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Chapter 24: Q12P (page 1270)

Show how you would use a Strecker synthesis to make

  1. Leucine (b) Valine (c) Aspartic acid

Answer

Short Answer

Expert verified

(a)

Formation of leucine

(b)

Formation of valine

(c)

Formation of aspartic acid

Step by step solution

01

Formation of amino acids by Strecker synthesis

In Strecker synthesis, an aldehyde is treated with ammonia NH3,and then the addition of hydrogen cyanide HCN takes place,followed by hydrolysis H3O+to form the respective amide.

02

(a)

The Strecker synthesis for leucine is shown by the reaction given below:

Formation of leucine

(b)

The Strecker synthesis for valine is shown by the reaction given below:

Formation of valine

(c)

The Strecker synthesis for aspartic acid is shown by the reaction given below:

Formation of aspartic acid

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Most popular questions from this chapter

A molecular weight determination has shown that an unknown peptide is a pentapeptide, and an amino acid analysis shows that it contains the following residues: one Gly, two Ala, one Met, one Phe. Treatment of the original pentapeptide with carboxypeptidase gives alanine as the first free amino acid released. Sequential treatment of the pentapeptide with phenyl isothiocyanate followed by mild hydrolysis gives the following derivatives:

Propose a structure for the unknown pentapeptide.

Show the third and fourth steps in the sequencing of oxytocin. Use figure 24-14 as a guide.

After treatment with peroxyformic acid, the peptide hormone vasopressin is partially hydrolyzed. The following fragments are recovered. Propose a structure for vasopressin.

Phe-Gln-Asn Pro-Arg-Gly.NH2 Cys-Tyr-Phe

Asn-Cys-Pro-Arg Tyr-Phe-Gln-Asn

Most naturally occurring amino acids have chiral centers (the asymmetric α carbon atoms) that are named (S) by the Cahn-Ingold-Prelog convention (Section 5-3). The common naturally occurring form of cysteine has a chiral center that is named (R), however.

(a) What is the relationship between (R)-Cysteine and (S)-alanine? Do they have the opposite three-dimensional configuration (as the names might suggest) or the same configuration?

(b) (S)-Alanine is an L-amino acid (Figure 24-2). Is (R)-cysteine a D-amino acid or an L-amino acid?

There are many methods for activating a carboxylic acid in preparation for coupling with an amine. The following method converts the acid to an N-hydroxysuccinimide (NHS) ester.

(a) Explain why an NHS ester is much more reactive than a simple alkyl ester.

(b) Propose a mechanism for the reaction shown.

(c) Propose a mechanism for the reaction of the NHS ester with an amine, R-NH2
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