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EC Tree
The expected taxonomic range for this enzyme is: Micromonospora echinospora
Synonyms
GenK, gentamicin C-methyltransferase,
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gentamicin C-methyltransferase
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2 S-adenosyl-L-methionine + gentamicin X2 = S-adenosyl-L-homocysteine + G418 + 5'-deoxyadenosine + L-methionine
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S-adenosyl-L-methionine:gentamicin X2-methyltransferase
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S-adenosyl-L-methionine + 2'-deamino-2'-hydroxy-gentamicin X2
S-adenosyl-L-homocysteine + ?
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S-adenosyl-L-methionine + gentamicin A
S-adenosyl-L-homocysteine + ?
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S-adenosyl-L-methionine + gentamicin A2
S-adenosyl-L-homocysteine + ?
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S-adenosyl-L-methionine + gentamicin B
S-adenosyl-L-homocysteine + ?
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S-adenosyl-L-methionine + gentamicin X2
S-adenosyl-L-homocysteine + G418
S-adenosyl-L-methionine + JI-20A
S-adenosyl-L-homocysteine + ?
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additional information
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S-adenosyl-L-methionine + gentamicin X2
S-adenosyl-L-homocysteine + G418
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S-adenosyl-L-methionine + gentamicin X2
S-adenosyl-L-homocysteine + G418
best substrate
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additional information
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1 equivalent each of 5'-deoxyadenosine and S-adenosyl-homocysteine are produced for each methylation reaction catalyzed by GenK. The S-methyl group from S-adenosyl-L-methionine is transferred to cobalamin and the aminoglycoside product during the course of the reaction. H atom abstraction from C6' of GenX2 is stereoselective for the pro-R site
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additional information
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no substrates: 6'-fluorogentamicin X2, 6'-O-methylgentamicin X2, 5'-fluorogentamicin X2
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additional information
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no substrates: pseudodisaccharides paromamine, neamine
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S-adenosyl-L-methionine + gentamicin X2
S-adenosyl-L-homocysteine + G418
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4Fe-4S-center
enzyme harbors a single [4Fe-4S] cluster per monomer. 3.5 equivalents of iron and 3.8 equivalents of sulfide are bound to each GenK monomer
methylcobalamin
activity is nearly maximized in the presence of 1 mM methylcobalamin
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6'-fluorogentamicin X2
weak inhibition
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UniProt
brenda
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physiological function
enzyme catalyzes methylation of the 6'-carbon of gentamicin X2 (GenX2) to produce G418 during the biosynthesis of gentamicins. The 6'-pro-R-hydrogen atom of GenX2 is stereoselectively abstracted by the 5'-dAdo· radical and methylation occurs with retention of configuration at C6'. In A model of GenK catalysis free rotation of the radical-bearing carbon is prevented and the radical SAM machinery sits adjacent rather than opposite to the Me-Cbl cofactor with respect to the substrate in the enzyme active site
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A0A0K0K526_MICEC
638
0
69229
TrEMBL
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expression in Escherichia coli
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Kim, H.J.; McCarthy, R.M.; Ogasawara, Y.; Liu, Y.; Mansoorabadi, S.O.; LeVieux, J.; Liu, H.
GenK-catalyzed C-6' methylation in the biosynthesis of gentamicin isolation and characterization of a cobalamin-dependent radical SAM enzyme
J. Am. Chem. Soc.
135
8093-8096
2013
Micromonospora echinospora (A0A0K0K526)
brenda
Kim, H.J.; Liu, Y.N.; McCarty, R.M.; Liu, H.W.
Reaction catalyzed by GenK, a cobalamin-dependent radical S-adenosyl-L-methionine methyltransferase in the biosynthetic pathway of gentamicin, proceeds with retention of configuration
J. Am. Chem. Soc.
139
16084-16087
2017
Micromonospora echinospora (A0A0K0K526)
brenda
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2.1.1.B120 gentamin X2 methyltransferase
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