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Draw all the steps in the synthesis of each peptide from individual amino acids:

  1. Gly-Ala;

  2. Ile-Ala-Phe

Short Answer

Expert verified

The synthesis of a peptide is done by protecting the amino group of one amino acid with Boc or Fmoc group and protecting the carboxyl group of another amino acid as an ester.

After this, it is treated with DCC and then, removal of both protecting groups is done.

Step by step solution

01

Synthesis of a peptide from amino acids

The synthesis of a peptide is done by protecting the amino group of one amino acid with Boc or Fmoc group and protecting the carboxyl group of another amino acid as an ester.

After this, it is treated with DCC and then, removal of both protecting groups is done.

02

Synthesis of Gly-Ala

In this reaction, protection of Gly is done as a Boc derivative, and protection of carboxy group in Ala as an ester is done. A and B products then form an amide bond with DCC. After this, it reacts with HBr and CH3COOHto form Gly-Ala.

03

Synthesis of Ile-Ala-Phe

In this reaction, protection of Ile is done as a Boc derivative, and protection of carboxy group in Ala as an ester is done. A and B products then form an amide bond when treated with DCC. After this, it undergoes elimination using H2and Pd catalyst to form C.

The protection of the carboxyl group in Phe as an ester is done. Now, this ester is treated with C and DCC. The compound formed further reacts with HBr and CH3COOHforms Ile-Ala-Phe.

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Most popular questions from this chapter

Consider the decapeptide angiotensin I.

  1. What products are formed when angiotensin I is treated with trypsin?
  2. What products are formed when angiotensin I is treated with chymotrypsin?
  1. Treatment of angiotensin I with ACE (the angiotensin-converting enzyme) cleaves only the amide bond with the carbonyl group derived from phenylalanine to afford two products.

The larger polypeptide is angiotensin II, a hormone that narrows blood vessels and increases blood pressure. Give the amino acid sequence of angiotensin II using threeletter abbreviations. ACE inhibitors are drugs that lower blood pressure by inhibiting the ACE enzyme (Problem 5.15).

What steps are needed to convert A to L-dopa, an uncommon amino acid that is effective in treating Parkinson’s disease? These steps are the key reactions in the first commercial asymmetric synthesis using a chiral transition metal catalyst. This process was developed at Monsanto in 1974.

L-thyroxine, a thyroid hormone and oral medication used to treat thyroid hormone deficiency, is an amino acid that does not exist in proteins. Draw the zwitterionic form of L-thyroxine.

a.(S)-Penicillamine, an amino acid that does not occur in proteins, is used as a copper chelating agent to treat Wilson’s disease, an inherited defect in copper metabolism.

(R)-Penicillamine is toxic, sometimes causing blindness. Draw the structures of (R) and (S)-penicillamine.

b. What disulfide is formed from oxidation of L-penicillamine?

Draw the structure for each peptide:

(a) Phe–Ala;

(b) Gly–Gln;

(c) Lys–Gly;

(d) R-H

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