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IUBMB Comments The enzyme from the plant Erythroxylum coca catalyses the penultimate step in the biosynthesis of cocaine. In vivo the reaction proceeds in the opposite direction. With NADH instead of NADPH the reaction rate is reduced to 14%. The enzyme also reduces tropinone, nortropinone and 6-hydroxytropinone but with lower reaction rates.
Synonyms
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ecgonine methyl ester + NADP+ = ecgonone methyl ester + NADPH + H+
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-
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-
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MetaCyc
cocaine biosynthesis
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ecgonine methyl ester:NADP+ oxidoreductase
The enzyme from the plant Erythroxylum coca catalyses the penultimate step in the biosynthesis of cocaine. In vivo the reaction proceeds in the opposite direction. With NADH instead of NADPH the reaction rate is reduced to 14%. The enzyme also reduces tropinone, nortropinone and 6-hydroxytropinone but with lower reaction rates.
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6-hydroxytropinone + NADPH + H+
? + NADP+
Substrates: reduction at 45% of the activity with methylecgonone
r
methyl ecgonone + NADH + H+
methyl ecgonine + NAD+
Substrates: NADH can substitute for NADPH with 14% of the activity compared to NADPH
r
methyl ecgonone + NADPH + H+
methyl ecgonine + NADP+
nortropinone + NADPH + H+
? + NADP+
Substrates: reduction at 6% of the activity with methylecgonone
r
tropinone + NADPH + H+
pseudotropine + NADP+
Substrates: reduction at 36% of the activity with methylecgonone
r
additional information
?
-
methyl ecgonone + NADPH + H+
methyl ecgonine + NADP+
Substrates: cocaine biosynthesis
r
methyl ecgonone + NADPH + H+
methyl ecgonine + NADP+
Substrates: -
r
additional information
?
-
Substrates: no reduction of 8-thiabicyclo[3.2.1]octan-3-one, cyclohexanone, cyclooctanone, N-methyl-4-piperidone
?
additional information
?
-
-
Substrates: no reduction of 8-thiabicyclo[3.2.1]octan-3-one, cyclohexanone, cyclooctanone, N-methyl-4-piperidone
?
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methyl ecgonone + NADPH + H+
methyl ecgonine + NADP+
Substrates: cocaine biosynthesis
r
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NADH
14% of the activity with NADPH
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additional information
not activated by monovalent or divalent cations
additional information
-
not activated by monovalent or divalent cations
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Co2+
5 mM, inhibition by less than 30%
Cu2+
5 mM, 8% residual activity
Fe2+
5 mM, inhibition by less than 30%
Zn2+
5 mM, 58% residual activity
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0.151
methyl ecgonine
pH 6.8, temperature not specified in the publication
0.069
methyl ecgonone
pH 6.8, temperature not specified in the publication
0.0009
NADP+
pH 6.8, temperature not specified in the publication
0.0009
NADPH
pH 6.8, temperature not specified in the publication
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0.002673
methyl ecgonine
substrate inhibition, pH 6.8, temperature not specified in the publication
0.001136
methyl ecgonone
substrate inhibition, pH 6.8, temperature not specified in the publication
0.506
NADP+
substrate inhibition, pH 6.8, temperature not specified in the publication
0.00248
NADPH
substrate inhibition, pH 6.8, temperature not specified in the publication
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0.0002669
pH 6.8 temperature not specified in the publication
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6.8
reduction of methyl ecgonone
9.8
oxidation of methyl ecgonine
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UniProt
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less than 20% of activity compared to young leaves
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highest activity in young leaves
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of young leaves
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-
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less than 20% of activity compared to young leaves
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additional information
no activity in mature leaves or in roots
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additional information
-
no activity in mature leaves or in roots
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Highest Expressing Human Cell Lines
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Cell Line Links
Gene Links
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MER_ERYCB
327
0
36908
Swiss-Prot
-
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36910
calculated from the amino acid sequence
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25
30 min, more than 30% loss of activity
37
30 min, more than 70% loss of activity
50
30 min, complete inactivation abvoe 50°C
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expressed in Escherichia coli
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Jirschitzka, J.; Schmidt, G.W.; Reichelt, M.; Schneider, B.; Gershenzon, J.; D'Auria, J.C.
Plant tropane alkaloid biosynthesis evolved independently in the Solanaceae and Erythroxylaceae
Proc. Natl. Acad. Sci. USA
109
10304-10309
2012
Erythroxylum coca (E7C196), Erythroxylum coca
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