1.14.13.187: L-evernosamine nitrososynthase
This is an abbreviated version!
For detailed information about L-evernosamine nitrososynthase, go to the full flat file.
Word Map on EC 1.14.13.187
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1.14.13.187
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thymidine
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monooxygenase
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micromonospora
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anthracycline
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flavin-dependent
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africana
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peucetius
- 1.14.13.187
- thymidine
- monooxygenase
- micromonospora
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anthracycline
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flavin-dependent
- africana
- peucetius
Reaction
+ 2 NADPH + 2 H+ + 2 O2 = + 2 NADP+ + 3 H2O
Synonyms
DnmZ, nitrososynthase, ORF36
ECTree
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Substrates Products
Substrates Products on EC 1.14.13.187 - L-evernosamine nitrososynthase
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REACTION DIAGRAM
dTDP-beta-L-evernosamine + 2 NADPH + 2 H+ + 2 O2
dTDP-2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitroso-beta-L-arabino-hexopyranose + 2 NADP+ + 3 H2O
dTDP-beta-L-evernosamine + NADPH + H+ + O2
dTDP-N-hydroxy-beta-L-evernosamine + NADP+ + H2O
dTDP-N-hydroxy-beta-L-evernosamine + NADPH + H+ + O2
dTDP-2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitroso-beta-L-arabino-hexopyranose + NADP+ + 2 H2O
dTDP-2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitroso-beta-L-arabino-hexopyranose + 2 NADP+ + 3 H2O
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overall reaction, dTDP-beta-L-evernosamine i.e. dTDP-3-amino-2,3,6-trideoxy-3-C-methyl-4-O-methyl-beta-L-arabino-hexopyranose. The nitroso group is probably spontaneously oxidized to a nitro group giving dTDP-beta-L-evernitrose, which is involved in the biosynthesis of the antibiotic everninomycin
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dTDP-beta-L-evernosamine + 2 NADPH + 2 H+ + 2 O2
dTDP-2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitroso-beta-L-arabino-hexopyranose + 2 NADP+ + 3 H2O
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overall reaction, dTDP-beta-L-evernosamine i.e. dTDP-3-amino-2,3,6-trideoxy-3-C-methyl-4-O-methyl-beta-L-arabino-hexopyranose. The nitroso group is probably spontaneously oxidized to a nitro group giving dTDP-beta-L-evernitrose, which is involved in the biosynthesis of the antibiotic everninomycin
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dTDP-beta-L-evernosamine + 2 NADPH + 2 H+ + 2 O2
dTDP-2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitroso-beta-L-arabino-hexopyranose + 2 NADP+ + 3 H2O
overall reaction
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?
dTDP-N-hydroxy-beta-L-evernosamine + NADP+ + H2O
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dTDP-beta-L-evernosamine i.e. dTDP-3-amino-2,3,6-trideoxy-3-C-methyl-4-O-methyl-beta-L-arabino-hexopyranose
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?
dTDP-beta-L-evernosamine + NADPH + H+ + O2
dTDP-N-hydroxy-beta-L-evernosamine + NADP+ + H2O
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dTDP-beta-L-evernosamine i.e. dTDP-3-amino-2,3,6-trideoxy-3-C-methyl-4-O-methyl-beta-L-arabino-hexopyranose
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?
dTDP-2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitroso-beta-L-arabino-hexopyranose + NADP+ + 2 H2O
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dTDP-beta-L-evernosamine i.e. dTDP-3-amino-2,3,6-trideoxy-3-C-methyl-4-O-methyl-beta-L-arabino-hexopyranose
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?
dTDP-N-hydroxy-beta-L-evernosamine + NADPH + H+ + O2
dTDP-2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitroso-beta-L-arabino-hexopyranose + NADP+ + 2 H2O
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dTDP-beta-L-evernosamine i.e. dTDP-3-amino-2,3,6-trideoxy-3-C-methyl-4-O-methyl-beta-L-arabino-hexopyranose
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?
? + 2 NADP+ + 3 H2O
analog of TDP-L-evernitrosamine. Molecular oxygen, rather than oxygen from water, is incorporated into intermediates and products
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?
TDP-L-epi-vancosamine + 2 NADPH + 2 H+ + 2 O2
? + 2 NADP+ + 3 H2O
analog of TDP-L-evernitrosamine. Molecular oxygen, rather than oxygen from water, is incorporated into intermediates and products
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?
TDP-L-epi-vancosamine + 2 NADPH + 2 H+ + 2 O2
? + 2 NADP+ + 3 H2O
enzyme catalyzes a two-step-oxidation. For the second oxidation step, three elementary catalytic steps are found, i.e. a hydroxylation step, a hydrogen back-transfer step and a hydroxyl group elimination step. The hydroxylation step is the rate-determining step with an energy barrier of 26.3 kcal/mol. An oxygen atom from the coenzyme FADHOOH is inserted into the product. Groups Gly132/Ala133/Leu134, Met375/Gln376 and a water fence play a key role in facilitating the rate-determining step. Residues Leu160, Val161 and Ser162 are critical to suppress the rate-determining step
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TDP-L-epi-vancosamine + 2 NADPH + 2 H+ + 2 O2
? + 2 NADP+ + 3 H2O
enzyme catalyzes a two-step-oxidation. For the second oxidation step, three elementary catalytic steps are found, i.e. a hydroxylation step, a hydrogen back-transfer step and a hydroxyl group elimination step. The hydroxylation step is the rate-determining step with an energy barrier of 26.3 kcal/mol. An oxygen atom from the coenzyme FADHOOH is inserted into the product. Groups Gly132/Ala133/Leu134, Met375/Gln376 and a water fence play a key role in facilitating the rate-determining step. Residues Leu160, Val161 and Ser162 are critical to suppress the rate-determining step
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?
TDP-L-epi-vancosamine + 2 NADPH + 2 H+ + 2 O2
? + 2 NADP+ + 3 H2O
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the enzyme catalyzes oxidation of TDP-L-epi-vancosamine to its vicinal hydroxy nitroso congener triggers C-C bond cleavage. The overall rearrangement of the hydroxy nitroso sugar to the aldehyde-oxime product is formally that of a retro oxime-aldol transformation
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thymine is recognized by interactions between the C4 carbonyl O atom and Arg332, and between both N3 and the C4 carbonyl O atom and a water molecule that hydrogen-bonds to the backbone carbonyl of Ala322. The ribose 3' hydroxyl group is hydrogen-bonded by Glu117, which is suitably positioned to form a salt bridge with Arg243. The dTDP diphosphate makes no apparent interactions with the protein
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additional information
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thymine is recognized by interactions between the C4 carbonyl O atom and Arg332, and between both N3 and the C4 carbonyl O atom and a water molecule that hydrogen-bonds to the backbone carbonyl of Ala322. The ribose 3' hydroxyl group is hydrogen-bonded by Glu117, which is suitably positioned to form a salt bridge with Arg243. The dTDP diphosphate makes no apparent interactions with the protein
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