Regiospecific Hydrogenation of Bromochalcone by Unconventional Yeast Strains
Abstract
:1. Introduction
2. Results
3. Discussion
4. Materials and Methods
4.1. Substrates
4.2. Microorganisms
4.3. Screening
4.4. Gas Chromatography
4.5. Preparative Scale
4.6. TLC and NMR Analysis
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Strain | Substrate | Degree of Conversion after a Specified Incubation Time | |||
---|---|---|---|---|---|
1 Day | 3 Days | 7 Days | 10 Days | ||
Rhodotorula rubra KCh 4 | 1 | 7 | 22 | 71 | 75 |
2 | 10 | 13 | 14 | 21 | |
3 | 34 | 83 | 99 | >99 | |
4 | 67 | 87 | 90 | 92 | |
Rhodotorula rubra KCh 82 | 1 | 16 | 24 | 72 | 82 |
2 | 10 | 12 | 21 | 54 | |
3 | 34 | 68 | 99 | >99 | |
4 | 66 | 87 | 88 | 91 | |
Rhodotorula marina KCh 77 | 1 | 3 | 11 | 63 | 72 |
2 | 53 | 72 | 90 | 97 | |
3 | 23 | 47 | 92 | 99 | |
4 | 57 | 81 | 86 | 90 | |
Rhodotorula glutinis KCh 242 | 1 | 59 | 93 | 97 | 98 |
2 | 93 | 95 | 98 | 99 | |
3 | 15 | 38 | 67 | 89 | |
4 | 4 | 9 | 11 | 15 | |
Saccharomyces cerevisiae KCh 464 | 1 | 77 | 82 | 98 | 99 |
2 | 2 | 3 | 3 | 4 | |
3 | >99 | >99 | >99 | >99 | |
4 | 63 | 77 | 84 | 92 | |
Candida viswanathii KCh 120 | 1 | 94 | 96 | 98 | 99 |
2 | 32 | 52 | 94 | 96 | |
3 | 98 | 99 | >99 | >99 | |
4 | 6 | 30 | 34 | 75 | |
Candida parapsilosis KCh 909 | 1 | 92 | 95 | 97 | 98 |
2 | 80 | 85 | 94 | 95 | |
3 | 46 | 92 | >99 | >99 | |
4 | 3 | 15 | 18 | 20 | |
Yarrowia lipolytica KCh 71 | 1 | 98 | 99 | >99 | >99 |
2 | 90 | 95 | 97 | 98 | |
3 | 74 | 95 | 98 | 92 | |
4 | 91 | 93 | 95 | 96 |
Strain | Substrate | Degree of Conversion after Specified Incubation Time | |||
---|---|---|---|---|---|
1 h | 3 h | 6 h | 12 h | ||
Rhodotorula rubra KCh 4 | 4 | 31 | 38 | 45 | 50 |
Rhodotorula glutinis KCh 242 | 2 | 21 | 25 | 28 | 31 |
Saccharomyces cerevisiae KCh 464 | 1 | 31 | 40 | 56 | 71 |
3 | 58 | 81 | 94 | 99 | |
4 | 26 | 44 | 57 | 78 | |
Candida viswanathii KCh 120 | 1 | 81 | 99 | >99 | >99 |
3 | 23 | 40 | 68 | 94 | |
Candida parapsilosis KCh 909 | 1 | 75 | 92 | 94 | 96 |
2 | 29 | 58 | 82 | 88 | |
Yarrowia lipolytica KCh 71 | 1 | 96 | 98 | 98 | 99 |
2 | 91 | 95 | 96 | 97 | |
3 | 10 | 18 | 28 | 42 | |
4 | 80 | 93 | 96 | 97 |
Proton | Compound | |
---|---|---|
1 | 5 | |
H-2 | 8.26 (d, 1H, J = 15.4 Hz) | 3.30–3.36 (m, 2 H) |
H-3 | 7.59 (d, 1 H, J = 15.5 Hz) | 3.14–3.20 (m, 2 H) |
H-3′ | 7.04 (dd, 1 H, J = 8.4, 0.9 Hz) | 6.98 (dd, 1 H, J = 8.4, 1.2, 0.4 Hz) |
H-4′ | 7.52 (ddd, 1 H, J = 8.2, 7.2, 1.4 Hz) | 7.45 (ddd, 1 H, J = 8.4, 7.1, 1.6 Hz) |
