EC |
1.1.1.206 |
Accepted name: |
tropinone reductase I |
Reaction: |
tropine + NADP+ = tropinone + NADPH + H+ |
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For diagram of reaction, click here |
Glossary: |
tropine = 3α-hydroxytropane = tropan-3-endo-ol |
Other name(s): |
tropine dehydrogenase; tropinone reductase (ambiguous); TR-I |
Systematic name: |
tropine:NADP+ 3α-oxidoreductase |
Comments: |
Also oxidizes other tropan-3α-ols, but not the corresponding β-derivatives [1]. This enzyme along with EC 1.1.1.236, tropinone reductase II, represents a branch point in tropane alkaloid metabolism [4]. Tropine (the product of EC 1.1.1.206) is incorporated into hyoscyamine and scopolamine whereas pseudotropine (the product of EC 1.1.1.236) is the first specific metabolite on the pathway to the calystegines [4]. Both enzymes are always found together in any given tropane-alkaloid-producing species, have a common substrate, tropinone, and are strictly stereospecific [3]. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 118390-87-7 |
References: |
1. |
Koelen, K.J. and Gross, G.G. Partial purification and properties of tropine dehydrogenase from root cultures of Datura stramonium. Planta Med. 44 (1982) 227–230. [PMID: 17402126] |
2. |
Couladis, M.M, Friesen, J.B., Landgrebe, M.E. and Leete, E. Enzymes catalysing the reduction of tropinone to tropine and ψ-tropine isolated from the roots of Datura innoxia. Pytochemistry 30 (1991) 801–805. |
3. |
Nakajima, K., Hashimoto, T. and Yamada, Y. Two tropinone reductases with different stereospecificities are short-chain dehydrogenases evolved from a common ancestor. Proc. Natl. Acad. Sci. USA 90 (1993) 9591–9595. [DOI] [PMID: 8415746] |
4. |
Dräger, B. Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism. Phytochemistry 67 (2006) 327–337. [DOI] [PMID: 16426652] |
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[EC 1.1.1.206 created 1984, modified 2007] |
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EC |
1.1.1.236 |
Accepted name: |
tropinone reductase II |
Reaction: |
pseudotropine + NADP+ = tropinone + NADPH + H+ |
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For diagram of reaction, click here |
Glossary: |
pseudotropine = ψ-tropine = 3β-hydroxytropane = tropan-3-exo-ol |
Other name(s): |
tropinone (ψ-tropine-forming) reductase; pseudotropine forming tropinone reductase; tropinone reductase (ambiguous); TR-II |
Systematic name: |
pseudotropine:NADP+ 3-oxidoreductase |
Comments: |
This enzyme along with EC 1.1.1.206, tropine dehydrogenase, represents a branch point in tropane alkaloid metabolism [3]. Tropine (the product of EC 1.1.1.206) is incorporated into hyoscyamine and scopolamine whereas pseudotropine (the product of EC 1.1.1.236) is the first specific metabolite on the pathway to the calystegines [3]. Both enzymes are always found together in any given tropane-alkaloid-producing species, have a common substrate, tropinone, and are strictly stereospecific [2]. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 136111-61-0 |
References: |
1. |
Dräger, B., Hashimoto, T. and Yamada, Y. Purification and characterization of pseudotropine forming tropinone reductase from Hyoscyamus niger root cultures. Agric. Biol. Chem. 52 (1988) 2663–2667. |
2. |
Couladis, M.M, Friesen, J.B., Landgrebe, M.E. and Leete, E. Enzymes catalysing the reduction of tropinone to tropine and ψ-tropine isolated from the roots of Datura innoxia. Pytochemistry 30 (1991) 801–805. |
3. |
Nakajima, K., Hashimoto, T. and Yamada, Y. Two tropinone reductases with different stereospecificities are short-chain dehydrogenases evolved from a common ancestor. Proc. Natl. Acad. Sci. USA 90 (1993) 9591–9595. [DOI] [PMID: 8415746] |
4. |
Dräger, B. Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism. Phytochemistry 67 (2006) 327–337. [DOI] [PMID: 16426652] |
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[EC 1.1.1.236 created 1992, modified 2007] |
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EC
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1.1.1.293
