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Molecules 2016, 21(11), 1551;

Biogenesis of Triterpene Dimers from Orthoquinones Related to Quinonemethides: Theoretical Study on the Reaction Mechanism

Facultad de Química, Universidad Autónoma de Yucatán, Calle 43 No. 613, Col. Inalambrica, Mérida, Yucatán, C.P. 97069, Mexico
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Ciudad de México, C.P. 04510, Mexico
Authors to whom correspondence should be addressed.
Academic Editor: James W. Gauld
Received: 10 October 2016 / Revised: 7 November 2016 / Accepted: 11 November 2016 / Published: 17 November 2016
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The biogenetic origin of triterpene dimers from the Celastraceae family has been proposed as assisted hetero-Diels-Alder reaction (HDA). In this work, computational calculation of HDA between natural quinonemethides (tingenone and isopristimerol) and hypothetical orthoquinones has been performed at the M06-2X/6-31G(d) level of theory. We have located all the HDA transition states supporting the biogenetic route via HDA cycloadditions. We found that all reactions take place through a concerted inverse electron demand and asynchronous mechanism. The enzymatic assistance for dimer formation was analyzed in terms of the calculated transition state energy barrier. View Full-Text
Keywords: Celastraceae; quinonemethide; biogenesis; hetero Diels-Alder; DFT Celastraceae; quinonemethide; biogenesis; hetero Diels-Alder; DFT

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Quesadas-Rojas, M.; Mena-Rejón, G.J.; Cáceres-Castillo, D.; Cuevas, G.; Quijano-Quiñones, R.F. Biogenesis of Triterpene Dimers from Orthoquinones Related to Quinonemethides: Theoretical Study on the Reaction Mechanism. Molecules 2016, 21, 1551.

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