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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
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-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-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
reaction mechanism, overview. Once formed, the product undergoes retro oxime-aldol cleavage at the C3'-C40'bond before incorporation into baumycin
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-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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dTDP-beta-L-evernosamine + NADPH + H+ + O2 = dTDP-N-hydroxy-beta-L-evernosamine + NADP+ + H2O
(1a)
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dTDP-beta-L-evernosamine + NADPH + H+ + O2 = dTDP-N-hydroxy-beta-L-evernosamine + NADP+ + H2O
(1a)
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dTDP-beta-L-evernosamine + NADPH + H+ + O2 = dTDP-N-hydroxy-beta-L-evernosamine + NADP+ + H2O
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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
(1b)
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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
(1b)
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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 + 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
TDP-L-epi-vancosamine + 2 NADPH + 2 H+ + 2 O2
? + 2 NADP+ + 3 H2O
additional information
?
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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
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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-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-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-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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?
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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?
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
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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?
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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?
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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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 + 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
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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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?
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Hu, Y.; Al-Mestarihi, A.; Grimes, C.L.; Kahne, D.; Bachmann, B.O.
A unifying nitrososynthase involved in nitrosugar biosynthesis
J. Am. Chem. Soc.
130
15756-15757
2008
Micromonospora carbonacea, Micromonospora carbonacea var. africana
brenda
Vey, J.; Al-Mestarihi, A.; Hu, Y.; Funk, M.; Bachmann, B.; Iverson, T.
Structure and mechanism of ORF36, an amino sugar oxidizing enzyme in everninomicin biosynthesis
Biochemistry
49
9306-9317
2010
Micromonospora carbonacea (B5APQ9), Micromonospora carbonacea ATCC 39149 (B5APQ9)
brenda
Al-Mestarihi, A.; Romo, A.; Liu, H.; Bachmann, B.
Nitrososynthase-triggered oxidative carbon-carbon bond cleavage in baumycin biosynthesis
J. Am. Chem. Soc.
135
11457-11460
2013
Streptomyces peucetius (O33706), Streptomyces peucetius
brenda
Li, Y.; Ding, L.; Zhang, Q.; Wang, W.
MD and QM/MM study on catalytic mechanism of a FAD-dependent enzyme ORF36: For nitro sugar biosynthesis
J. Mol. Graph. Model.
44
9-16
2013
Micromonospora sp. (B5APQ9), Micromonospora sp. ATCC 39149 (B5APQ9)
brenda
Sartor, L.; Ibarra, C.; Al-Mestarihi, A.; Bachmann, B.O.; Vey, J.L.
Structure of DnmZ, a nitrososynthase in the Streptomyces peucetius anthracycline biosynthetic pathway
Acta Crystallogr. Sect. F
71
1205-1214
2015
Streptomyces peucetius (A0A0R4I990), Streptomyces peucetius
brenda
1.14.13.187 L-evernosamine nitrososynthase
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