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Literature summary extracted from

  • Park, J.; Park, S.; Nepal, K.; Han, A.; Ban, Y.; Yoo, Y.; Kim, E.; Kim, E.; Kim, D.; Sohng, J.; Yoon, Y.
    Discovery of parallel pathways of kanamycin biosynthesis allows antibiotic manipulation (2011), Nat. Chem. Biol., 7, 843-852.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.4.1.283 KanF cannot be functionally expressed in Escherichia coli Streptomyces venezuelae
2.4.1.284 KanF cannot be functionally expressed in Escherichia coli Streptomyces kanamyceticus
2.4.1.301 expression in Streptomyces venezuelae. Reconstructed the kanamycin pathway stepwise in a mutant strain of Streptomyces venezuelae lacking the genes for biosynthesis of the native deoxysugar by transplanting plasmids harboring different combinations of putative genes from Streptomyces kanamyceticus in Streptomyces venezuelae and then carrying out biochemical analysis and chemical characterization Streptomyces kanamyceticus
2.6.1.93 expressed in Streptomyces venezuelae strain PAR Streptomyces kanamyceticus
2.6.1.94 expressed in Streptomyces venezuelae strain PAR Streptomyces kanamyceticus

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.4.1.284 0.28
-
 2-deoxystreptamine using UDP-D-glucose as donor, in 100 mM Tris-HCl (pH 7.6), 10 mM MgCl2, 6 mM 2-mercaptoethanol, and 1 mM phenylmethylsulfonyl fluoride, at 30°C Streptomyces kanamyceticus
2.4.1.284 0.32
-
 2-deoxystreptamine using UDP-N-acetyl-alpha-D-glucosamine as donor, in 100 mM Tris-HCl (pH 7.6), 10 mM MgCl2, 6 mM 2-mercaptoethanol, and 1 mM phenylmethylsulfonyl fluoride, at 30°C Streptomyces kanamyceticus
2.4.1.284 0.44
-
 UDP-D-glucose in 100 mM Tris-HCl (pH 7.6), 10 mM MgCl22, 6 mM 2-mercaptoethanol, and 1 mM phenylmethylsulfonyl fluoride, at 30°C Streptomyces kanamyceticus
2.4.1.284 2.54
-
 UDP-N-acetyl-alpha-D-glucosamine in 100 mM Tris-HCl (pH 7.6), 10 mM MgCl2, 6 mM 2-mercaptoethanol, and 1 mM phenylmethylsulfonyl fluoride, at 30°C Streptomyces kanamyceticus
2.4.1.301 0.03
-
 UDP-alpha-D-kanosamine 37°C, pH not specified in the publication, cosubstrate: paromamine Streptomyces kanamyceticus
2.4.1.301 0.05
-
 paromamine 37°C, pH not specified in the publication, cosubstrate: UDP-alpha-D-kanosamine Streptomyces kanamyceticus
2.4.1.301 0.25
-
 paromamine 37°C, pH not specified in the publication, cosubstrate: UDP-alpha-D-glucose Streptomyces kanamyceticus
2.4.1.301 0.26
-
 UDP-alpha-D-glucose 37°C, pH not specified in the publication, cosubstrate: paromamine Streptomyces kanamyceticus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.4.1.301 UDP-alpha-D-kanosamine + 2'-deamino-2'-hydroxyneamine Streptomyces kanamyceticus the enzyme is involved in the biosynthetic pathway of kanamycins UDP + kanamycin A
-
 ?
2.4.1.301 UDP-alpha-D-kanosamine + 2'-deamino-2'-hydroxyparomamine Streptomyces kanamyceticus the enzyme is involved in the biosynthetic pathway of kanamycins UDP + kanamycin X
-
 ?
2.4.1.301 UDP-alpha-D-kanosamine + neamine Streptomyces kanamyceticus the enzyme is involved in the biosynthetic pathway of kanamycins UDP + kanamycin B
-
 ?
