KEGG   PATHWAY: ko00524Help
Entry
ko00524                     Pathway                                

Name
Butirosin and neomycin biosynthesis
Class
Metabolism; Biosynthesis of other secondary metabolites
BRITE hierarchy
Pathway map
Butirosin and neomycin biosynthesis
ko00524

All organismsOrtholog table
Orthology
K00844  
hexokinase [EC:2.7.1.1]
K12407  
glucokinase [EC:2.7.1.2]
K00845  
glucokinase [EC:2.7.1.2]
K13546  
2-deoxy-scyllo-inosose synthase [EC:4.2.3.124]
K13547  
L-glutamine:2-deoxy-scyllo-inosose/3-amino-2,3-dideoxy-scyllo-inosose aminotransferase [EC:2.6.1.101 2.6.1.100]
K13548  
2-deoxy-scyllo-inosamine dehydrogenase [EC:1.1.1.329]
K13549  
2-deoxy-scyllo-inosamine dehydrogenase (SAM-dependent) [EC:1.1.99.38]
K13550  
2-deoxystreptamine N-acetyl-D-glucosaminyltransferase / 2-deoxystreptamine glucosyltransferase [EC:2.4.1.284 2.4.1.283]
K13551  
2'-N-acetylparomamine deacetylase [EC:3.5.1.112]
K17078  
2'-N-acetylparomamine deacetylase / 2'''-acetyl-6'''-hydroxyneomycin deacetylase [EC:3.5.1.113 3.5.1.112]
K13552  
paromamine 6'-oxidase / 6'''-hydroxyneomycin C oxidase / 2'-deamino-2'-hydroxyparomamine 6'-oxidase [EC:1.1.3.- 1.1.3.44 1.1.3.43]
K13553  
neamine transaminase / 2'-deamino-2'-hydroxyneamine transaminase / neomycin C transaminase [EC:2.6.1.95 2.6.1.94 2.6.1.93]
K13554  
neamine phosphoribosyltransferase [EC:2.4.2.49]
K13555  
5''-phosphoribostamycin phosphatase [EC:3.1.3.88]
K13556  
UDP-N-acetyl-D-glucosamine:ribostamycin N-acetyl-D-glucosaminyltransferase [EC:2.4.1.285]
K13559  
[BtrI acyl-carrier protein]--L-glutamate ligase [EC:6.2.1.39]
K13560  
L-glutamyl-[BtrI acyl-carrier protein] decarboxylase [EC:4.1.1.95]
K13561  
4-(gamma-L-glutamylamino)butanoyl-[BtrI acyl-carrier protein] monooxygenase [EC:1.14.14.13]
K13562  
NAD(P)H:FMN oxidoreductase [EC:1.5.1.-]
K13563  
ribostamycin:4-(gamma-L-glutamylamino)-(S)-2-hydroxybutanoyl-[BtrI acyl-carrier protein] 4-(gamma-L-glutamylamino)-(S)-2-hydroxybutanoate transferase [EC:2.3.2.19]
K13564  
gamma-L-glutamyl-butirosin B gamma-L-glutamyl cyclotransferase [EC:4.3.2.6]
Compound
C00025  
L-Glutamate
C00031  
D-Glucose
C00043  
UDP-N-acetyl-alpha-D-glucosamine
C00061  
FMN
C00092  
D-Glucose 6-phosphate
C00229  
Acyl-carrier protein
C00304  
Kanamycin
C01441  
Neamine
C01737  
Neomycin B
C01743  
Paromamine
C01759  
Ribostamycin
C01847  
Reduced FMN
C02627  
2-Deoxystreptamine
C15652  
Neomycin C
C17209  
2-Deoxy-scyllo-inosose
C17580  
2-Deoxy-scyllo-inosamine
C17581  
3-Amino-2,3-dideoxy-scyllo-inosose
C17582  
2'-N-Acetylparomamine
C17583  
6'-Dehydro-6'-oxoparomamine
C17585  
Butirosin A
C17586  
Butirosin B
C17587  
2'''-N-Acetyl-6'''-deamino-6'''-hydroxyneomycin C
C17588  
6'''-Deamino-6'''-hydroxyneomycin C
C17589  
6'''-Deamino-6'''-oxoneomycin C
C18004  
5''-Phosphoribostamycin
C18005  
gamma-L-Glutamyl-butirosin B
C18006  
gamma-L-Glutamyl-[acp]
C18007  
4-Aminobutyryl-[acp]
C18008  
4-(gamma-L-Glutamylamino)butanoyl-[acp]
C18009  
4-(gamma-L-Glutamylamino)-(2S)-2-hydroxybutanoyl-[acp]
