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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.
Expert Solution
Step 1 Introduction

Whenever a reaction takes place there are reactants and they form products but in between, during the process of formation of product, we get an intermediate substance which is known as a transition substance. The stage where this substance is formed is the transition stage. As the name suggests, the transition state is the stage between the reactant and the product. It is mid-way between the two and at this time the reaction can either fall back to be a reactant or move forward to products. This is also called an activated complex. The name, "activated complex" is a mixture of reactant and product. 

Reactant + enzyme →  Reactant-enzyme complex→  Product + enzyme

                                          (transition state)

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