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Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric Hydrogenation Chen, Q.-A.; Gao, K.; Duan, Y.; Ye, Z.-S.; Shi, L.; Yang, Y.; Zhou, Y.-G. J. Am. Chem. Soc. 2012, 134, 2442-2448 October 16, 2012
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Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric Hydrogenation Chen, Q.-A.; Gao, K.; Duan, Y.; Ye, Z.-S.; Shi, L.; Yang, Y.; Zhou, Y.-G. J. Am. Chem. Soc. 2012, 134, 2442-2448 October 16, 2012
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3 Background: NADH and NADPH in Living Cells Coenzyme found in living cells. NADPH: anabolic pathways such as lipid synthesis, cholesterol synthesis and fatty acid chain elongation. (Reductive biosynthesis) NADH: coenzyme for oxidoreductases; citric acid cycle; catabolism; fatty acid oxidation; glycolysis (geneation of ATP)
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4 Background: NADH and NADPH in Living Cells Anaerobic Conditions
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5 Glyceraldehyde-3-phosphate Dehydrogenase
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6 Fatty Acid Biosynthesis How good hydride donors are NADH and NADPH?
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7 Relative Hydride Donor Ability of HEH Mayr, H.; Bug, T.; Gotta, M. F.; Hering, N.; Irrgang, B.; Janker, B.; Kempf, B.; Loos, R.; Ofial, A. R.; Remennikov, G.; Schimmel, H. J. Am. Chem. Soc. 2001, 123, 9500.
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8 Relative Hydride Donor Ability of HEH Richter, D.; Mayr, H. Angew. Chem. Int. Ed. 2009, 48, 1958.
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9 Relative Hydride Donor Ability of HEH
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10 Background: HEH As an Organic Reagent Mayer, S.; List, B. Angew. Chem. Int. Ed. 2006, 45, 4193.
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11 Background: HEH As an Organic Reagent Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem. Int. Ed. 2006, 45, 6751.
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12 Background: HEH as an Organic Catalyst Will reduce pyridine without reducing the imine Regioselectivity of the reduction
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13 Background: HEH as an Organic Catalyst Chen, Q. A.; Chen, M. W.; Yu, C. B.; Shi, L.; Wang, D. S.; Yang, Y.; Zhou, Y. G. J. Am. Chem. Soc. 2011, 133, 16432.
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14 Background: HEH as an Organic Catalyst Chen, Q. A.; Chen, M. W.; Yu, C. B.; Shi, L.; Wang, D. S.; Yang, Y.; Zhou, Y. G. J. Am. Chem. Soc. 2011, 133, 16432.
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15 Background: HEH as an Organic Catalyst Chen, Q. A.; Chen, M. W.; Yu, C. B.; Shi, L.; Wang, D. S.; Yang, Y.; Zhou, Y. G. J. Am. Chem. Soc. 2011, 133, 16432.
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16 Background: HEH as an Organic Catalyst Harsh conditions for the regeneration of HEH limit the substrate scope: limited to benzoxazinones Search for New NAD(P)H Analogs
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17 Their Inspiration Chen, Q. A.; Wang, D. S.; Zhou, Y. G.; Duan, Y.; Fan, H. J.; Yang, Y.; Zhang, Z. J. Am. Chem. Soc. 2011, 133, 6126.
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18 Background: New NAD(P)H Analog
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19 Development of New NAD(P)H Mimics: Ease of Phenanthridine Reduction
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20 Development of New Regenerable NAD(P)H Mimics
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21 Reaction Scope
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22 Reaction Scope
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23 Reaction Scope
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24 Reaction Scope
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25 Postulated Mechanism
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