C20350  
2'-Deamino-2'-hydroxyneamine
C20351  
2'-Deamino-2'-hydroxy-6'-dehydroparomamine
C20353  
2'-Deamino-2'-hydroxyparomamine
Reference
  Authors
Kudo F, Eguchi T
  Title
Biosynthetic enzymes for the aminoglycosides butirosin and neomycin.
  Journal
Methods Enzymol 459:493-519 (2009)
Reference
  Authors
Kudo F, Eguchi T
  Title
Biosynthetic genes for aminoglycoside antibiotics.
  Journal
J Antibiot (Tokyo) 62:471-81 (2009)
Reference
  Authors
Nango E, Kumasaka T, Hirayama T, Tanaka N, Eguchi T
  Title
Structure of 2-deoxy-scyllo-inosose synthase, a key enzyme in the biosynthesis of 2-deoxystreptamine-containing aminoglycoside antibiotics, in complex with a mechanism-based inhibitor and NAD+.
  Journal
Proteins 70:517-27 (2008)
Reference
  Authors
Yokoyama K, Kudo F, Kuwahara M, Inomata K, Tamegai H, Eguchi T, Kakinuma K
  Title
Stereochemical recognition of doubly functional aminotransferase in 2-deoxystreptamine biosynthesis.
  Journal
J Am Chem Soc 127:5869-74 (2005)
Reference
  Authors
Tamegai H, Nango E, Kuwahara M, Yamamoto H, Ota Y, Kuriki H, Eguchi T, Kakinuma K
  Title
Identification of L-glutamine: 2-deoxy-scyllo-inosose aminotransferase required for the biosynthesis of butirosin in Bacillus circulans.
  Journal
J Antibiot (Tokyo) 55:707-14 (2002)
Reference
  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)
Reference
  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)
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)
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)
Reference
  Authors
Fan Q, Huang F, Leadlay PF, Spencer JB
  Title
The neomycin biosynthetic gene cluster of Streptomyces fradiae NCIMB 8233: genetic and biochemical evidence for the roles of two glycosyltransferases and a deacetylase.
  Journal
Org Biomol Chem 6:3306-14 (2008)
Reference
  Authors
Truman AW, Huang F, Llewellyn NM, Spencer JB
  Title
Characterization of the enzyme BtrD from Bacillus circulans and revision of its functional assignment in the biosynthesis of butirosin.
  Journal
Angew Chem Int Ed Engl 46:1462-4 (2007)
Reference
  Authors
Kudo F, Fujii T, Kinoshita S, Eguchi T
  Title
Unique O-ribosylation in the biosynthesis of butirosin.
  Journal
Bioorg Med Chem 15:4360-8 (2007)
Reference
  Authors
Yukita T, Nishida H, Eguchi T, Kakinuma K
  Title
Biosynthesis of (2R)-4-amino-2-hydroxybutyric acid, unique and biologically significant substituent in butirosins.
  Journal
J Antibiot (Tokyo) 56:497-500 (2003)
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)
Reference
  Authors
Llewellyn NM, Li Y, Spencer JB
  Title
Biosynthesis of butirosin: transfer and deprotection of the unique amino acid side chain.
  Journal
Chem Biol 14:379-86 (2007)
Reference
  Authors
Llewellyn NM, Spencer JB
  Title
Chemoenzymatic acylation of aminoglycoside antibiotics.
  Journal
Chem Commun (Camb) 3786-8 (2008)
Reference
  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)
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)

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