H-5′ | 6.95 (ddd, 1 H, J = 8.1, 7.1, 1.0 Hz) | 6.87 (ddd, 1 H, J = 8.2, 7.1, 1.1 Hz) |
H-6′ | 7.91 (dd, 1 H, J = 8.1, 1.4 Hz) | 7.76 (dd, 1 H, J = 8.1, 1.6 Hz) |
H-3″ | 7.75 (dd, 1 H, J = 7.8, 1.4 Hz) | 7.55 (dd, 1 H, J = 8.0, 1.2 Hz) |
H-4″ | 7.38 (t, 1 H, J = 7.5 Hz) | 7.24 (td, 1 H, J = 7.4, 1.3 Hz) |
H-5″ | 7.28 (td, 1 H, J = 7.9, 1.6 Hz) | 7.09 (ddd, 1 H, J = 7.9, 7.3, 1.9 Hz) |
H-6″ | 7.66 (dd, 1 H, J = 8.0, 1.0 Hz) | 7.30 (dd, 1 H, J = 8.0, 1.2 Hz) |
-OH | 12.71 (s, 1 H) | 12.28 (s, 1 H) |
Carbon | Compound | |||||||
---|---|---|---|---|---|---|---|---|
1 | 5 | 2 | 6 | 3 | 7 | 4 | 8 | |
C-1 | 193.59 | 205.21 | 193.49 | 204.86 | 193.59 | 205.03 | 192.87 | 205.69 |
C-2 | 143.86 | 38.36 | 143.70 | 39.75 | 144.12 | 39.82 | 139.10 | 40.23 |
C-3 | 123.14 | 30.82 | 121.60 | 29.57 | 120.82 | 29.44 | 146.72 | 29.81 |
C-1′ | 120.03 | 119.37 | 120.02 | 119.30 | 120.05 | 119.34 | 121.39 | 120.60 |
C-2′ | 163.79 | 162.55 | 163,79 | 162.56 | 163.77 | 162.59 | 162.64 | 161.42 |
C-3′ | 118.85 | 118.65 | 118.85 | 118.74 | 118.84 | 118.77 | 128.80 | 120.71 |
C-4′ | 136.75 | 136.52 | 136.80 | 136.60 | 136.71 | 136.62 | 119.55 | 139.08 |
C-5′ | 119.06 | 119.08 | 119.10 | 119.12 | 119.05 | 119.12 | 110.59 | 110.61 |
C-6′ | 129.89 | 130.01 | 129.82 | 129.85 | 129.75 | 129.86 | 131.98 | 132.19 |
C-1″ | 134.90 | 140.11 | 136.84 | 143.21 | 133.64 | 139.83 | 134.44 | 140.50 |
C-2″ | 126.28 | 124.46 | 131.09 | 127.27 | 132.45 | 131.47 | 129.01 | 128.52 |
C-3″ | 128.15 | 133.07 | 123.31 | 122.72 | 130.10 | 130.34 | 129.25 | 128.78 |
C-4″ | 127.90 | 127.83 | 127.63 | 129.58 | 125.40 | 120.24 | 131.43 | 126.56 |
C-5″ | 131.80 | 128.30 | 130.86 | 130.28 | 140.10 | 130.34 | 129.25 | 128.78 |
C-6″ | 133.83 | 130.88 | 133.74 | 131.61 | 132.45 | 131.47 | 129.01 | 128.52 |
Proton | Compound | |
---|---|---|
2 | 6 | |
H-2 | 7.79–7.85 (m, 1 H) | 3.29–3.35 (m, 2 H) |
H-3 | 7.64 (d, 1 H, J = 15.5 Hz) | 3.00–3.08 (m, 2 H) |
H-3′ | 7.04 (d, 1 H, J = 8.1 Hz) | 6.99 (ddd, 1 H, J = 8.4, 1.1, 0.4 Hz) |
H-4′ | 7.52 (t, 1 H, J = 7.1) | 7.48 (ddd,1 H, J = 8.4, 7.2, 1.7 Hz) |
H-5′ | 6.96 (t, 1 H, J = 7.2 Hz) | 6.89 (dd, 1 H, J = 8.2, 7.1, 1.1. Hz) |
H-6′ | 7.92 (d, 1 H, J = 7.1 Hz) | 7.74 (dd, 1 H, J = 8.1, 1.6 Hz) |
H-2″ | 7.79–7.85 (m, 1 H) | 7.14–7.20 (m, 1 H) |
H-4″ | 7.54–7.58 (m, 1 H) | 7.33–7.37 (m, 1 H) |
H-5″ | 7.04 (d, 1 H, J = 8.1 Hz) | 7.14–7.20 (m, 1 H) |
H-6″ | 7.54–7.58 (m, 1 H) | 7.41–7.42 (m, 1 H) |
-OH | 12.70 (s, 1 H) | 12.23 (s, 1 H) |
Proton | Compound | |
---|---|---|
3 | 7 | |
