KEGG   ORTHOLOGY: K13550Help
Entry
K13550                      KO                                     

Name
btrM, neoD, kanF
Definition
2-deoxystreptamine N-acetyl-D-glucosaminyltransferase / 2-deoxystreptamine glucosyltransferase [EC:2.4.1.283 2.4.1.284]
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
    K13550  btrM, neoD, kanF; 2-deoxystreptamine N-acetyl-D-glucosaminyltransferase / 2-deoxystreptamine glucosyltransferase
Enzymes [BR:ko01000]
 2. Transferases
  2.4  Glycosyltransferases
   2.4.1  Hexosyltransferases
    2.4.1.283  2-deoxystreptamine N-acetyl-D-glucosaminyltransferase
     K13550  btrM, neoD, kanF; 2-deoxystreptamine N-acetyl-D-glucosaminyltransferase / 2-deoxystreptamine glucosyltransferase
    2.4.1.284  2-deoxystreptamine glucosyltransferase
     K13550  btrM, neoD, kanF; 2-deoxystreptamine N-acetyl-D-glucosaminyltransferase / 2-deoxystreptamine glucosyltransferase
BRITE hierarchy
Other DBs
RN: R08894 R10096
Genes
SRN: A4G23_05127(neoD)
AG: BAD95821(neoD) BAE07063(btrM) CAE46947(kanF)
TaxonomyKoalaUniProt
Reference
PMID:16156513 (btrM)
  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
PMID:16506694 (neoD)
  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 (kanF)
  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
Reference
  Authors
Yokoyama K, Yamamoto Y, Kudo F, Eguchi T
  Title
Involvement of two distinct N-acetylglucosaminyltransferases and a dual-function deacetylase in neomycin biosynthesis.
  Journal
Chembiochem 9:865-9 (2008)
DOI:10.1002/cbic.200700717
Reference
  Authors
Park JW, Park SR, Nepal KK, Han AR, Ban YH, Yoo YJ, Kim EJ, Kim EM, Kim D, Sohng JK, Yoon YJ
  Title
Discovery of parallel pathways of kanamycin biosynthesis allows antibiotic manipulation.
  Journal
Nat Chem Biol 7:843-52 (2011)
DOI:10.1038/nchembio.671

KEGG   ENZYME: 2.4.1.283Help
Entry
EC 2.4.1.283                Enzyme                                 

Name
2-deoxystreptamine N-acetyl-D-glucosaminyltransferase;
btrM (gene name);
neoD (gene name);
kanF (gene name)
Class
Transferases;
Glycosyltransferases;
Hexosyltransferases
BRITE hierarchy
Sysname
UDP-N-acetyl-alpha-D-glucosamine:2-deoxystreptamine N-acetyl-D-glucosaminyltransferase
Reaction(IUBMB)
UDP-N-acetyl-alpha-D-glucosamine + 2-deoxystreptamine = UDP + 2'-N-acetylparomamine [RN:R08894]
Reaction(KEGG)
Substrate
UDP-N-acetyl-alpha-D-glucosamine [CPD:C00043];
2-deoxystreptamine [CPD:C02627]
Product
UDP [CPD:C00015];
2'-N-acetylparomamine [CPD:C17582]
Comment
Involved in the biosynthetic pathways of several clinically important aminocyclitol antibiotics, including kanamycin, butirosin, neomycin and ribostamycin. Unlike the enzyme from the bacterium Streptomyces kanamyceticus, which can also accept UDP-D-glucose [2] (cf. EC 2.4.1.284, 2-deoxystreptamine glucosyltransferase), the enzyme from Bacillus circulans can only accept UDP-N-acetyl-alpha-D-glucosamine [1].
History
EC 2.4.1.283 created 2012
Pathway
ec00524  Neomycin, kanamycin and gentamicin biosynthesis
ec01130  Biosynthesis of antibiotics
Orthology
K13550  2-deoxystreptamine N-acetyl-D-glucosaminyltransferase / 2-deoxystreptamine glucosyltransferase
Genes
SRN: A4G23_05127(neoD)
Taxonomy
Reference
1  [PMID:18311744]
  Authors
Yokoyama K, Yamamoto Y, Kudo F, Eguchi T.
  Title
Involvement of two distinct N-acetylglucosaminyltransferases and a dual-function  deacetylase in neomycin biosynthesis.
  Journal
Chembiochem 9:865-9 (2008)
DOI:10.1002/cbic.200700717
  Sequence
Reference
2  [PMID:21983602]
  Authors
Park JW, Park SR, Nepal KK, Han AR, Ban YH, Yoo YJ, Kim EJ, Kim EM, Kim D, Sohng JK, Yoon YJ
  Title
Discovery of parallel pathways of kanamycin biosynthesis allows antibiotic manipulation.
  Journal
Nat Chem Biol 7:843-52 (2011)
DOI:10.1038/nchembio.671
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 2.4.1.283
IUBMB Enzyme Nomenclature: 2.4.1.283
ExPASy - ENZYME nomenclature database: 2.4.1.283
BRENDA, the Enzyme Database: 2.4.1.283

KEGG   REACTION: R08894Help
Entry
R08894                      Reaction                               

Name
UDP-N-acetyl-alpha-D-glucosamine:2-deoxystreptamine N-acetyl-D-glucosaminyltransferase
Definition
UDP-N-acetyl-alpha-D-glucosamine + 2-Deoxystreptamine <=> UDP + 2'-N-Acetylparomamine
Equation
Reaction class
RC00005  C00015_C00043
RC00049  C02627_C17582
Enzyme
Pathway
rn00524  Neomycin, kanamycin and gentamicin biosynthesis
rn01130  Biosynthesis of antibiotics
Orthology
K13550  2-deoxystreptamine N-acetyl-D-glucosaminyltransferase / 2-deoxystreptamine glucosyltransferase [EC:2.4.1.283 2.4.1.284]
Other DBs
RHEA: 33950

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