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Deleted entry: | tropinone reductase I. This enzyme was already in the Enzyme List as EC 1.1.1.206, tropine dehydrogenase so EC 1.1.1.293 has been withdrawn at the public-review stage |
[EC 1.1.1.293 created 2007, withdrawn while undergoing public review] |
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EC |
1.1.1.334 |
Accepted name: |
methylecgonone reductase |
Reaction: |
ecgonine methyl ester + NADP+ = ecgonone methyl ester + NADPH + H+ |
Glossary: |
ecgonine methyl ester = 2β-carbomethoxy-3β-tropine = methyl (1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
ecgonone methyl ester = 2β-carbomethoxy-3-tropinone = methyl (1R,2R,5S)-8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate |
Other name(s): |
MecgoR (gene name) |
Systematic name: |
ecgonine methyl ester:NADP+ oxidoreductase |
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. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Jirschitzka, J., Schmidt, G.W., Reichelt, M., Schneider, B., Gershenzon, J. and D'Auria, J.C. Plant tropane alkaloid biosynthesis evolved independently in the Solanaceae and Erythroxylaceae. Proc. Natl. Acad. Sci. USA 109 (2012) 10304–10309. [DOI] [PMID: 22665766] |
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[EC 1.1.1.334 created 2012] |
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EC |
2.3.1.185 |
Accepted name: |
tropine acyltransferase |
Reaction: |
an acyl-CoA + tropine = CoA + an O-acyltropine |
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For diagram of tropane alkaloid biosynthesis, click here |
Glossary: |
tropine = tropan-3α-ol = 3α-hydroxytropane |
Other name(s): |
tropine:acyl-CoA transferase; acetyl-CoA:tropan-3-ol acyltransferase; tropine acetyltransferase; tropine tigloyltransferase; TAT |
Systematic name: |
acyl-CoA:tropine O-acyltransferase |
Comments: |
This enzyme exhibits absolute specificity for the endo/3α configuration found in tropine as pseudotropine (tropan-3β-ol; see EC 2.3.1.186, pseudotropine acyltransferase) is not a substrate [3]. Acts on a wide range of aliphatic acyl-CoA derivatives, with tigloyl-CoA and acetyl-CoA being the best substrates. It is probably involved in the formation of the tropane alkaloid littorine, which is a precursor of hyoscyamine [4]. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 138440-79-6, 162535-29-7 |
References: |
1. |
Robins, R.J., Bachmann, P., Robinson, T., Rhodes, M.J. and Yamada, Y. The formation of 3α- and 3β-acetoxytropanes by Datura stramonium transformed root cultures involves two acetyl-CoA-dependent acyltransferases. FEBS Lett. 292 (1991) 293–297. [DOI] [PMID: 1959620] |
2. |
Robins, R.J., Bachmann,P., Peerless, A.C.J. and Rabot, S. Esterification reactions in the biosynthesis of tropane alkaloids in transformed root cultures. Plant Cell, Tissue Organ Cult. 38 (1994) 241–247. |
3. |
Boswell, H.D., Dräger, B., McLauchlan, W.R., Portsteffen, A., Robins, D.J., Robins, R.J. and Walton, N.J. Specificities of the enzymes of N-alkyltropane biosynthesis in Brugmansia and Datura. Phytochemistry 52 (1999) 871–878. [DOI] [PMID: 10626376] |
4. |
Li, R., Reed, D.W., Liu, E., Nowak, J., Pelcher, L.E., Page, J.E. and Covello, P.S. Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement. Chem. Biol. 13 (2006) 513–520. [DOI] [PMID: 16720272] |
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[EC 2.3.1.185 created 2008] |
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EC |
2.3.1.186 |
Accepted name: |
pseudotropine acyltransferase |
Reaction: |
an acyl-CoA + pseudotropine = CoA + an O-acylpseudotropine |
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For diagram of tropane alkaloid biosynthesis, click here |
Glossary: |
tropine = tropan-3β-ol = 3β-hydroxytropane |
Other name(s): |
pseudotropine:acyl-CoA transferase; tigloyl-CoA:pseudotropine acyltransferase; acetyl-CoA:pseudotropine acyltransferase; pseudotropine acetyltransferase; pseudotropine tigloyltransferase; PAT (ambiguous) |
Systematic name: |
acyl-CoA:pseudotropine O-acyltransferase |
Comments: |
