Pseudotropine acyltransferase

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Pseudotropine acyltransferase
Identifiers
EC no. 2.3.1.186
CAS no. 162535-26-4&title= 138440-78-5, 162535-26-4
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Pseudotropine acyltransferase (EC 2.3.1.186, pseudotropine:acyl-CoA transferase, tigloyl-CoA:pseudotropine acyltransferase, acetyl-CoA:pseudotropine acyltransferase, pseudotropine acetyltransferase, pseudotropine tigloyltransferase, PAT) is an enzyme with systematic name acyl-CoA:pseudotropine O-acyltransferase. [1] [2] [3] [4] This enzyme catalyses the following chemical reaction

acyl-CoA + pseudotropine CoA + O-acylpseudotropine

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

Related Research Articles

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Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Its corresponding conjugate acid at pH 7.3 major species is known as tropiniumone.

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<span class="mw-page-title-main">Homocitrate synthase</span> Enzyme

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<span class="mw-page-title-main">Loline alkaloid</span> Class of chemical compounds

A loline alkaloid is a member of the 1-aminopyrrolizidines, which are bioactive natural products with several distinct biological and chemical features. The lolines are insecticidal and insect-deterrent compounds that are produced in grasses infected by endophytic fungal symbionts of the genus Epichloë. Lolines increase resistance of endophyte-infected grasses to insect herbivores, and may also protect the infected plants from environmental stresses such as drought and spatial competition. They are alkaloids, organic compounds containing basic nitrogen atoms. The basic chemical structure of the lolines comprises a saturated pyrrolizidine ring, a primary amine at the C-1 carbon, and an internal ether bridge—a hallmark feature of the lolines, which is uncommon in organic compounds—joining two distant ring carbons. Different substituents at the C-1 amine, such as methyl, formyl, and acetyl groups, yield loline species that have variable bioactivity against insects. Besides endophyte–grass symbionts, loline alkaloids have also been identified in some other plant species; namely, Adenocarpus species and Argyreia mollis.

<span class="mw-page-title-main">Biosynthesis of cocaine</span>

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<span class="mw-page-title-main">Littorine</span> Chemical compound

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References

  1. Rabot S, Peerless AC, Robins RJ (1995). "Tigloyl-CoA:pseudotropine acyltransferase an enzyme of tropane alkaloid biosynthesis". Phytochemistry. 39 (2): 315–322. doi:10.1016/0031-9422(94)00907-b.
  2. Robins RJ, Bachmann P, Robinson T, Rhodes MJ, Yamada Y (November 1991). "The formation of 3 alpha- and 3 beta-acetoxytropanes by Datura stramonium transformed root cultures involves two acetyl-CoA-dependent acyltransferases". FEBS Letters. 292 (1–2): 293–7. doi: 10.1016/0014-5793(91)80887-9 . PMID   1959620.
  3. Robins RJ, Bachmann P, Peerless AC (1994). "Esterification reactions in the biosynthesis of tropane alkaloids in transformed root cultures". Plant Cell Tissue Organ Cult. 38 (2–3): 241–247. doi:10.1007/bf00033883. S2CID   21524758.
  4. Boswell HD, Dräger B, McLauchlan WR, Portsteffen A, Robins DJ, Robins RJ, Walton NJ (November 1999). "Specificities of the enzymes of N-alkyltropane biosynthesis in Brugmansia and Datura". Phytochemistry. 52 (5): 871–8. doi:10.1016/S0031-9422(99)00293-9. PMID   10626376.