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1,3,7-trimethylxanthine + O2 + NAD(P)H + H+
3,7-dimethylxanthine + formaldehyde + NAD(P)+
-
i.e. caffeine
i.e. theobromine
-
?
1,3,7-trimethylxanthine + O2 + NADPH + H+
1,3-dimethylxanthine + formaldehyde + NADP+ + H2O
-
i.e. caffeine
i.e. theophylline
-
?
1,3,7-trimethylxanthine + O2 + NADPH + H+
1,7-dimethylxanthine + formaldehyde + NADP+ + H2O
-
i.e. caffeine
i.e. paraxanthine
-
?
1,7-dimethylxanthine + 2 O2 + 2 NADH + 2 H+
xanthine + 2 NAD+ + 2 H2O + 2 formaldehyde
1,7-dimethylxanthine + 2 O2 + 2 NADPH + 2 H+
xanthine + 2 NADP+ + 2 H2O + 2 formaldehyde
1,7-dimethylxanthine + O2 + NADH + H+
7-methylxanthine + NAD+ + H2O + formaldehyde
1,7-dimethylxanthine + O2 + NADPH + H+
7-methylxanthine + NADP+ + H2O + formaldehyde
-
i.e. paraxanthine, activity of the reductase component of the N-demethylase holoenzyme (Ccr) with NADPH is 22% of that with NADH. The enzyme also catalyzes the further demethylation of the product 7-methylxanthine to xanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
3,7-dimethylxanthine + O2 + NAD(P)H + H+
monomethylxanthine + formaldehyde + NADP+
-
theobromine demethylase
-
-
?
3-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
-
3-methylxanthine demethylation is 12% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
7-methylxanthine + O2 + NAD(P)H + H+
xanthine + formaldehyde + NADP+
-
heteroxanthine demethylase, substrate-selective
-
-
?
7-methylxanthine + O2 + NAD(P)H + H+
xanthine + NAD(P)+ + H2O + formaldehyde
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
7-methylxanthine + O2 + NADPH + H+
xanthine + NADP+ + H2O + formaldehyde
-
-
-
-
?
caffeine + 2 O2 + 2 NADH + 2 H+
7-methylxanthine + 2 NAD+ + 2 H2O + 2 formaldehyde
-
i.e. 1,3,7-trimethylxanthine. Caffeine demethylation is 7% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
caffeine + 3 O2 + 3 NADH + 3 H+
xanthine + 3 NAD+ + 3 H2O + 3 formaldehyde
-
i.e. 1,3,7-trimethylxanthine. Caffeine demethylation is 7% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
caffeine + O2 + NADH + H+
1,7-dimethylxanthine + NAD+ + H2O + formaldehyde
-
i.e. 1,3,7-trimethylxanthine. Caffeine demethylation is 7% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
caffeine + O2 + NADH + H+
theobromine + NAD+ + H2O + formaldehyde
theobromine + 2 O2 + 2 NADH + 2 H+
xanthine + 2 NAD+ + 2 H2O + 2 formaldehyde
-
i.e. 3,7-dimethylxanthine. Theobromine demethylation is 13% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
theobromine + O2 + NADH + H+
3-methylxanthine + NAD+ + H2O + formaldehyde
-
i.e. 3,7-dimethylxanthine. Theobromine demethylation is 13% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
theobromine + O2 + NADH + H+
7-methylxanthine + NAD+ + H2O + formaldehyde
-
i.e. 3,7-dimethylxanthine. Theobromine demethylation is 13% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
theophylline + 2 O2 + 2 NADH + 2 H+
xanthine + 2 NAD+ + 2 H2O + 2 formaldehyde
-
1,3-dimethylxanthine. Theophylline demethylation is 3% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
theophylline + O2 + NADH + H+
1-methylxanthine + NAD+ + H2O + formaldehyde
-
1,3-dimethylxanthine. Theophylline demethylation is 3% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
theophylline + O2 + NADH + H+
3-methylxanthine + NAD+ + H2O + formaldehyde
additional information
?
-
1,7-dimethylxanthine + 2 O2 + 2 NADH + 2 H+

