Entry
Name
Neomycin, kanamycin and gentamicin biosynthesis
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
rn00524 Neomycin, kanamycin and gentamicin biosynthesis
Ortholog table
Other DBs
Reaction
R00299 ATP:D-glucose 6-phosphotransferase
R06586 UDP-3-ketoglucose:L-glutamate aminotransferase
R06594 UDP-glucose:NAD+ 3-oxidoreductase
R08617 D-glucose-6-phosphate phosphate-lyase (2-deoxy-scyllo-inosose-forming)
R08890 L-glutamine:2-deoxy-scyllo-inosose aminotransferase
R08891 L-glutamine:3-amino-2,3-dideoxy-scyllo-inosose aminotransferase
R08892 2-deoxy-scyllo-inosamine:NAD+ oxidoreductase
R08893 2-deoxy-scyllo-inosamine:S-adenosyl-L-methionine 1-oxidoreductase
R08894 UDP-N-acetyl-alpha-D-glucosamine:2-deoxystreptamine N-acetyl-D-glucosaminyltransferase
R08895 2'-N-acetylparomamine hydrolase (acetate-forming)
R08896 paromamine:oxygen 6'-oxidoreductase
R08897 neamine:2-oxoglutarate aminotransferase
R08898 5-phospho-alpha-D-ribose 1-diphosphate:neamine phosphoribosyltransferase
R08899 5''-phosphoribostamycin phosphohydrolase
R08900 UDP-N-acetyl-alpha-D-glucosamine:ribostamycin N-acetyl-D-glucosaminyltransferase
R08901 2'''-acetyl-6'''-hydroxyneomycin-C hydrolase (acetate-forming)
R08902 6'''-deamino-6'''-hydroxyneomycin-C:oxygen 6'''-oxidoreductase
R08903 2-oxoglutarate:neomycin-C aminotransferase
R08904 neomycin-C 5'''-epimerase
R08905 L-glutamate:[acyl-carrier protein] ligase (ADP-forming)
R08906 L-glutamate:4-aminobutyryl-[acp] ligase (ADP-forming)
R08907 gamma-L-glutamyl-[acp] carboxy-lyase (4-aminobutyryl-[acp]-forming)
R08908 4-(gamma-L-glutamylamino)butanoyl-[acp],reduced-FMN:oxygen oxidoreductase
R08909 4-(gamma-L-glutamylamino)-(S)-2-hydroxybutanoyl-[acp]:ribostamycin 4-(gamma-L-glutamylamino)-(S)-2-hydroxybutanoate transferase
R08910 gamma-L-glutamyl-butirosin-B gamma-glutamyl cyclotransferase (5-oxoproline-forming)
R10094 2'-deamino-2'-hydroxyneamine:2-oxoglutarate aminotransferase
R10096 UDP-alpha-D-glucose:2-deoxystreptamine 4-O-alpha-D-glucosyltransferase
R10130 2-deoxy-scyllo-inosamine:NADP+ 1-oxidoreductase
R10207 2'-deamino-2'-hydroxyparomamine:oxygen 6'-oxidoreductase
R10312 kanamycin-B,2-oxoglutarate:oxygen oxidoreductase (deaminating, 2'-hydroxylating)
R10417 kanamycin-A:NADP+ oxidoreductase
R10424 UDP-alpha-D-kanosamine:2'-deamino-2'-hydroxyneamine 1-alpha-D-kanosaminyltransferase
R10425 UDP-alpha-D-kanosamine:neamine 1-alpha-D-kanosaminyltransferase
R10426 UDP-alpha-D-kanosamine:paromamine 1-alpha-D-kanosaminyltransferase
R10427 UDP-alpha-D-kanosamine:2'-deamino-2'-hydroxyparomamine 1-alpha-D-kanosaminyltransferase
R10767 tobramycin:carbamoyl-phosphate ligase (AMP,phosphate-forming)
R10768 kanamycin-A:carbamoyl-phosphate ligase (AMP,phosphate-forming)
R11265 ribostamycin:NAD+ 3''-oxidoreductase
R11266 xylostasin:NADP+ 3''-oxidoreductase
R11267 kanamycin-X:oxygen 6'-oxidoreductase
R11268 kanamycin-C:oxygen 6'-oxidoreductase
R11269 kanamycin-A:2-oxoglutarate aminotransferase
R11270 kanamycin-B:2-oxoglutarate aminotransferase
R11271 UDP-alpha-D-glucose:2'-deamino-2'-hydroxyneamine alpha-D-glucosyltransferase
R11272 UDP-alpha-D-glucose:neamine alpha-D-glucosyltransferase
R11273 lividamine:oxygen 6'-oxidoreductase
R11276 lividamine:NADP+ 4'-oxidoreductase
R11277 nebramine:NADP+ 4'-oxidoreductase
R11278 UDP-alpha-D-kanosamine:nebramine alpha-D-kanosaminyltransferase
R11279 kanamycin-B:carbamoyl-phosphate ligase (AMP,phosphate-forming)
R11280 paromamine:5-phospho-alpha-D-ribose-1-diphosphate phosphoribosyltransferase
R11281 5''-phosphoribosylparomamine phosphohydrolase
R11282 UDP-N-acetyl-alpha-D-glucosamine:5-ribosylparomamine N-acetyl-D-glucosaminyltransferase
R11283 2'''-N-acetyl-6'''-deamino-6'''-hydroxyparomomycin-II hydrolase (acetate-forming)
R11284 6'''-deamino-6'''-hydroxyparomomycin-II:oxygen 6'''-oxidoreductase
R11285 paromomycin-II:2-oxoglutarate aminotransferase
R11286 paromomycin-II 5'''-epimerase
R11288 5'''-epi-lividomycin-B 5'''-epimerase
R11289 UDP-D-xylose:paromamine alpha-D-xylosyltransferase
R11290 gentamicin-A2:NAD+ 3''-oxidoreductase
R11291 3''-dehydro-3''-amino-gentamicin-A2:2-oxoglutarate aminotransferase
R11292 S-adenosyl-L-methionine:3''-dehydro-3''-amino-gentamicin-A2 N-methyltransferase
R11293 S-adenosyl-L-methionine:methylcob(III)alamin:gentamicin-A methyltransferase
R11297 antibiotic-JI-20A:2-oxoglutarate aminotransferase
R11298 antibiotic-JI-20Ba:2-oxoglutarate aminotransferase
