokyo) 58:766-74 (2005)
DOI:10.1038/ja.2005.104
  Sequence
Reference
PMID:15313224 (kanK)
  Authors
Kharel MK, Subba B, Basnet DB, Woo JS, Lee HC, Liou K, Sohng JK
  Title
A gene cluster for biosynthesis of kanamycin from Streptomyces kanamyceticus: comparison with gentamicin biosynthetic gene cluster.
  Journal
Arch Biochem Biophys 429:204-14 (2004)
DOI:10.1016/j.abb.2004.06.009
  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

KEGG   ENZYME: 1.1.1.329Help
Entry
EC 1.1.1.329                Enzyme                                 

Name
2-deoxy-scyllo-inosamine dehydrogenase;
neoA (gene name);
kanK (gene name, ambiguous);
kanE (gene name, ambiguous)
Class
Oxidoreductases;
Acting on the CH-OH group of donors;
With NAD+ or NADP+ as acceptor
BRITE hierarchy
Sysname
2-deoxy-scyllo-inosamine:NAD(P)+ 1-oxidoreductase
Reaction(IUBMB)
2-deoxy-scyllo-inosamine + NAD(P)+ = 3-amino-2,3-dideoxy-scyllo-inosose + NAD(P)H + H+ [RN:R08892 R10130]
Reaction(KEGG)
Substrate
2-deoxy-scyllo-inosamine [CPD:C17580];
NAD+ [CPD:C00003];
NADP+ [CPD:C00006]
Product
3-amino-2,3-dideoxy-scyllo-inosose [CPD:C17581];
NADH [CPD:C00004];
NADPH [CPD:C00005];
H+ [CPD:C00080]
Comment
Requires zinc. Involved in the biosynthetic pathways of several clinically important aminocyclitol antibiotics, including kanamycin, neomycin and ribostamycin. cf. EC 1.1.99.38, 2-deoxy-scyllo-inosamine dehydrogenase (AdoMet-dependent).
History
EC 1.1.1.329 created 2012
Pathway
ec00524  Neomycin, kanamycin and gentamicin biosynthesis
ec01130  Biosynthesis of antibiotics
Orthology
K13548  2-deoxy-scyllo-inosamine dehydrogenase
Genes
SRN: A4G23_05130(neoA)
Taxonomy
Reference
1  [PMID:16506694]
  Authors
Kudo F, Yamamoto Y, Yokoyama K, Eguchi T, Kakinuma K.
  Title
Biosynthesis of 2-deoxystreptamine by three crucial enzymes in Streptomyces fradiae NBRC 12773.
  Journal
J Antibiot (Tokyo) 58:766-74 (2005)
DOI:10.1038/ja.2005.104
  Sequence
Reference
2  [PMID:19466609]
  Authors
Nepal KK, Oh TJ, Sohng JK
  Title
Heterologous production of paromamine in Streptomyces lividans TK24 using kanamycin biosynthetic genes from Streptomyces kanamyceticus ATCC12853.
  Journal
Mol Cells 27:601-8 (2009)
DOI:10.1007/s10059-009-0080-5
Other DBs
ExplorEnz - The Enzyme Database: 1.1.1.329
IUBMB Enzyme Nomenclature: 1.1.1.329
ExPASy - ENZYME nomenclature database: 1.1.1.329
BRENDA, the Enzyme Database: 1.1.1.329

KEGG   ENZYME: 1.1.99.38Help
Entry
EC 1.1.99.38                Enzyme                                 

Name
2-deoxy-scyllo-inosamine dehydrogenase (AdoMet-dependent);
btrN (gene name);
2-deoxy-scyllo-inosamine dehydrogenase (SAM-dependent)
Class
Oxidoreductases;
Acting on the CH-OH group of donors;
With unknown physiological acceptors
BRITE hierarchy
Sysname
2-deoxy-scyllo-inosamine:S-adenosyl-L-methionine 1-oxidoreductase
Reaction(IUBMB)
2-deoxy-scyllo-inosamine + S-adenosyl-L-methionine = 3-amino-2,3-dideoxy-scyllo-inosose + 5'-deoxyadenosine + L-methionine [RN:R08893]
Reaction(KEGG)
Substrate
2-deoxy-scyllo-inosamine [CPD:C17580];
S-adenosyl-L-methionine [CPD:C00019]
Product
3-amino-2,3-dideoxy-scyllo-inosose [CPD:C17581];
5'-deoxyadenosine [CPD:C05198];
L-methionine [CPD:C00073]
Comment
Involved in the biosynthetic pathway of the aminoglycoside antibiotics of the butirosin family. The enzyme from Bacillus circulans was shown to be a radical S-adenosyl-L-methionine (SAM) enzyme. cf. EC 1.1.1.329, 2-deoxy-scyllo-inosamine dehydrogenase.
History
EC 1.1.99.38 created 2012, modified 2013
Pathway
ec00524  Neomycin, kanamycin and gentamicin biosynthesis
ec01130  Biosynthesis of antibiotics
Orthology
K13549  2-deoxy-scyllo-inosamine dehydrogenase (SAM-dependent)
Reference
1  [PMID:18001019]
  Authors
Yokoyama K, Numakura M, Kudo F, Ohmori D, Eguchi T.
  Title
Characterization and mechanistic study of a radical SAM dehydrogenase in the biosynthesis of butirosin.
  Journal
J Am Chem Soc 129:15147-55 (2007)
DOI:10.1021/ja072481t
  Sequence
Reference
2  [PMID:18672902]
  Authors
Yokoyama K, Ohmori D, Kudo F, Eguchi T.
  Title
Mechanistic study on the reaction of a radical SAM dehydrogenase BtrN by electron paramagnetic resonance spectroscopy.
  Journal
Biochemistry 47:8950-60 (2008)
DOI:10.1021/bi800509x
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.1.99.38
IUBMB Enzyme Nomenclature: 1.1.99.38
ExPASy - ENZYME nomenclature database: 1.1.99.38
BRENDA, the Enzyme Database: 1.1.99.38

KEGG   REACTION: R08892Help
Entry
R08892                      Reaction                               

Name
2-deoxy-scyllo-inosamine:NAD+ oxidoreductase
Definition
2-Deoxy-scyllo-inosamine + NAD+ <=> 3-Amino-2,3-dideoxy-scyllo-inosose + NADH + H+
Equation
Reaction class
RC00001  C00003_C00004
RC00154  C17580_C17581
Enzyme
Pathway
rn00524  Neomycin, kanamycin and gentamicin biosynthesis
rn01130  Biosynthesis of antibiotics
Orthology
K13548  2-deoxy-scyllo-inosamine dehydrogenase [EC:1.1.1.329]
Other DBs
RHEA: 33886

KEGG   REACTION: R10130Help
Entry
R10130                      Reaction                               

Name
2-deoxy-scyllo-inosamine:NADP+ 1-oxidoreductase
Definition
2-Deoxy-scyllo-inosamine + NADP+ <=> 3-Amino-2,3-dideoxy-scyllo-inosose + NADPH + H+
Equation
Reaction class
RC00001  C00005_C00006
RC00154  C17580_C17581
Enzyme
Pathway
rn00524  Neomycin, kanamycin and gentamicin biosynthesis
rn01130  Biosynthesis of antibiotics
Orthology
K13548  2-deoxy-scyllo-inosamine dehydrogenase [EC:1.1.1.329]
Other DBs
RHEA: 33882

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