Chapter9 - Chapter 9: Catalytic Strategies Lecture overview...

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1. Basic mechanisms of enzymatic catalysis More than the textbook! 1. Proteases: examples of enzymatic strategies 2. Applying enzymatic knowledge to drug-design 3. Carbonic Anhydrase - fast metal dependent enzyme 5. Restriction enzymes - sequence specific DNA cleavage 6. Nucleoside monophosphate kinases - induced fit forms active site Chapter 9: Catalytic Strategies Lecture overview Fritz Haber, 1909 Rhizobium, 3 Billion BC
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Reactivity of N N N N 942 kJ/mol Haber process Reduction of N 2 in the presence of H 2 gas over an iron catalyst 400 to 500 ° C ~200 atmospheres of pressure N 2 + 3 H 2 2 NH 3 Industrial Nitrification - The production of Ammonia Fritz Haber, 1909
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Biological nitrogen fixation
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Catalytic Principles: 1. Approximation (proximity) 2. General Acid/Base 3. Covalent attachment 5. Metal ions 4. Electrostatic
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Catalytic Principles: Proximity X Y O O O - O O O O + + - O k rel = 1 M -1 s -1 O O O O - k rel = 10 4 s -1 O O O + - O O O O O - k rel = 10 6 s -1 O O O + - O Tom Bruice, 1960 equivalent to 10 4 M!
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Catalytic Principles: Base catalysis R 1 C N O R 2 H O H H C N O R 2 H R 1 OH H + Uncatalyzed: Base catalyzed: R 1 C N O - R 2 H O H H + R 1 C N O R 2 H O H H - :B R 1 C N O - R 2 H O H HB C N O R 2 H R 1 OH H + - :B
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Catalytic Principles: Acid catalysis Uncatalyzed: Acid catalyzed: R 1 C N O R 2 H O H H AH C N O R 2 H R 1 OH H + AH R 1 C N O R 2 H R 1 C N O - R 2 H O H H O H H + C N O R 2 H R 1 OH H + R 1 C N OH R 2 H O H H + A -
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Catalytic Principles: Acid/Base tandem Pre-organized Acid and Base: R 1 O C R 2 H O R 1 O C R 2 O H H :B - A H :B - A H H R 1 O HC R 2 O H A: - B H v = k [acid] [base] [substrate] Separate Acid and Base: N H O α-πψριδονε Ν Ο Η ταυτομερ R 1 O C R 2 H O H R 1 O C R 2 H O H v = k' [ α -pyridone] [substrate] k' = k • 7000 M!
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Proteases Provides examples of covalent, electrostatic, and metal ion catalysis Cleave amide (peptide) bonds
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How to watch hydrolysis in real time Early release of amino group… implies retention of carboxylate
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How does Ser (pK a ~14) act as a nucleophile at pH~7? Similar studies identified an activated Histidine…
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Chapter9 - Chapter 9: Catalytic Strategies Lecture overview...

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