xanthine + 2 NAD+ + 2 H2O + 2 formaldehyde
-
i.e. paraxanthine, NADH is the preferred cofactor of reductase component of the N-demethylase holoenzyme (Ccr). The product 7-methylxanthine is further demethylated to xanthine. 1,7-Dimethylxanthine (paraxanthine) demethylation is 22% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
1,7-dimethylxanthine + 2 O2 + 2 NADH + 2 H+
xanthine + 2 NAD+ + 2 H2O + 2 formaldehyde
-
i.e. paraxanthine, NADH is the preferred cofactor of reductase component of the N-demethylase holoenzyme (Ccr). The product 7-methylxanthine is further demethylated to xanthine. 1,7-Dimethylxanthine (paraxanthine) demethylation is 22% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
1,7-dimethylxanthine + 2 O2 + 2 NADPH + 2 H+

xanthine + 2 NADP+ + 2 H2O + 2 formaldehyde
-
i.e. paraxanthine, activity of the reductase component of the N-demethylase holoenzyme (Ccr) with NADPH is 22% of that with NADH. The enzyme also catalyzes the further demethylation of the product 7-methylxanthine to xanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
1,7-dimethylxanthine + 2 O2 + 2 NADPH + 2 H+
xanthine + 2 NADP+ + 2 H2O + 2 formaldehyde
-
i.e. paraxanthine, activity of the reductase component of the N-demethylase holoenzyme (Ccr) with NADPH is 22% of that with NADH. The enzyme also catalyzes the further demethylation of the product 7-methylxanthine to xanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
1,7-dimethylxanthine + O2 + NADH + H+

7-methylxanthine + NAD+ + H2O + formaldehyde
-
i.e. paraxanthine, NADH is the preferred cofactor of reductase component of the N-demethylase holoenzyme (Ccr). The product 7-methylxanthine is further demethylated to xanthine. 1,7-Dimethylxanthine (paraxanthine) demethylation is 22% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
1,7-dimethylxanthine + O2 + NADH + H+
7-methylxanthine + NAD+ + H2O + formaldehyde
-
i.e. paraxanthine, NADH is the preferred cofactor of reductase component of the N-demethylase holoenzyme (Ccr). The product 7-methylxanthine is further demethylated to xanthine. 1,7-Dimethylxanthine (paraxanthine) demethylation is 22% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
7-methylxanthine + O2 + NAD(P)H + H+

xanthine + NAD(P)+ + H2O + formaldehyde
-
part of the caffeine degradation pathway in Pseudomonas putida
-
-
?
7-methylxanthine + O2 + NAD(P)H + H+
xanthine + NAD(P)+ + H2O + formaldehyde
-
part of the caffeine degradation pathway in Pseudomonas putida
-
-
?
7-methylxanthine + O2 + NADH + H+

xanthine + NAD+ + H2O + formaldehyde
-
-
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
-
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
specific substrate
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
-
the enzyme most actively demethylates 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
the N7-demethylation reaction absolutely requires a unique, tightly bound protein complex composed of NdmC, NdmD, and NdmE. NdmE functions as a noncatalytic subunit that serves a structural role in the complexation of the oxygenase (NdmC) and Rieske domains (NdmD)
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
-
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
specific substrate
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
the N7-demethylation reaction absolutely requires a unique, tightly bound protein complex composed of NdmC, NdmD, and NdmE. NdmE functions as a noncatalytic subunit that serves a structural role in the complexation of the oxygenase (NdmC) and Rieske domains (NdmD)
-
-
?
caffeine + O2 + NADH + H+

theobromine + NAD+ + H2O + formaldehyde
-
-
-
?
caffeine + O2 + NADH + H+
theobromine + NAD+ + H2O + formaldehyde
-
i.e. 1,3,7-trimethylxanthine. Caffeine demethylation is 7% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
caffeine + O2 + NADH + H+
theobromine + NAD+ + H2O + formaldehyde
-
-
-
?
theophylline + O2 + NADH + H+

3-methylxanthine + NAD+ + H2O + formaldehyde
-
-
-
?
theophylline + O2 + NADH + H+
3-methylxanthine + NAD+ + H2O + formaldehyde
-
1,3-dimethylxanthine. Theophylline demethylation is 3% of the activity compared to demethylation of 7-methylxanthine. Activity is absolutely dependent of oxygen as a cosubstrate
-
-
?
theophylline + O2 + NADH + H+
3-methylxanthine + NAD+ + H2O + formaldehyde
-
-
-
?
additional information

