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Chemistry 30A3 Fall 2011 Labs Dr. Troendle 59

Chemistry 30A3 Fall 2011 Labs Dr. Troendle 59 - (b Can you...

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Chemical Biology 3OA3, September 2009 Page 59 2. (a) Which is the overall preferred hydrolysis site? (b) Are there any exceptions? 3. (a) Create a "box model" of OPE's active site based on the results in Table 4. Indicate the relative sizes of the hydrophobic sites, and rationalize your model. (b) Do the aromatic ring, R 3 and R 4 interact favourably / unfavourably / not at all with OPE? (c) Did the electron withdrawing character of R 3 = CH 2 CF 3 affect the rates relative to Et? (d) What effect would you expect an electron-withdrawing R 3 group to have on the reaction rate if the reaction occurred at R 3 ? 4. (a) Are there any exceptions to the generalizations made above?
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Unformatted text preview: (b) Can you rationalize these exceptions? 9. R EFERENCES 1. Koeller, K. M., and Wong, C.-H. (2000) Synthesis of Complex Carbohydrates and Glycoconjugates: Enzyme-Based and Programmable One-Pot Strategies, Chemical Reviews (Washington, D. C.) 100 , 4465-4493. 2. Wong, C. H., and Whitesides, G. M. (1994) Enzymes in synthetic organic chemistry , Pergamon, Oxford. 3. Jones, J. B. (1993) Probing the specificity of synthetically useful enzymes, Aldrichimica Acta 26 , 105-112. 4. Jones, J. B., and Desantis, G. (1999) Toward understanding and tailoring the specificity of synthetically useful enzymes, Acc. Chem. Res. 32 , 99-107....
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