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QUESTION: For each enzyme identify the transition-state inhibitor analog by drawing a circle around it and give a brief explanation of why it mimics the structure of the transition- state species.

QUESTION: For each enzyme identify the transition-state inhibitor analog by drawing a circle around it and give a brief explanation of why it mimics the structure of the transition- state species.

Biochemistry
Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
Problem 1P
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Enzyme Carboxypeptidase A CBZ-NH-CH, C-NH-CH-COOH CH₂ C6H5 Papain a-chymotrypsin Substrate HIV protease N-CBZ-glycyl-L-phenylalanine ก CBZ-NHCH--C--NH-CH, CẢNH CH2 CH₂ N-CBZ-L-phenylalanyl-glycyl- p-nitroanilide CHỦ NHCH I CH2 CH --NH-CH-C-NH--CH,-COOH N-acetyl-L-phenylalanyl-glycine NH on C.NH NO₂ CH3 CH₂ CH2 C6H5 -NH-CH--COOH 1 CH3 N-acetyl-L-valyl-L-phenylalanyl-L-alanine Inhibitor I i CBZ-NH-CH -C--NH-CH-COOH 3Z--NH-CH I CH 3 CH2 C Hs N-CBZ-D-alanyl-L-phenylalanine CBZ--NH-CH--C--NH--CH, I CH₂ C6H5 N-CBZ-L-phenylalanyl-glycinal CH3-C-NH-CH-C-OH CH₂ C6H5 N-acetyl-L-phenylalanine CH3 quemq CH₂-CH-COOH -NH-CH-C-CH2-CH-COOH CH2 CH3 CH3 CH3 C6H5 --NH-- N-(N-(acetyl)-valyl)-5-amino-5-benzyl-4-keto- 2-methyl-pentanoic acid Inhibitor II CBZ-NH-CH₂--P--NH--CH--COOH 0 N-(CBZ-aminomethyl-oxyhydroxyphos- phinyl)-L-phenylalanine 1 CH2 C6H5 CBZ--NH-CH--C--NH-CH2-COOH I CH 2 C6H5 i N-CBZ-L-phenylalanyl-glycine CH3--C--NH--CH--CH(OH)CH₂CH2COOH CH2 C6H5 N-acetyl-5-amino-5-benzyl-4-hydroxy- pentanoic acid 요 i CHy-C-NH-CH-C-NH-CH --OH CH2 CH3 CH3 C6H5 N-acetyl-L-valyl-L-phenylalanine The diagram above compares for each of four different proteolytic enzymes the chemical bonding structure of a classical substrate with the structures of two competitive in-hibitors. For each substrate structure, an arrow indicates the position of the scissile bond that is cleaved by enzyme action and a green circle identifies the part of the substrate for specific-ity of substrate recognition. For each enzyme, one of the inhibitors is a classical competitive inhibitor while the other is a transition-state inhibitor analog. QUESTION: For each enzyme identify the transition-state inhibitor analog by drawing a circle around it and give a brief explanation of why it mimics the structure of the transition- state species.
Transcribed Image Text:Enzyme Carboxypeptidase A CBZ-NH-CH, C-NH-CH-COOH CH₂ C6H5 Papain a-chymotrypsin Substrate HIV protease N-CBZ-glycyl-L-phenylalanine ก CBZ-NHCH--C--NH-CH, CẢNH CH2 CH₂ N-CBZ-L-phenylalanyl-glycyl- p-nitroanilide CHỦ NHCH I CH2 CH --NH-CH-C-NH--CH,-COOH N-acetyl-L-phenylalanyl-glycine NH on C.NH NO₂ CH3 CH₂ CH2 C6H5 -NH-CH--COOH 1 CH3 N-acetyl-L-valyl-L-phenylalanyl-L-alanine Inhibitor I i CBZ-NH-CH -C--NH-CH-COOH 3Z--NH-CH I CH 3 CH2 C Hs N-CBZ-D-alanyl-L-phenylalanine CBZ--NH-CH--C--NH--CH, I CH₂ C6H5 N-CBZ-L-phenylalanyl-glycinal CH3-C-NH-CH-C-OH CH₂ C6H5 N-acetyl-L-phenylalanine CH3 quemq CH₂-CH-COOH -NH-CH-C-CH2-CH-COOH CH2 CH3 CH3 CH3 C6H5 --NH-- N-(N-(acetyl)-valyl)-5-amino-5-benzyl-4-keto- 2-methyl-pentanoic acid Inhibitor II CBZ-NH-CH₂--P--NH--CH--COOH 0 N-(CBZ-aminomethyl-oxyhydroxyphos- phinyl)-L-phenylalanine 1 CH2 C6H5 CBZ--NH-CH--C--NH-CH2-COOH I CH 2 C6H5 i N-CBZ-L-phenylalanyl-glycine CH3--C--NH--CH--CH(OH)CH₂CH2COOH CH2 C6H5 N-acetyl-5-amino-5-benzyl-4-hydroxy- pentanoic acid 요 i CHy-C-NH-CH-C-NH-CH --OH CH2 CH3 CH3 C6H5 N-acetyl-L-valyl-L-phenylalanine The diagram above compares for each of four different proteolytic enzymes the chemical bonding structure of a classical substrate with the structures of two competitive in-hibitors. For each substrate structure, an arrow indicates the position of the scissile bond that is cleaved by enzyme action and a green circle identifies the part of the substrate for specific-ity of substrate recognition. For each enzyme, one of the inhibitors is a classical competitive inhibitor while the other is a transition-state inhibitor analog. QUESTION: For each enzyme identify the transition-state inhibitor analog by drawing a circle around it and give a brief explanation of why it mimics the structure of the transition- state species.
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