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J. Am. Chem. Soc. 2012 , 134 , 2442-2448 October 16, 2012 PowerPoint Presentation
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J. Am. Chem. Soc. 2012 , 134 , 2442-2448 October 16, 2012

J. Am. Chem. Soc. 2012 , 134 , 2442-2448 October 16, 2012

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J. Am. Chem. Soc. 2012 , 134 , 2442-2448 October 16, 2012

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  1. J. Am. Chem. Soc. 2012, 134, 2442-2448 October 16, 2012 Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric HydrogenationChen, Q.-A.; Gao, K.; Duan, Y.; Ye, Z.-S.; Shi, L.; Yang, Y.; Zhou, Y.-G.

  2. J. Am. Chem. Soc. 2012, 134, 2442-2448 October 16, 2012 Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric HydrogenationChen, Q.-A.; Gao, K.; Duan, Y.; Ye, Z.-S.; Shi, L.; Yang, Y.; Zhou, Y.-G.

  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)

  4. Background: NADH and NADPH in Living Cells Anaerobic Conditions

  5. Glyceraldehyde-3-phosphate Dehydrogenase

  6. Fatty Acid Biosynthesis How good hydride donors are NADH and NADPH?

  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.

  8. Relative Hydride Donor Ability of HEH Richter, D.; Mayr, H.Angew. Chem. Int. Ed.2009, 48, 1958.

  9. Relative Hydride Donor Ability of HEH

  10. Background: HEH As an Organic Reagent Mayer, S.; List, B. Angew. Chem. Int. Ed.2006, 45, 4193.

  11. Background: HEH As an Organic Reagent Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem. Int. Ed.2006, 45, 6751.

  12. Background: HEH as an Organic Catalyst Will reduce pyridine without reducing the imine Regioselectivity of the reduction

  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.

  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.

  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.

  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

  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.

  18. Background: New NAD(P)H Analog

  19. Development of New NAD(P)H Mimics: Ease of Phenanthridine Reduction

  20. Development of New Regenerable NAD(P)H Mimics

  21. Reaction Scope

  22. Reaction Scope

  23. Reaction Scope

  24. Reaction Scope

  25. Postulated Mechanism