?
-
-
Ndm exhibits broad-based activity towards caffeine, theophylline, theobromine, 7-methylxanthine and 3-methylxanthine, all of which are growth substrates for Pseudomonas putida CBB5. Production of xanthine from all of these methylxanthines is confirmed. Ndm is most active on 7-methylxanthine, followed by 1,7-dimethylxanthine (paraxanthine), theobromine, 3-methylxanthine, caffeine and theophylline. Ndm does not catalyse O-demethylation of vanillate or vanillin, even after prolonged incubation
-
-
?
additional information
?
-
-
the metabolite is 1,3-dimethylxanthine, i.e. theophylline, is produced by the demethylation in the 7th position of the purine ring, mainly in fungi, overview
-
-
?
additional information
?
-
-
no activity of the heteroxanthine demethylase, when either caffeine or dimethylxanthines are used as substrates
-
-
?
additional information
?
-
caffeine, paraxanthine, and theobromine are not demethylated by the enzyme
-
-
?
additional information
?
-
no activity toward caffeine or theobromine
-
-
?
additional information
?
-
enzyme NdmA catalyzes NADH-dependent N1-demethylation of caffeine to theobromine and theophylline to 3-methylxanthine, and subsequently to 7-methylxanthine, and xanthine. Theobromine is the major product due to highly selective N1-demethylation caffeine by NdmA. But the minor production of paraxanthine from caffeine is due to slight promiscuity of the NdmA towards the N3-position on the caffeine molecule. Direct N-demethylation of caffeine at the N3 position does not occur appreciably with the three N-demethylases involved in caffeine degradation in CBB5
-
-
?
additional information
?
-
-
Ndm exhibits broad-based activity towards caffeine, theophylline, theobromine, 7-methylxanthine and 3-methylxanthine, all of which are growth substrates for Pseudomonas putida CBB5. Production of xanthine from all of these methylxanthines is confirmed. Ndm is most active on 7-methylxanthine, followed by 1,7-dimethylxanthine (paraxanthine), theobromine, 3-methylxanthine, caffeine and theophylline. Ndm does not catalyse O-demethylation of vanillate or vanillin, even after prolonged incubation
-
-
?
additional information
?
-
enzyme NdmA catalyzes NADH-dependent N1-demethylation of caffeine to theobromine and theophylline to 3-methylxanthine, and subsequently to 7-methylxanthine, and xanthine. Theobromine is the major product due to highly selective N1-demethylation caffeine by NdmA. But the minor production of paraxanthine from caffeine is due to slight promiscuity of the NdmA towards the N3-position on the caffeine molecule. Direct N-demethylation of caffeine at the N3 position does not occur appreciably with the three N-demethylases involved in caffeine degradation in CBB5
-
-
?
additional information
?
-
caffeine, paraxanthine, and theobromine are not demethylated by the enzyme
-
-
?
additional information
?
-
-
caffeine, paraxanthine, and theobromine are not demethylated by the enzyme
-
-
?
additional information
?
-
no activity toward caffeine or theobromine
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
1,3,7-trimethylxanthine + O2 + NAD(P)H + H+
3,7-dimethylxanthine + formaldehyde + NAD(P)+
-
i.e. caffeine
i.e. theobromine
-
?
1,3,7-trimethylxanthine + O2 + NADPH + H+
1,3-dimethylxanthine + formaldehyde + NADP+ + H2O
-
i.e. caffeine
i.e. theophylline
-
?
1,3,7-trimethylxanthine + O2 + NADPH + H+
1,7-dimethylxanthine + formaldehyde + NADP+ + H2O
-
i.e. caffeine
i.e. paraxanthine
-
?
7-methylxanthine + O2 + NAD(P)H + H+
xanthine + NAD(P)+ + H2O + formaldehyde
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
caffeine + O2 + NADH + H+
theobromine + NAD+ + H2O + formaldehyde
additional information
?
-
7-methylxanthine + O2 + NAD(P)H + H+

xanthine + NAD(P)+ + H2O + formaldehyde
-
part of the caffeine degradation pathway in Pseudomonas putida
-
-
?
7-methylxanthine + O2 + NAD(P)H + H+
xanthine + NAD(P)+ + H2O + formaldehyde
-
part of the caffeine degradation pathway in Pseudomonas putida
-
-
?
7-methylxanthine + O2 + NADH + H+

xanthine + NAD+ + H2O + formaldehyde
-
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
specific substrate
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
the N7-demethylation reaction absolutely requires a unique, tightly bound protein complex composed of NdmC, NdmD, and NdmE. NdmE functions as a noncatalytic subunit that serves a structural role in the complexation of the oxygenase (NdmC) and Rieske domains (NdmD)
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
-
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
specific substrate
-
-
?
7-methylxanthine + O2 + NADH + H+
xanthine + NAD+ + H2O + formaldehyde
the N7-demethylation reaction absolutely requires a unique, tightly bound protein complex composed of NdmC, NdmD, and NdmE. NdmE functions as a noncatalytic subunit that serves a structural role in the complexation of the oxygenase (NdmC) and Rieske domains (NdmD)
-
-
?
caffeine + O2 + NADH + H+

theobromine + NAD+ + H2O + formaldehyde
-
-
-
?
caffeine + O2 + NADH + H+
theobromine + NAD+ + H2O + formaldehyde
-
-
-
?
additional information

