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Chapter 29: 31P (page 1192)


Devise a synthesis of the following dipeptide from amino acid starting materials.



Short Answer

Expert verified

The general synthesis of dipeptide involves the reaction between two amino acids. The C-terminal and N-terminal amino acids can be identified based on the required dipeptide.

The respective functional groups can be protected by using suitable reagents and reacting.








Step by step solution

01

Synthesis of Dipeptide

The general synthesis of dipeptide involves the reaction between two amino acids. The C-terminal and N-terminal amino acids can be identified based on the required dipeptide.

The respective functional groups can be protected by using suitable reagents and reacting.

02

The required dipeptide structure





The structure of the Phe-Leu dipeptide is as shown below:


It has N-terminal phenylalanine and C-terminal Leucine.

So, the amine group in phenylalanine and the –COOH group of Leucine should be protected with the reagents Boc and benzyl alcohol, respectively.



03

Synthesis




The synthesis of Phe-Leuinvolves the below-shown steps:




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Most popular questions from this chapter

What amino acid is formed when CH3CONHCH(CO2Et)2is treated with the following series of reagents:

Deduce the sequence of a heptapeptide that contains the amino acids Ala, Arg, Glu, Gly, Leu, Phe, and Ser, from the following experimental data. Edman degradation cleaves Leu from the heptapeptide, and carboxypeptidase forms Glu and a hexapeptide. Treatment of the heptapeptide with chymotrypsin forms a hexapeptide and a single amino acid. Treatment of the heptapeptide with trypsin forms a pentapeptide and a dipeptide. Partial hydrolysis forms Glu, Leu, Phe, and the tripeptidesGly–Ala–Ser and Ala–Ser–Arg

Draw the products of each reaction.

(a)

(b)

(c)

(d)

What is the predominant form of each of the following amino acids at pH=11? What is the overall charge on the amino acid? (a)valine; (b)proline; (c)glutamic acid; (d)lysine?

Devise a synthesis of the following dipeptide from amino acid starting materials.
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