EC 2.3.1.185 - Tropine acyltransferase

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IntEnz Enzyme Nomenclature
EC 2.3.1.185

Names

Accepted name:
tropine acyltransferase
Other names:
tropine:acyl-CoA transferase
acetyl-CoA:tropan-3-ol acyltransferase
tropine acetyltransferase
tropine tigloyltransferase
TAT
Systematic name:
acyl-CoA:tropine O-acyltransferase

Reaction

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

Enzymes and pathways: NC-IUBMB , BRENDA , ExplorEnz , ENZYME@ExPASy , KEGG , MetaCyc , UniPathway
Structural data: CSA , EC2PDB
CAS Registry Numbers: 138440-79-6 162535-29-7

References

  1. Robins, R.J., Bachmann, P., Robinson, T., Rhodes, M.J.C. 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: 293-297 (1991). [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: 241-247 (1994).
  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: 871-878 (1999). [PMID: 10626376]
  4. Boswell, H.D., Dräger, B., McLauchlan, W.R., Portsteffen, A., Robins, D.J., Robins, R.J. and Walton, N.J.
    Erratum report. Specificities of the enzymes of N-alkyltropane biosynthesis in Brugmansia and Datura.
    Phytochemistry 54: 449 (2000).
  5. 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: 513-520 (2006). [PMID: 16720272]

[EC 2.3.1.185 created 2008]