R11299 antibiotic-JI-20B:2-oxoglutarate aminotransferase
R13180 S-adenosyl-L-methionine:gentamicin X2 C6'-methyltransferase
Compound
C00043 UDP-N-acetyl-alpha-D-glucosamine
C17580 2-Deoxy-scyllo-inosamine
C17581 3-Amino-2,3-dideoxy-scyllo-inosose
C17583 6'-Dehydro-6'-oxoparomamine
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
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
C20699 6''-O-Carbamoylkanamycin A
C21254 3''-Deamino-3''-hydroxykanamycin B
C21260 5''-Phosphoribosylparomamine
C21261 2'''-N-Acetyl-6'''-deamino-6'''-hydroxyparomomycin II
C21262 6'''-Deamino-6'''-hydroxyparomomycin II
C21263 6'''-Deamino-6'''-oxoparomomycin II
C21266 3''-Amino-3''-deoxygentamicin A2
Reference
Authors
Kudo F, Eguchi T
Title
Biosynthetic enzymes for the aminoglycosides butirosin and neomycin.
Journal
Reference
Authors
Kudo F, Eguchi T
Title
Biosynthetic genes for aminoglycoside antibiotics.
Journal
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
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
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
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
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
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
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
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
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
Reference
Authors
Kudo F, Fujii T, Kinoshita S, Eguchi T
Title
Unique O-ribosylation in the biosynthesis of butirosin.
Journal
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
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
Reference
Authors
Llewellyn NM, Li Y, Spencer JB
Title
Biosynthesis of butirosin: transfer and deprotection of the unique amino acid side chain.
Journal
Reference
Authors
Llewellyn NM, Spencer JB
Title
Chemoenzymatic acylation of aminoglycoside antibiotics.
Journal
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
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
Reference
Authors
Arya DP (ed).
Title
Aminoglycoside antibiotics: From chemical biology to drug discovery
Journal
Wiley-Interscience (2007)
Reference
Authors
Park SR, Park JW, Ban YH, Sohng JK, Yoon YJ
Title
2-Deoxystreptamine-containing aminoglycoside antibiotics: recent advances in the characterization and manipulation of their biosynthetic pathways.
Journal
Reference
Authors
Llewellyn NM, Spencer JB
Title
Biosynthesis of 2-deoxystreptamine-containing aminoglycoside antibiotics.
Journal
Reference
Authors
Kudo F, Eguchi T
Title
Aminoglycoside Antibiotics: New Insights into the Biosynthetic Machinery of Old Drugs.
Journal
Reference
Authors
Takeishi R, Kudo F, Numakura M, Eguchi T
Title
Epimerization at C-3'' in butirosin biosynthesis by an NAD(+) -dependent dehydrogenase BtrE and an NADPH-dependent reductase BtrF.
Journal
Reference
Authors
Lv M, Ji X, Zhao J, Li Y, Zhang C, Su L, Ding W, Deng Z, Yu Y, Zhang Q
Title
Characterization of a C3 Deoxygenation Pathway Reveals a Key Branch Point in Aminoglycoside Biosynthesis.
Journal
Reference
Authors
Clausnitzer D, Piepersberg W, Wehmeier UF
Title
The oxidoreductases LivQ and NeoQ are responsible for the different 6'-modifications in the aminoglycosides lividomycin and neomycin.
Journal
Reference
Authors
Park JW, Hong JS, Parajuli N, Jung WS, Park SR, Lim SK, Sohng JK, Yoon YJ
Title
Genetic dissection of the biosynthetic route to gentamicin A2 by heterologous expression of its minimal gene set.
Journal
Reference
Authors
Huang C, Huang F, Moison E, Guo J, Jian X, Duan X, Deng Z, Leadlay PF, Sun Y
Title
Delineating the biosynthesis of gentamicin x2, the common precursor of the gentamicin C antibiotic complex.
Journal
Reference
Authors
Guo J, Huang F, Huang C, Duan X, Jian X, Leeper F, Deng Z, Leadlay PF, Sun Y
Title
Specificity and promiscuity at the branch point in gentamicin biosynthesis.
Journal
Reference
Authors
Gu Y, Ni X, Ren J, Gao H, Wang D, Xia H
Title
Biosynthesis of Epimers C2 and C2a in the Gentamicin C Complex.
Journal
Reference
Authors
Kim HJ, McCarty RM, Ogasawara Y, Liu YN, Mansoorabadi SO, LeVieux J, Liu HW
Title
GenK-catalyzed C-6' methylation in the biosynthesis of gentamicin: isolation and characterization of a cobalamin-dependent radical SAM enzyme.
Journal
Related pathway
rn00520 Amino sugar and nucleotide sugar metabolism
KO pathway
LinkDB
All DBs