2.4.1.301 UDP-alpha-D-kanosamine + paromamine Streptomyces kanamyceticus the enzyme is involved in the biosynthetic pathway of kanamycins UDP + kanamycin C
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.4.1.283 Streptomyces venezuelae
-
-
-
2.4.1.283 Streptomyces venezuelae DOSf
-
-
-
2.4.1.284 Streptomyces kanamyceticus
-
-
-
2.4.1.301 Streptomyces kanamyceticus Q65CC7
-
-
2.6.1.93 Streptomyces kanamyceticus
-
-
-
2.6.1.94 Streptomyces kanamyceticus
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.4.1.283 additional information when incubated with UDP-D-glucose and 2-deoxystreptamine, the enzyme is not able to synthesize 2'-deamino-2'-hydroxyparomamine Streptomyces venezuelae ?
-
 ?
2.4.1.283 additional information when incubated with UDP-D-glucose and 2-deoxystreptamine, the enzyme is not able to synthesize 2'-deamino-2'-hydroxyparomamine Streptomyces venezuelae DOSf ?
-
 ?
2.4.1.283 UDP-N-acetyl-alpha-D-glucosamine + 2-deoxystreptamine
-
 Streptomyces venezuelae UDP + 2'-N-acetylparomamine
-
 ?
2.4.1.283 UDP-N-acetyl-alpha-D-glucosamine + 2-deoxystreptamine
-
 Streptomyces venezuelae DOSf UDP + 2'-N-acetylparomamine
-
 ?
2.4.1.284 UDP-D-glucose + 2-deoxystreptamine best substrate Streptomyces kanamyceticus UDP + 2'-deamino-2'-hydroxyparomamine
-
 ?
2.4.1.284 UDP-N-acetyl-alpha-D-glucosamine + 2-deoxystreptamine reaction of 2.4.1.283, one fifth of the catalytic efficiency with UDP-D-glucose Streptomyces kanamyceticus UDP + 2'-N-acetylparomamine
-
 ?
2.4.1.301 additional information the enzyme can also accept UDP-alpha-D-glucose with lower efficiency Streptomyces kanamyceticus ?
-
 ?
2.4.1.301 UDP-alpha-D-glucose + paromamine paromamine i.e. (1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranoside. UDP-alpha-D-kanosamine is a better glycosyl donor than UDP-alpha-D-glucose Streptomyces kanamyceticus UDP + ?
-
 ?
2.4.1.301 UDP-alpha-D-kanosamine + 2'-deamino-2'-hydroxyneamine the enzyme is involved in the biosynthetic pathway of kanamycins Streptomyces kanamyceticus UDP + kanamycin A
-
 ?
2.4.1.301 UDP-alpha-D-kanosamine + 2'-deamino-2'-hydroxyneamine UDP-alpha-D-kanosamine i.e. uridine 5'-[3-(3-amino-3-deoxy-alpha-D-glucopyranosyl) diphosphate] Streptomyces kanamyceticus UDP + kanamycin A kanamycin A i.e. (1S,2R,3R,4S,6R)-4,6-diamino-3-(6-amino-6-deoxy-alpha-D-glucopyranosyloxy)-2-hydroxycyclohexyl 3-amino-3-deoxy-alpha-D-glucopyranoside ?
2.4.1.301 UDP-alpha-D-kanosamine + 2'-deamino-2'-hydroxyparomamine
-
 Streptomyces kanamyceticus UDP + kanamycin X kanamycin X i.e. (1S,2R,3R,4S,6R)-4,6-diamino-3-(alpha-D-glucopyranosyloxy)-2-hydroxycyclohexyl 3-amino-3-deoxy-alpha-D-glucopyranoside ?
2.4.1.301 UDP-alpha-D-kanosamine + 2'-deamino-2'-hydroxyparomamine the enzyme is involved in the biosynthetic pathway of kanamycins Streptomyces kanamyceticus UDP + kanamycin X
-
 ?
2.4.1.301 UDP-alpha-D-kanosamine + neamine the enzyme is involved in the biosynthetic pathway of kanamycins Streptomyces kanamyceticus UDP + kanamycin B
-
 ?