?
-
-
the metabolite is 1,3-dimethylxanthine, i.e. theophylline, is produced by the demethylation in the 7th position of the purine ring, mainly in fungi, overview
-
-
?
additional information
?
-
caffeine, paraxanthine, and theobromine are not demethylated by the enzyme
-
-
?
additional information
?
-
no activity toward caffeine or theobromine
-
-
?
additional information
?
-
enzyme NdmA catalyzes NADH-dependent N1-demethylation of caffeine to theobromine and theophylline to 3-methylxanthine, and subsequently to 7-methylxanthine, and xanthine. Theobromine is the major product due to highly selective N1-demethylation caffeine by NdmA. But the minor production of paraxanthine from caffeine is due to slight promiscuity of the NdmA towards the N3-position on the caffeine molecule. Direct N-demethylation of caffeine at the N3 position does not occur appreciably with the three N-demethylases involved in caffeine degradation in CBB5
-
-
?
additional information
?
-
enzyme NdmA catalyzes NADH-dependent N1-demethylation of caffeine to theobromine and theophylline to 3-methylxanthine, and subsequently to 7-methylxanthine, and xanthine. Theobromine is the major product due to highly selective N1-demethylation caffeine by NdmA. But the minor production of paraxanthine from caffeine is due to slight promiscuity of the NdmA towards the N3-position on the caffeine molecule. Direct N-demethylation of caffeine at the N3 position does not occur appreciably with the three N-demethylases involved in caffeine degradation in CBB5
-
-
?
additional information
?
-
caffeine, paraxanthine, and theobromine are not demethylated by the enzyme
-
-
?
additional information
?
-
-
caffeine, paraxanthine, and theobromine are not demethylated by the enzyme
-
-
?
additional information
?
-
no activity toward caffeine or theobromine
-
-
?
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Glück, M.; Lingens, F.
Heteroxanthinedemethylase, a new enzyme in the degradation of caffeine by Pseudomonas putida
Appl. Microbiol. Biotechnol.
28
59-62
1988
Pseudomonas putida
-
brenda
Summers, R.M.; Louie, T.M.; Yu, C.L.; Subramanian, M.
Characterization of a broad-specificity non-haem iron N-demethylase from Pseudomonas putida CBB5 capable of utilizing several purine alkaloids as sole carbon and nitrogen source
Microbiology
157
583-592
2011
Pseudomonas putida, Pseudomonas putida CBB5
brenda
Dash, S.S.; Gummadi, S.N.
Catabolic pathways and biotechnological applications of microbial caffeine degradation
Biotechnol. Lett.
28
1993-2002
2006
Pseudomonas putida
brenda
Summers, R.M.; Louie, T.M.; Yu, C.L.; Gakhar, L.; Louie, K.C.; Subramanian, M.
Novel, highly specific N-demethylases enable bacteria to live on caffeine and related purine alkaloids
J. Bacteriol.
194
2041-2049
2012
Pseudomonas putida (M1EY73), Pseudomonas putida CBB5 (M1EY73), Pseudomonas putida CBB5
brenda
Summers, R.M.; Seffernick, J.L.; Quandt, E.M.; Yu, C.L.; Barrick, J.E.; Subramanian, M.V.
Caffeine junkie: an unprecedented glutathione S-transferase-dependent oxygenase required for caffeine degradation by Pseudomonas putida CBB5
J. Bacteriol.
195
3933-3939
2013
Pseudomonas putida (M1EY73), Pseudomonas putida CBB5 (M1EY73)
brenda
Algharrawi, K.; Summers, R.; Subramanian, M.
Production of theobromine by N-demethylation of caffeine using metabolically engineered E. coli
Biocatal. Agricult. Biotechnol.
11
153-160
2017
Pseudomonas putida (H9N289), Pseudomonas putida CBB5 (H9N289)
-
brenda