Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups
BRITE hierarchy

acyl-CoA:tropine O-acyltransferase

an acyl-CoA + tropine = CoA + an O-acyltropine [RN:R08712]

R08712 > R06735
Reaction

acyl-CoA [CPD:C00040];
tropine [CPD:C00729]

This enzyme exhibits absolute specificity for the endo/3alpha configuration found in tropine as pseudotropine (tropan-3beta-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].

EC 2.3.1.185 created 2008

1  [PMID:1959620]

Robins RJ, Bachmann P, Robinson T, Rhodes MJ, Yamada Y.

The formation of 3 alpha- and 3 beta-acetoxytropanes by Datura stramonium transformed root cultures involves two acetyl-CoA-dependent acyltransferases.

FEBS Lett 292:293-7 (1991)
DOI:10.1016/0014-5793(91)80887-9

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 38:241-247 (1994)

3  [PMID:10626376]

Boswell HD, Drager B, McLauchlan WR, Portsteffen A, Robins DJ, Robins RJ, Walton NJ.

Specificities of the enzymes of N-alkyltropane biosynthesis in Brugmansia and Datura.

Phytochemistry 52:871-8 (1999)
DOI:10.1016/S0031-9422(99)00293-9

4  [PMID:16720272]

Li R, Reed DW, Liu E, Nowak J, Pelcher LE, Page JE, Covello PS.

Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement.

Chem Biol 13:513-20 (2006)
DOI:10.1016/j.chembiol.2006.03.005