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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

Calculate the pI of each of the following amino acids:

a.asparagine b. arginine c. serine d. aspartate

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

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

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)?

A decapeptide undergoes partial hydrolysis to give peptides whose amino acid composition is shown. Reaction of the intact decapeptide with Edman鈥檚 reagent releases PTH-Gly. What is the sequence of the decapeptide?

1.Ala, Trp

2. Val,Pro,Asp

3. Pro, Val

4. Ala, Glu

5. Trp, Ala, Arg

6.Arg, Gly

7.Glu, Ala, Leu

8. Met, Pro, Leu, Glu
See all solutions

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