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Chapter 21: Q24P (page 1002)

What amino acid is formed when the aldehyde used in the Strecker synthesis is

a. acetaldehyde? b. 2-methylbutanal? c. 3-methylbutanal?

Short Answer

Expert verified

In Strecker synthesis, an aldehyde reacts with ammonia to form an imine. A nucleophilic addition reaction with cyanide ion forms an intermediate, which, when hydrolyzed, forms the amino acid.

Step by step solution

01

Strecker synthesis

In Strecker synthesis, an aldehyde reacts with ammonia to form an imine. A nucleophilic addition reaction with cyanide ion forms an intermediate, which, when hydrolyzed, forms the amino acid.

02

Formation of respective amino acids

a)

Treatment of acetaldehyde with HCN produces the corresponding 伪-aminonitrile which upon hydrolysis produces alanine. The reaction is as follows:

b)

Treatment of 2-methyl butanal with HCN produces the corresponding -amino nitrile which upon hydrolysis produces isoleucine. The reaction is as follows:

c)

Treatment of 3-methyl butanal with HCN produces the corresponding 伪-aminonitrile which upon hydrolysis produces leucine. The reaction is as follows:

Formation of leucine (c)

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Most popular questions from this chapter

What is the configuration about each of the asymmetric centres in aspartame?

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

Explain why the pI of lysine is the average of the pKa values of its two protonated amino groups.

Alanine has pKa values of 2.34 and 9.69. Therefore, alanine exists predominately as a zwitterion in an aqueous solution with pH > ____ and pH < ____.

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?
See all solutions

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