Monooxygenase- and Dioxygenase-Catalyzed Oxidative Dearomatization of Thiophenes by Sulfoxidation, cis-Dihydroxylation and Epoxidation
Abstract
:1. Introduction
2. Dioxygenase-Catalyzed Dearomatization of Thiophenes 1a–g
2.1. Enzymatic Oxidation of Thiophenes 1a–g to Yield cis-Dihydrodiols
2.2. Oxidations of Thiophenes 1a–g to Yield Sulfoxide Metabolites
2.3. Molecular Docking of Thiophenes 1a and 1g at the TDO Active Site
3. Dioxygenase-Catalyzed Dearomatization of 3-Substituted Thiophenes 1h–k
3.1. Oxidations of Thiophenes 1h–k to Yield cis-Dihydrodiol and Sulfoxide Metabolites
3.2. Molecular Docking of 3-Phenylthiophene 1k at the TDO Active Site
4. Dioxygenase-Catalyzed Dearomatization of Benzo[b]thiophenes 10a–d
4.1. Biotransformations of Benzo[b]thiophenes 10a–d to Yield cis-Dihydrodiols 11a–c
4.2. Biotransformations of Benzo[b]thiophenes 10a–d to Yield cis-Dihydrodiols 17a–d and trans-Dihydrodiols 19a, 19d
4.3. Biotransformations of Benzo[b]thiophenes 10a–d to Yield Sulfoxides 23a–d
5. Dioxygenase-Catalyzed Dearomatization of Tri- and Tetra-Cyclic Thiaarenes
5.1. Dioxygenase-Catalyzed Biotransformations of Dibenzo[b,d]thiophenes 33 and 38
5.2. Dioxygenase-Catalyzed Biotransformation of Benzo[b]naphtho[1,2-d]thiophene 30a and Tetrahydrobenzo[b]naphtho[1,2-d]thiophene 45
5.3. Dioxygenase-Catalyzed Biotransformation of Benzo[b]naphtho[2,1-d]thiophene 34
5.4. Application of Thiophene cis-Dihydrodiols in Thiophene Epoxide Synthesis
6. Monooxygenase-Catalyzed Sulfoxidation and Epoxidation of Thiophenes
6.1. CYP450-Catalyzed Sulfoxidation of Monocyclic Thiophenes
6.2. CYP450-Catalyzed Epoxidation of Monocyclic Thiophenes
6.3. Monooxygenase-Catalyzed Oxidation of Polycyclic Thiophenes
6.4. Monooxygenase-Catalyzed Thiophene Ring Oxidation of Thienopyridine Prodrugs
7. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Dedication
References
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Substrates 1a–g; Strain | 5a–g (%) | 6a–g (%) | 7a–g (%) | 2a–g/4a–g (%) | 8a–g (%) |
---|---|---|---|---|---|
1a, R = R′ = H (TDO) a | 0 | 79 | 21 | <1 (0.2) | 0 |
1b, R = Me, R′ = H (TDO) a | 0 | 25 | 75 | 0 | 0 |
1c, R = Et, R′ = H (TDO) a | 0 | 100 | 0 | 0 | 0 |
1d, R = Cl, R′ = H (TDO) a | 0 | 100 | 0 | 0 | 0 |
1e, R = Br, R′ = H (TDO) a | 0 | 100 | 0 | 0 | 0 |
1f, R = I, R′ = H (TDO) a | 0 | 100 | 0 | 0 | 0 |
1g, R = Ph, R′ = H (TDO) a | 0 | 67 | 6 | 0 | 27 |
1g, R = Ph, R′= H (TDO) b | 0 | 40 | 0 | 0 | 60 |
1g, R = Ph, R′ = H (NDO) c | 0 | 0 | 0 | 0 | 100 |
1g, R= Ph, R′ = H (NDO) d | 0 | 0 | 0 | 100 | 0 |
Substrates 1h–k; Strain | 5h–k (%) | 6h–k(%) | 7h–k (%) | 2h–k/4h–k (%) | 9k(%) |
---|---|---|---|---|---|
1h, R = H, R′ = Me (TDO) a | 0 | 0 | 24 | 76 | 0 |
1i, R = H, R′ = Cl (TDO) a | 0 | 59 | 0 | 41 | 0 |
1j, R = H, R′ = Br (TDO) a | 0 | 46 | 0 | 54 | 0 |
1k, R = H, R′ = Ph (TDO) a | 0 | 35 | 0 | 48 | 17 |
1k, R = H, R′ = Ph (NDO) b | 0 | 2 | 0 | 0 | 98 |
1k, R = H, R′ = Ph (NDO) c | 0 | 80 | 0 | 20 | 0 |
Substrates 10a–d (Dioxygenase) | 11a–c (%) | 17a–d (%) | 23a–c (%) |
---|---|---|---|
10a, R = R′ = R″ = H (TDO) a | 10 e | 63 | 12 i |
10a, R = R′ = R″ = H (NDO) b | 100 | ||
10a, R = R′ = R″ = H (NDO) c | 0 | 85 | 15 |
10a, R = R′ = R″ = H (NDO) d | 0 | 86 | 14 |
10b, R = Me, R′ = R″ = H (TDO) a | 83 | 10 f | 7 |
10b, R = Me, R′ = R″ = H (NDO) b | 0 | 0 g | 90 |
10b, R = Me, R′ = R″ = H (NDO) c | 90 | 0 | 10 |
10b, R = Me, R′ = R″ = H (NDO) d | 0 | 60 | 42 |
10c, R′ = Me, R = R″ = H (TDO) a | 100 | 0 | 0 |
10c, R′ = Me, R = R″ = H (NDO) b | 0 | 0 h | 42 |
10c, R′ = Me, R = R″ = H (NDO) c | 0 | 10 f | 90 |
10c, R′ = Me, R = R″ = H (NDO) d | 0 | 0 | 100 |
10d, R″ = Me, R = R′ = H (TDO) a | 0 | 100 | 0 |
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Boyd, D.R.; Sharma, N.D.; Stevenson, P.J.; Hoering, P.; Allen, C.C.R.; Dansette, P.M. Monooxygenase- and Dioxygenase-Catalyzed Oxidative Dearomatization of Thiophenes by Sulfoxidation, cis-Dihydroxylation and Epoxidation. Int. J. Mol. Sci. 2022, 23, 909. https://doi.org/10.3390/ijms23020909
Boyd DR, Sharma ND, Stevenson PJ, Hoering P, Allen CCR, Dansette PM. Monooxygenase- and Dioxygenase-Catalyzed Oxidative Dearomatization of Thiophenes by Sulfoxidation, cis-Dihydroxylation and Epoxidation. International Journal of Molecular Sciences. 2022; 23(2):909. https://doi.org/10.3390/ijms23020909
Chicago/Turabian StyleBoyd, Derek R., Narain D. Sharma, Paul J. Stevenson, Patrick Hoering, Christopher C. R. Allen, and Patrick M. Dansette. 2022. "Monooxygenase- and Dioxygenase-Catalyzed Oxidative Dearomatization of Thiophenes by Sulfoxidation, cis-Dihydroxylation and Epoxidation" International Journal of Molecular Sciences 23, no. 2: 909. https://doi.org/10.3390/ijms23020909