Quiz 7 - 2 Et N CO 2 Et O O CO 2 Et H 3 O OH H 3 N O CO 2 H...

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MCMP 205 Friday, April 24, 2009 20 pts Name __________________________ Lab TA _________________________ Lab Period ______________________ Quiz 7 1. (12 pts) Amino acid and peptide structure. a) Draw the structure of aspartic acid (D) in the form that would predominate in aqueous solution at pH 7. c) Outline a synthesis of aspartic acid using the starting materials shown below as well as any necessary reagents. Show the intermediate following each synthetic step. 1 OH H 2 N O G = OH H 2 N O R = N H NH 2 NH OH H 2 N O D = CO 2 H pKa1 = 2.34 pKa2 = 9.60 pKa1 = 2.17 pKa2 = 9.04 pKa3 = 12.48 pKa1 = 1.88 pKa2 = 3.65 pKa3 = 9.60 b) Draw the structure of the peptide RGD in the form that would predominate in solution at pH 7. OH H 2 N O CO 2 H from CO 2 Et N CO 2 Et O OEt Br O O H and O H 3 N O CO 2 2 pts N H H 3 N O NH NH 2 H 2 N H N O O O CO 2 3 pts correct amide backbone 1 pt 1 pt 1 pt 1 pt NaOEt EtOH CO 2 Et N CO 2 Et O O O OEt Br CO
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Unformatted text preview: 2 Et N CO 2 Et O O CO 2 Et H 3 O + OH H 3 N O CO 2 H 1 pt 1 pt 1 pt Name __________________________ 2. (4 pts) Draw the structure of the major product obtained from each of the following reactions. 3. (4 pts) Draw a Haworth projection for α-D-idopyranose. 2 OH H 2 N O N H N O O N O O HO N O O a) b) CHO CH 2 OH H HO OH H H HO OH H D-idose O H 2 N O solid phase OH H N O Fmoc Dicyclohexyl-carbodiimide (DCC) N-hydroxy-succinimide (NHS) H N H N O dicyclohexylurea pH 9 buffer (It is not necessary to know the structures of Fmoc, DCC or NHS to answer the question, but you do need to understand their roles) O OH OH OH OH OH 1 pt for alpha OH 1 pt for 6-membered ring 2 pts for correct placement of other OH groups and CH 2 OH N H N H N O O O N H O Fmoc O H N O solid phase...
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Quiz 7 - 2 Et N CO 2 Et O O CO 2 Et H 3 O OH H 3 N O CO 2 H...

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