MetaCyc Reaction:

Superclasses: Reactions Classified By Conversion Type Simple Reactions Chemical Reactions
Reactions Classified By Substrate Small-Molecule Reactions

EC Number:

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

Most BioCyc compounds have been protonated to a reference pH value of 7.3, and some reactions have been computationally balanced for hydrogen by adding free protons. Please see the PGDB Concepts Guide for more information.

Mass balance status: Balanced.

Enzyme Commission Primary Name: tropine acyltransferase

Enzyme Commission Synonyms: tropine:acyl-CoA transferase, acetyl-CoA:tropan-3-ol acyltransferase, tropine acetyltransferase, tropine tigloyltransferase, TAT

Standard Gibbs Free Energy (ΔrG in kcal/mol): 178.27905 Inferred by computational analysis [Latendresse13]

Enzyme Commission Summary:
This enzyme exhibits absolute specificity for the endo/3α configuration found in tropine as pseudotropine (tropan-3β-ol; see EC, pseudotropine acyltransferase) is not a substrate [Boswell99]. 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 [Li06b].

Citations: [Robins91, Robins94]

Unification Links: Rhea:25516

Relationship Links: BRENDA:EC: , ENZYME:EC: , IUBMB-ExplorEnz:EC:


Boswell99: Boswell HD, Drager B, McLauchlan WR, Portsteffen A, Robins DJ, Robins RJ, Walton NJ (1999). "Specificities of the enzymes of N-alkyltropane biosynthesis in Brugmansia and Datura." Phytochemistry 52(5);871-8. PMID: 10626376

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Li06b: Li R, Reed DW, Liu E, Nowak J, Pelcher LE, Page JE, Covello PS (2006). "Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement." Chem Biol 13(5);513-20. PMID: 16720272

Robins91: Robins RJ, Bachmann P, Robinson T, Rhodes MJ, Yamada Y (1991). "The formation of 3 alpha- and 3 beta-acetoxytropanes by Datura stramonium transformed root cultures involves two acetyl-CoA-dependent acyltransferases." FEBS Lett 292(1-2);293-7. PMID: 1959620

Robins94: Robins RJ, Bachmann P, Peerless AC, Rabot S (1994). "Esterification reactions in the biosynthesis of tropane alkaloids in transformed root cultures." Plant Cell, Tissue Organ Cult. 38 241-247.

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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