Biosynthesis of Grandione: An Example of Tandem Hetero Diels-Alder/Retro-Claisen Rearrangement Reaction?
Abstract
:1. Introduction
2. Results and Discussion
Tandem Reaction Analysis of Gradione
3. Materials and Methods
Computational Details
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available from the authors. |
Molecule | Exo | Endo | |||||||
---|---|---|---|---|---|---|---|---|---|
ΔGreac | ΔHreac | TΔSreac | ΔGact | ΔHact | TΔSact | ΔGact | ΔHact | TΔSact | |
Grandione | −19.07 | −36.31 | −17.24 | 37.31 | 20.85 | −16.45 | - | - | - |
Grandione β | −19.52 | −38.51 | −18.99 | 40.98 | 22.43 | −18.56 | 44.26 | 25.79 | −18.47 |
Isograndione | −20.29 | −38.54 | −18.24 | 37.74 | 22.13 | −15.61 | - | - | - |
Isograndione β | −20.26 | −38.84 | −18.58 | 43.94 | 25.95 | −17.99 | 33.43 | 15.80 | −17.63 |
Molecule | ΔGact(TS1) | ΔG(INT) | ΔGact(TS2) | ΔGreac |
---|---|---|---|---|
Grandione | 21.13 | 7.43 | 13.06 | −19.07 |
Isograndione | 27.00 | 8.27 | 15.06 | −20.29 |
Molecule | Exo | TS1 | ||
---|---|---|---|---|
∆Estr (ζ) | ∆Eint (ζ) | ∆Estr (ζ) | ∆Eint (ζ) | |
Grandione | 23.42 | −2.73 | 27.68 | −23.66 |
Isograndione | 23.90 | −1.84 | 35.61 | −27.66 |
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Quijano-Quiñones, R.F.; Castro-Segura, C.S.; Mena-Rejón, G.J.; Quesadas-Rojas, M.; Cáceres-Castillo, D. Biosynthesis of Grandione: An Example of Tandem Hetero Diels-Alder/Retro-Claisen Rearrangement Reaction? Molecules 2018, 23, 2505. https://doi.org/10.3390/molecules23102505
Quijano-Quiñones RF, Castro-Segura CS, Mena-Rejón GJ, Quesadas-Rojas M, Cáceres-Castillo D. Biosynthesis of Grandione: An Example of Tandem Hetero Diels-Alder/Retro-Claisen Rearrangement Reaction? Molecules. 2018; 23(10):2505. https://doi.org/10.3390/molecules23102505
Chicago/Turabian StyleQuijano-Quiñones, Ramiro F., Carolina S. Castro-Segura, Gonzalo J. Mena-Rejón, Mariana Quesadas-Rojas, and David Cáceres-Castillo. 2018. "Biosynthesis of Grandione: An Example of Tandem Hetero Diels-Alder/Retro-Claisen Rearrangement Reaction?" Molecules 23, no. 10: 2505. https://doi.org/10.3390/molecules23102505