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Molecules 2016, 21(11), 1551; doi:10.3390/molecules21111551

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

1
Facultad de Química, Universidad Autónoma de Yucatán, Calle 43 No. 613, Col. Inalambrica, Mérida, Yucatán, C.P. 97069, Mexico
2
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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Abstract

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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MDPI and ACS Style

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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