ExplorEnz: EC 2.3.1.185

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2.3.1.185

Accepted name:

tropine acyltransferase

Reaction:

an acyl-CoA + tropine = CoA + an O-acyltropine

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]

[EC 2.3.1.185 created 2008]