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Chapter 11: Q17P (page 359)

Design a chloromethylketone inhibitor of elastase.

Short Answer

Expert verified

Tosyl-L-alanine chloromethylkeyone

Step by step solution

01

Inhibitor of digestive enzyme

Inhibitors of digestive enzymes inhibit the functional enzymes that switch off the functionality and activity of different digestive enzymes; for example, they inhibit trypsin and elastase.

02

Chloromethyl ketone inhibitor

One of the inhibitors of elastase is chloromethyl ketone inhibitor because it is a strong alkylating agent; it reacts only with His 57, thereby inactivating the enzyme elastase, which is designed as follows:

Tosyl-L-alanine chloromethylkeyone:Chloromethyl ketone inhibitor

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Most popular questions from this chapter

Calculate the rate enhancement that could be accomplished by an enzyme forming one low-barrier hydrogen bond with its transition state at 25C.

Why is the broad substrate specificity of chymotrypsin advantageous in vivo? Why would this be a disadvantage for some other proteases?

Draw a transition state diagram of (a) a non-enzymatic reaction and the corresponding enzyme-catalysed reaction in which (b) S binds loosely to the enzyme and (c) S binds very tightly to the enzyme. Compare ΔG‡ for each case. Why is tight binding of S not advantageous?

Using the reaction shown in Box 11-1 (the attack of an amine on thecarbonyl group of a ketone) as a starting point, draw curved arrows torepresent the base-catalyzed reaction (when the group —B: is present).

Which catalytic mechanism contributes the most to rate acceleration?
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