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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

The anti-obesity drug orlistat works by irreversibly inhibiting pancreatic lipase, an enzyme responsible for the hydrolysis of triacylglycerols in the intestines, so they are excreted without metabolism, inhibition occurs by reaction of orlistat with a serine residue of the enzyme, forming a covalently bound, inactive enzyme product. Draw the structure of the product formed during inhibition.

Explain why the pKaof the -NH3+group of an α-amino acid is lower than the pKaof the ammonium ion derived from a 1°amine (RNH3+). For example, pKaof the -NH3+group of alanine is 9.87 but the pKaof CH3NH3+is 10.63.

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

What types of stabilizing interactions exist between each of the following pairs of amino acids?

a. Ser and Tyr

b. Val and Leu

c. two Phe residues

Write out a scheme for the resolution of the two enantiomers of the antiplatelet drug clopidogrel with 10-camphorsulfonic acid.
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