Entry
Name
Neomycin, kanamycin and gentamicin biosynthesis - Lutra lutra (Eurasian river otter)
Class
Metabolism; Biosynthesis of other secondary metabolites
BRITE hierarchy
Pathway map
llv00524 Neomycin, kanamycin and gentamicin biosynthesis
Drug
Other DBs
Organism
Lutra lutra (Eurasian river otter) [GN:
llv ]
Gene
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
llv00520 Amino sugar and nucleotide sugar metabolism
KO pathway