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Chapter 29: Q30P (page 1191)

With reference to the following peptide:

(a) Identify the N-terminal and C-terminal amino acids.

(b) Name the peptide using one-letter abbreviations.

(c) Label all the amide bonds in the peptide backbone.

Short Answer

Expert verified

(a) The N-terminal amino acid is Alanine. In the given peptide, Alanine has a free anime group.

The N-terminal amino acid is Serine in the given peptide. It is the amino acid in which free carboxylic acid is present.

(b) The name of the peptide is Ser-Cys-Glu-Ala.

(c)

Tetrapeptide

Step by step solution

01

The given peptide

The given peptide has three amide bonds which represent it is a tetrapeptide.

The structure of the given peptide is as shown:

Tetrapeptide

02

The N-terminal amino acid

(a) The N-terminal amino acid is Alanine. In the given peptide, Alanine has a free amine group.

The N-terminal amino acid is Serine in the given peptide. It is the amino acid in which free carboxylic acid is present.

03

The name of the peptide

(b) The peptide given is a tetrapeptide with three amide bonds. Its structure and name is as shown:

Name of the peptide

04

The Amide bonds in the given peptide

(c) The amide bonds in the given peptide are marked and are as shown:

Tetrapeptide

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Most popular questions from this chapter

Which of the following amino acids are typically found in the interior of a globular protein, and which are typically found on the surface: (a)phenylalanine; (b)aspartic acid; (c) lysine; (d) isoleucine; (e) arginine; (f) glutamic acid?

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?

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.

Devise a stepwise synthesis of the tripeptide Val-leu-Val from 3-methylbutanal[CH32CHCH2CHO] as the only organic starting material. You may also use any required inorganic or organic reagents.

Another strategy used to resolve amino acids involves converting the carboxy group to an ester and then using a chiral carboxylic acid to carry out an acid-base reaction at the free amino group. Using a racemic mixture of alanine enantiomers and (R)-mandelic acid as resolving agent, write out the steps showing how a resolution process would occur.
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