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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

Reaction of a polypeptide with carboxypeptidase A releases Met. The polypeptide undergoes partial hydrolysis to give the following peptides.

What is the sequence of the polypeptide?

1. Ser, Lys, Trp4. Leu, Glu, Ser 7. Glu, His 10. Glu, His, Val

2. Gly, His, Ala 5. Met, Ala, Gly8. Leu, Lys, Trp11. Trp, Leu, Glu

3. Glu, Val, Ser 6. Ser, Lys, Val 9. Lys, Ser 12. Ala, Met

Draw the resonance contributors of the peptide bond in the less stable configuration.

a. What percentage of the 伪-amino group of lysine will be protonated at its pI?<25%50% >75%

b. Answer the same question for the蔚-amino group of lysine.

Draw the tetrapeptide Ala-Thr-Asp-Asn and indicate the peptide bonds.

Treatment of a polypeptide with 2-mercaptoethanol yields two polypeptides with the following primary structures:

Val-Met-Tyr-Ala-Cys-Ser-Phe-Ala-Glu-Ser

Ser-Cys-Phe-Lys-Cys-Trp-Lys-Tyr-Cys-Phe-Arg-Cys-Ser

Treatment of the original intact polypeptide with chymotrypsin yields the following peptides:

1. Ala, Glu, Ser 3. Tyr, Val, Met 5. Ser, Phe, 2 Cys, Lys, Ala, Trp

2. 2 Phe, 2 Cys, Ser 4. Arg, Ser, Cys 6. Tyr, Lys

Determine the positions of the disulfide bridges in the original polypeptide.
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