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Chapter 21: Q64P (page 1027)

Draw the product obtained when a lysine side chain in a polypeptide reacts with maleic anhydride.

Short Answer

Expert verified

There are 20 naturally occurring amino acids. Some different classifications of amino acids include acidic and basic amino acids. Lysine and arginine are basic amino acids that comprise two basic nitrogen-containing groups.

Step by step solution

01

Amino acids

There are 20 naturally occurring amino acids. Some different classifications of amino acids include acidic and basic amino acids. Lysine and arginine are basic amino acids that comprise two basic nitrogen-containing groups.

02

The product obtained when a lysine side chain in a polypeptide reacts with maleic anhydride

Lysine is a basic amino acid comprising a nitrogen group. Hence, it can react with an electrophilic position by providing the lone pair on the basic nitrogen.

The mechanism of lysine with maleic anhydride is given below.

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Most popular questions from this chapter

a. Why is the pKaof the glutamate side chain greater than the pKaof the aspartate side chain?

b. Why is the pKa of the arginine side chain greater than the pKa of the lysine side chain?

Which is the more effective buffer at physiological pH, a solution of 0.1 M glycylglycine or a solution of 0.2 M glycine?

After the polypeptide shown below was treated with maleic anhydride, it was hydrolyzed by trypsin. (After a polypeptide is treated with maleic anhydride,

trypsin will cleave the polypeptide only on the C-side of arginine.)

Gly-Ala-Asp-Ala-Leu-Pro-Gly-Ile-Leu-Val-Arg-Asp-Val-Gly-Lys-Val-Glu-Val-Phe-Glu-Ala-Gly-

Arg-Ala-Glu-Phe-Lys-Glu-Pro-Arg-Leu-Val-Met-Lys-Val-Glu-Gly-Arg-Pro-Val-Gly-Ala-Gly-Leu-Trp

a. After a polypeptide is treated with maleic anhydride, why does trypsin no longer cleave it on the C-side of lysine?

b. How many fragments are obtained from the polypeptide?

c. In what order will the fragments be eluted from an anion-exchange column using a buffer of pH = 5?

Why are the carboxylic acid groups of the amino acids more acidic

(pKa ~ 2) than a carboxylic acid such as acetic acid (pKa = 4.76)?

What aldehyde is formed when valine is treated with ninhydrin?
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