Ch1b09Lecture22

Ch1b09Lecture22 - 1 L e c tu r e 2 2 M a r c h 2 2 0 0 9 S...

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Lecture 22 - March 2, 2009 Summary of last lecture •displacement reaction and optical activity •reaction mechanisms and drug design Preview of coming attractions •drug design and HIV protease •intermolecular forces 1
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http://en.wikipedia.org/wiki/Image:HIV_Viron.png http://www.niaid.nih.gov/factsheets/howhiv.htm structural organization of the human immunodeficiency virus (HIV) p17 p24 p66 2
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p32 p66 p11 p55 outside inside inside p15 capsid matrix p24 p7 p6 p17 gag p55 p160 gagpol gag + protease + RT + integrase env gp120 gp45 polyprotein processing in the HIV life cycle HIV protease cleaves gag/gagpol http://en.wikipedia.org/wiki/Image:HIV_genome.png genomic organization of HIV 3
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http://en.wikipedia.org/wiki/File:Activation2_updated.svg Pauling: Enzymes and other catalysts accelerate the rates of reaction by being complementary to the transition state of a reaction and lowering the activation E stable compounds that resemble the transition state should bind more tightly to an enzyme than substrates and are therefore inhibitors (and drugs) 4
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peptide bond formation/hydrolysis enzyme catalyzed hydrolysis of peptide bonds: a displacement reaction (enzymes are protein catalysts) 5 R CO 2 H + NH 2 R' R C O N R' H + H 2 O O R N H R' C O - R N H R' C HO O R OH H 2 N C R' Transition State (tetrahedral intermediate) sp 3 sp 2 + + H-B' :B' + H-B' HO sp 2 B: H BH + BH + B, B' = bases (amino acid side chains of the enzyme catalyst)
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the “arrow” notation (Parsons section 4.1) The curved arrows represent movement of electron pairs being made and being broken. The arrow begins with the pair of electrons that will form the
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Ch1b09Lecture22 - 1 L e c tu r e 2 2 M a r c h 2 2 0 0 9 S...

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