2.4.1.301 UDP-alpha-D-kanosamine + neamine neamine i.e. (1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl 2,6-diamino-2,6-dideoxy-alpha-D-glucopyranoside Streptomyces kanamyceticus UDP + kanamycin B kanamycin B i.e. (1R,2S,3S,4R,6S)-4,6-diamino-3-(3-amino-3-deoxy-alpha-D-glucopyranosyloxy)-2-hydroxycyclohexyl 2,6-diamino-2,6-dideoxy-alpha-D-glucopyranoside ?
2.4.1.301 UDP-alpha-D-kanosamine + paromamine the enzyme is involved in the biosynthetic pathway of kanamycins Streptomyces kanamyceticus UDP + kanamycin C
-
 ?
2.4.1.301 UDP-alpha-D-kanosamine + paromamine paromamine i.e. (1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranoside Streptomyces kanamyceticus UDP + kanamycin C kanamycin C i.e. (1R,2S,3S,4R,6S)-4,6-diamino-3-(3-amino-3-deoxy-alpha-D-glucopyranosyloxy)-2-hydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranoside ?
2.6.1.93 6'-dehydroparomamine + L-glutamate
-
 Streptomyces kanamyceticus neamine + 2-oxoglutarate
-
 ?
2.6.1.94 2'-deamino-2'-hydroxyparomamine + L-glutamate
-
 Streptomyces kanamyceticus 2'-deamino-2'-hydroxyneamine + 2-oxoglutarate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.4.1.283 btrM
-
 Streptomyces venezuelae
2.4.1.283 neoD
-
 Streptomyces venezuelae
2.4.1.284 kanF
-
 Streptomyces kanamyceticus
2.4.1.301 KanE
-
 Streptomyces kanamyceticus
2.6.1.93 6'-oxoparomamine aminotransferase
-
 Streptomyces kanamyceticus
2.6.1.93 kacL
-
 Streptomyces kanamyceticus
2.6.1.94 6'-oxoparomamine aminotransferase
-
 Streptomyces kanamyceticus
2.6.1.94 kacL
-
 Streptomyces kanamyceticus

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.4.1.284 0.29
-
 UDP-D-glucose in 100 mM Tris-HCl (pH 7.6), 10 mM MgCl2, 6 mM 2-mercaptoethanol, and 1 mM phenylmethylsulfonyl fluoride, at 30°C Streptomyces kanamyceticus
2.4.1.284 0.33
-
 UDP-N-acetyl-alpha-D-glucosamine in 100 mM Tris-HCl (pH 7.6), 10 mM MgCl2, 6 mM 2-mercaptoethanol, and 1 mM phenylmethylsulfonyl fluoride, at 30°C Streptomyces kanamyceticus
2.4.1.301 0.053
-
 UDP-alpha-D-glucose 37°C, pH not specified in the publication Streptomyces kanamyceticus
2.4.1.301 0.056
-
 UDP-alpha-D-kanosamine 37°C, pH not specified in the publication Streptomyces kanamyceticus

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
2.4.1.284 0.13
-
 UDP-N-acetyl-alpha-D-glucosamine in 100 mM Tris-HCl (pH 7.6), 10 mM MgCl2, 6 mM 2-mercaptoethanol, and 1 mM phenylmethylsulfonyl fluoride, at 30°C Streptomyces kanamyceticus
2.4.1.284 0.66
-
 UDP-D-glucose in 100 mM Tris-HCl (pH 7.6), 10 mM MgCl2, 6 mM 2-mercaptoethanol, and 1 mM phenylmethylsulfonyl fluoride, at 30°C Streptomyces kanamyceticus
2.4.1.301 0.2
-
 UDP-alpha-D-glucose 37°C, pH not specified in the publication, cosubstrate: paromamine Streptomyces kanamyceticus
2.4.1.301 1.87
-
 UDP-alpha-D-kanosamine 37°C, pH not specified in the publication, cosubstrate: paromamine Streptomyces kanamyceticus