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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 鈥揅OOH 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

Question: Draw the other three stereoisomers of L-isoleucine, and label the stereogenic centers as R or S.

An octapeptide contains the following amino acids: Arg, Glu, His, Ile, Leu, Phe, Tyr, and Val. Carboxypeptidase treatment of the octapeptide forms Phe and a heptapeptide. Treatment of the octapeptide with chymotrypsin forms two tetrapeptides, A and B. Treatment of A with trypsin yields two dipeptides, C and D. Edman degradation cleaves the following amino acids from each peptide: Glu (octapeptide), Glu (A), Ile (B), Glue (C), and Val (D). Partial hydrolysis of tetrapeptide B forms Ile-Leu in addition to other products. Deduce the structure of the octapeptide and fragments A-D.

(a) What products are formed when each peptide is treated with trypsin? (b) What products are formed when each peptide is treated with chymotrypsin?

[1] Gly鈥揂la鈥揚he鈥揕eu鈥揕ys鈥揂la

[2] Phe鈥揟yr鈥揋ly鈥揅ys鈥揂rg鈥揝er

[3] Thr鈥揚ro鈥揕ys鈥揋lu鈥揌is鈥揋ly鈥揚he鈥揅ys鈥揟rp鈥揤al鈥揤al鈥揚he

Draw the other three stereoisomers of L-isoleucine, and label the stereogenic centers as R or S.

What aldehyde is needed to synthesize each amino acid by the Strecker synthesis?

(a) Valine;

(b) Leucine;

(c) Phenylalanine.
See all solutions

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