KEGG   ENZYME: 2.3.1.185
Entry
EC 2.3.1.185                Enzyme                                 
Name
tropine acyltransferase;
tropine:acyl-CoA transferase;
acetyl-CoA:tropan-3-ol acyltransferase;
tropine acetyltransferase;
tropine tigloyltransferase;
TAT
Class
Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups
Sysname
acyl-CoA:tropine O-acyltransferase
Reaction(IUBMB)
an acyl-CoA + tropine = CoA + an O-acyltropine [RN:R08712]
Reaction(KEGG)
R08712 > R06735
Substrate
acyl-CoA [CPD:C00040];
tropine [CPD:C00729]
Product
CoA [CPD:C00010];
O-acyltropine [CPD:C02089]
Comment
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].
History
EC 2.3.1.185 created 2008
Pathway
ec00960  Tropane, piperidine and pyridine alkaloid biosynthesis
Reference
1  [PMID:1959620]
  Authors
Robins RJ, Bachmann P, Robinson T, Rhodes MJ, Yamada Y.
  Title
The formation of 3 alpha- and 3 beta-acetoxytropanes by Datura stramonium transformed root cultures involves two acetyl-CoA-dependent acyltransferases.
  Journal
FEBS Lett 292:293-7 (1991)
DOI:10.1016/0014-5793(91)80887-9
Reference
2
  Authors
Robins, R.J., Bachmann,P., Peerless, A.C.J. and Rabot, S.
  Title
Esterification reactions in the biosynthesis of tropane alkaloids in transformed root cultures.
  Journal
Plant Cell, Tissue Organ Cult 38:241-247 (1994)
Reference
3  [PMID:10626376]
  Authors
Boswell HD, Drager B, McLauchlan WR, Portsteffen A, Robins DJ, Robins RJ, Walton NJ.
  Title
Specificities of the enzymes of N-alkyltropane biosynthesis in Brugmansia and Datura.
  Journal
Phytochemistry 52:871-8 (1999)
DOI:10.1016/S0031-9422(99)00293-9
Reference
4  [PMID:16720272]
  Authors
Li R, Reed DW, Liu E, Nowak J, Pelcher LE, Page JE, Covello PS.
  Title
Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement.
  Journal
Chem Biol 13:513-20 (2006)
DOI:10.1016/j.chembiol.2006.03.005
Other DBs
ExplorEnz - The Enzyme Database: 2.3.1.185
IUBMB Enzyme Nomenclature: 2.3.1.185
ExPASy - ENZYME nomenclature database: 2.3.1.185
BRENDA, the Enzyme Database: 2.3.1.185
CAS: 138440-79-6 162535-29-7

  All links  
Pathway (2)   
   KEGG PATHWAY (2)   
Chemical substance (6)   
   KEGG COMPOUND (6)   
Chemical reaction (4)   
   KEGG REACTION (2)   
   KEGG RCLASS (2)   
All databases (12)   

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