H-2 | 7.84 (d, 1 H, J = 15.5 Hz) | 3.28–3.34 (m, 2 H) |
H-3 | 7.64 (d, 1 H, J = 5.5 Hz) | 3.00–3.06 (m, 2 H) |
H-3′ | 7.03 (dd, 1 H, J = 8.3, 0.8 Hz) | 6.99 (dd, 1 H, J = 8.3, 1.1 Hz) |
H-4′ | 7.49–7.53 (m, 1 H) | 7.47 (dddd, 1 H, J = 8.6, 7.0,1.7, 0.4 Hz) |
H-5′ | 6.95 (ddd, 1 H, J = 8.1, 7.1, 1.0 Hz) | 6.87 (ddd, 1 H, J = 8.2, 7.1, 1.1 Hz) |
H-6′ | 7.90 (dd, 1 H, J = 8.1, 1.4 Hz) | 7.73 (dd, 1 H, J = 8.1, 1.5 Hz) |
H-2″ | 7.56–7.59 (m, 1 H) | 7.40–7.44 (m, 1 H) |
H-3″ | 7.49–7.53 (m, 1 H) | 7.11–7.15 (m, 1 H) |
H-5″ | 7.49–7.53 (m, 1 H) | 7.11–7.15 (m, 1 H) |
H-6″ | 7.56–7.59 (m, 1 H) | 7.40–7.44 (m, 1 H) |
-OH | 12.74 (s, 1 H) | 12.23 (s, 1 H) |
Proton | Compound | |
---|---|---|
4 | 8 | |
H-2 | 7.56 (d, 1 H, J = 15.5 Hz) | 3.26–3.32 (m, 2 H) |
H-3 | 7.95 (d, 1 H, J = 15.4 Hz) | 3.02–3.09 (m, 2 H) |
H-3′ | 6.94 (d, 1 H, J = 8.9 Hz) | 6.88 (d, 1 H, J = 8.9 Hz) |
H-4′ | 7.57 (dd, 1 H, J = 8.0, 2.3 Hz) | 7.52 (dd, 1 H, J = 8.9,2.4 Hz) |
H-6′ | 8.01 (d, 1 H, J = 2.3 Hz) | 7.82 (d, 1 H, J = 2.4 Hz) |
H-2″ | 7.67–7.70 (m, 1 H) | 7.20–7.26 (m, 1 H) |
H-3″ | 7.43–7.48 (m, 1 H) | 7.29–7.34 (m, 1 H) |
H-4″ | 7.43–7.48 (m, 1 H) | 7.20–7.26 (m, 1 H) |
H-5″ | 7.43–7.48 (m, 1 H) | 7.29–7.34 (m, 1 H) |
H-6″ | 7.67–7.70 (m, 1 H) | 7.20–7.26 (m, 1 H) |
-OH | 12.74 (s, 1 H) | 12.19 (s, 1 H) |
Retention Times of Substrates (1–4) and Products (5–8) [min] | |||||||
---|---|---|---|---|---|---|---|
1 | 5 | 2 | 6 | 3 | 7 | 4 | 8 |
12.26 | 11.27 | 12.42 | 11.53 | 12.54 | 11.65 | 12.09 | 11.06 |
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Łużny, M.; Kaczanowska, D.; Gawdzik, B.; Wzorek, A.; Pawlak, A.; Obmińska-Mrukowicz, B.; Dymarska, M.; Kozłowska, E.; Kostrzewa-Susłow, E.; Janeczko, T. Regiospecific Hydrogenation of Bromochalcone by Unconventional Yeast Strains. Molecules 2022, 27, 3681. https://doi.org/10.3390/molecules27123681
Łużny M, Kaczanowska D, Gawdzik B, Wzorek A, Pawlak A, Obmińska-Mrukowicz B, Dymarska M, Kozłowska E, Kostrzewa-Susłow E, Janeczko T. Regiospecific Hydrogenation of Bromochalcone by Unconventional Yeast Strains. Molecules. 2022; 27(12):3681. https://doi.org/10.3390/molecules27123681
Chicago/Turabian StyleŁużny, Mateusz, Dagmara Kaczanowska, Barbara Gawdzik, Alicja Wzorek, Aleksandra Pawlak, Bożena Obmińska-Mrukowicz, Monika Dymarska, Ewa Kozłowska, Edyta Kostrzewa-Susłow, and Tomasz Janeczko. 2022. "Regiospecific Hydrogenation of Bromochalcone by Unconventional Yeast Strains" Molecules 27, no. 12: 3681. https://doi.org/10.3390/molecules27123681