Lactones 41. Synthesis and Microbial Hydroxylation of Unsaturated Terpenoid Lactones with p-Menthane Ring Systems †
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Odoriferous Properties of Racemic [(±)-2] and Optically Active [(–)-(1R,6R)-2 and (+)-(1S,6S)-2]δ,ε-Unsaturated Lactones
Compound | Odour description |
---|---|
(±)- 2 | Weak, slightly similar to (+)- 2 |
(–)-(1 R,6R)-2 | Intensive, dill |
(+)-(1 S,6S)-2 | Medium intensity, coumarin-like |
2.2. Biotransformation of Racemic δ,ε-Unsaturated Lactone [(±)-2]
Microorganism | Time (days) | 2 | 3 | 4 * | ||||||
---|---|---|---|---|---|---|---|---|---|---|
(%) | ee (%) | Config. | (%) | ee (%) | ** | Config. | (%) | ** | ||
A. cylindrospora AM336 | 1 | 66 | 3 | (1S,6S) | 14 | 14 | (1S,3S,6S) | 20 | ||
2 | 41 | 0 | - | 22 | 36 | (1S,3S,6S) | 37 | |||
4 | 0 | - | - | 39 | 39 | +8.3 (c 0.38) | (1S,3S,6S) | 61 | +2.2 (c 0.23) | |
A. glauca AM177 | 2 | 67 | 7 | (1S,6S) | 6 | 0 | - | 27 | ||
4 | 32 | 6 | (1S,6S) | 15 | 20 | (1S,3S,6S) | 53 | |||
6 | 9 | 9 | (1S,6S) | 23 | 22 | +5.1 (c 0.10) | (1S,3S,6S) | 68 | +0.8 (c 1.28) | |
S. racemosum AM105 | 2 | 43 | 72 | (1S,6S) | 17 | 18 | (1S,3S,6S) | 40 | ||
4 | 11 | 54 | (1S,6S) | 20 | 35 | (1S,3S,6S) | 69 | |||
6 | 8 | 50 | (1S,6S) | 21 | 38 | +6.8 (c 0.36) | (1S,3S,6S) | 71 | +1.1 (c 1.19) |
3. Experimental
3.1. General
3.2. Chemical Synthesis
3.3. Microorganisms
3.4. Screening-Scale Biotransformations
3.5. Preparative-Scale Biotransformations
4. Conclusions
Supplementary Materials
Acknowledgments
References
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Grudniewska, A.; Wawrzeńczyk, C. Lactones 41. Synthesis and Microbial Hydroxylation of Unsaturated Terpenoid Lactones with p-Menthane Ring Systems. Molecules 2013, 18, 2778-2787. https://doi.org/10.3390/molecules18032778
Grudniewska A, Wawrzeńczyk C. Lactones 41. Synthesis and Microbial Hydroxylation of Unsaturated Terpenoid Lactones with p-Menthane Ring Systems. Molecules. 2013; 18(3):2778-2787. https://doi.org/10.3390/molecules18032778
Chicago/Turabian StyleGrudniewska, Aleksandra, and Czesław Wawrzeńczyk. 2013. "Lactones 41. Synthesis and Microbial Hydroxylation of Unsaturated Terpenoid Lactones with p-Menthane Ring Systems" Molecules 18, no. 3: 2778-2787. https://doi.org/10.3390/molecules18032778