This enzyme exhibits absolute specificity for the exo/3β configuration found in pseudotropine as tropine (tropan-3α-ol; see EC 2.3.1.185, tropine acyltransferase) and nortropine are not substrates [1]. Acts on a wide range of aliphatic acyl-CoA derivatives, including acetyl-CoA, β-methylcrotonyl-CoA and tigloyl-CoA [1]. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 138440-78-5, 162535-26-4 |
References: |
1. |
Rabot, S., Peerless, A.C.J. and Robins, R.J. Tigloyl-CoA:pseudotropine acyltransferase — an enzyme of tropane alkaloid biosynthesis. Phytochemistry 39 (1995) 315–322. |
2. |
Robins, R.J., Bachmann, P., Robinson, T., Rhodes, M.J. and Yamada, Y. The formation of 3α- and 3β-acetoxytropanes by Datura stramonium transformed root cultures involves two acetyl-CoA-dependent acyltransferases. FEBS Lett. 292 (1991) 293–297. [DOI] [PMID: 1959620] |
3. |
Robins, R.J., Bachmann,P., Peerless, A.C.J. and Rabot, S. Esterification reactions in the biosynthesis of tropane alkaloids in transformed root cultures. Plant Cell, Tissue Organ Cult. 38 (1994) 241–247. |
4. |
Boswell, H.D., Dräger, B., McLauchlan, W.R., Portsteffen, A., Robins, D.J., Robins, R.J. and Walton, N.J. Specificities of the enzymes of N-alkyltropane biosynthesis in Brugmansia and Datura. Phytochemistry 52 (1999) 871–878. [DOI] [PMID: 10626376] |
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[EC 2.3.1.186 created 2008] |
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EC |
3.1.1.10 |
Accepted name: |
tropinesterase |
Reaction: |
atropine + H2O = tropine + tropate |
Other name(s): |
tropine esterase; atropinase; atropine esterase |
Systematic name: |
atropine acylhydrolase |
Comments: |
Also acts on cocaine and other tropine esters. |
Links to other databases: |
BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, CAS registry number: 59536-71-9 |
References: |
1. |
Glick, D., Glaubach, S. and Moore, D.H. Azolesterase activities of electrophoretically separated proteins of serum. J. Biol. Chem. 144 (1942) 525–528. |
2. |
Moog, P. and Krisch, K. [The purification and characterization of atropine esterase from rabbit liver microsomes] Hoppe-Seyler's Z. Physiol. Chem. 355 (1974) 529–542. [PMID: 4435736] |
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[EC 3.1.1.10 created 1961, deleted 1972, reinstated 1976] |
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EC |
3.1.1.84 |
Accepted name: |
cocaine esterase |
Reaction: |
cocaine + H2O = ecgonine methyl ester + benzoate |
Glossary: |
ecgonine methyl ester = 2β-carbomethoxy-3β-tropine = methyl (1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate |
Other name(s): |
CocE; hCE2; hCE-2; human carboxylesterase 2 |
Systematic name: |
cocaine benzoylhydrolase |
Comments: |
Rhodococcus sp. strain MB1 and Pseudomonas maltophilia strain MB11L can utilize cocaine as sole source of carbon and energy [2,3]. |
Links to other databases: |
BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, PDB |
References: |
1. |
Gao, D., Narasimhan, D.L., Macdonald, J., Brim, R., Ko, M.C., Landry, D.W., Woods, J.H., Sunahara, R.K. and Zhan, C.G. Thermostable variants of cocaine esterase for long-time protection against cocaine toxicity. Mol. Pharmacol. 75 (2009) 318–323. [DOI] [PMID: 18987161] |
2. |
Bresler, M.M., Rosser, S.J., Basran, A. and Bruce, N.C. Gene cloning and nucleotide sequencing and properties of a cocaine esterase from Rhodococcus sp. strain MB1. Appl. Environ. Microbiol. 66 (2000) 904–908. [DOI] [PMID: 10698749] |
3. |
Britt, A.J., Bruce, N.C. and Lowe, C.R. Identification of a cocaine esterase in a strain of Pseudomonas maltophilia. J. Bacteriol. 174 (1992) 2087–2094. [DOI] [PMID: 1551831] |
4. |
Larsen, N.A., Turner, J.M., Stevens, J., Rosser, S.J., Basran, A., Lerner, R.A., Bruce, N.C. and Wilson, I.A. Crystal structure of a bacterial cocaine esterase. Nat. Struct. Biol. 9 (2002) 17–21. [DOI] [PMID: 11742345] |
5. |
Pindel, E.V., Kedishvili, N.Y., Abraham, T.L., Brzezinski, M.R., Zhang, J., Dean, R.A. and Bosron, W.F. Purification and cloning of a broad substrate specificity human liver carboxylesterase that catalyzes the hydrolysis of cocaine and heroin. J. Biol. Chem. 272 (1997) 14769–14775. [DOI] [PMID: 9169443] |
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[EC 3.1.1.84 created 2010] |
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