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1. Introduction
2. Organic chemistry vs. biochemistry
3. Conversion of lanosterole to cholesterol
4. Biomimetic chemistry 1
5. Biomimetic chemistry 2
6. Selective remote functionalization of a steroid
7. Radical relay chlorination
8. A pyridine ring template
9. Why is this not enough?
10. Characteristic properties of cytochromes P-450
11. Mimics of cytochrome P-450
12. Side view of the porphyrin system
13. Making a di-ester from a steroid
14. A catalyst with fluorinated phenyl rings
15. Making the catalyst
16. A catalyst with an attached pyridine ring
17. A precursor of the pyridine catalyst
18. A molecular model of the system
19. Steroid models
20. Molecular model of the triple-ester steroid
21. An idealization (JOC cover)
22. Binding of lithocholic acid to beta-cyclodextrin
23. Ignoring the double bond
24. Ignoring functional groups?
25. Enzymes are large molecules
26. Polymer-based enzyme mimics
27. Synthesis of our transaminase mimic
28. Our pyridoxamine/polymer hybrid
29. Transamination with acid/base catalysis
30. Polyethylenimine has N: bases and N-H+ acids
31. Rate acceleration per pyridoxamine
32. Rate enhancement over pyridoxamine w/ pyruvate
33. Kinetic saturation indicates substrate binding
34. Michaelis-Menten kinetics 1
35. Michaelis-Menten kinetics 2
36. Why binding?
37. More hydrophobic substrates give stronger binding
38. C-12 hybrid selectivity for a hydrophobic substrate
39. Reversible binding of a pyridoxamine "Coenzyme"
40. Free pyridoxamine binding to the polymer
41. Hydrophobic substrates show larger accelerations
42. Pyridoxal to Pyridoxamine 1
43. Pyridoxal to Pyridoxamine 2
44. The catalytic cycle
45. Acknowledgements

Topics Covered

• Biomimetic catalysis
• Imitating enzymes for improved chemistry
• Using geometric control in a catalyst-substrate complex
• Mimics of cytochrome P-450, and of transaminase enzymes
• High rate accelerations and high selectivities

Links

Series:

• Chemical Biology

Categories:

• Biochemistry

Talk Citation

Publication History

• Published on August 14, 2008

Financial Disclosures

• Prof. Ronald Breslow has not informed HSTalks of any commercial/financial relationship that it is appropriate to disclose.