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Chapter 24: Q-24-35P (page 1298)

The following structure is drawn in an unconventional manner.

(a) Label the N terminus and the C terminus.

(b) Label the peptide bonds.

(c) Identify and label each amino acid present.

(d) Give the full name and the abbreviated name

Short Answer

Expert verified

Peptide bonds are denoted by asterisk (*)

Step by step solution

01

Step-1: Explanation to part (a)

N-terminus is referred to as the free amine end of the peptide chain and free carboxylic acid end is referred to as the C-terminus. Both the termini are different from each other with respect to chemical properties.

02

Step-2: Explanation to part(b)

Peptide bonds are formed when the amine group of one amino acid forms bond with carbonyl carbon of another amino acid. A chain of amino acids is known as polypeptide.

Peptide bonds are denoted with asterisks (*)

03

Step-3: Explanation to part(c)

Amino acids are building blocks of protein molecules. Proteins are broken or digested down into smaller molecules known as amino acids.

04

Step-4: Explanation to part (d)

Full name of the given polypeptide is glycylglutaminylisoleucinamide. Its abbreviated name is Gly-Gln-Ile. Naming of the polypeptide is done from N-terminus to C-terminus.

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Most popular questions from this chapter

Show how the following amino acids might be formed in the laboratory by reductive amination of the appropriate 伪-ketoacid.

Phenylalanine (b) Cysteine (c) Serine (d) Alanine

The Sanger method for N-terminus determination is a less common alternative to the Edman degradation. In the Sanger method, the peptide is treated with the Sanger reagent, 2,4-dinitrofluorobenzene, and then hydrolyzed by reaction with 6 M aqueous HCl. The N-terminal amino acid is recovered as its 2,4-dinitrophenyl derivative and identified.

(a)Propose a mechanism for the reaction of the N terminus of the peptide with 2,4-dinitrofluorobenzene.

(b) Explain why the Edman degradation is usually preferred over the Sanger method.

Peptides often have functional groups other than free amino groups at the N terminus and other than carboxyl groups at the C terminus.

(a) A tetrapeptide is hydrolyzed by heating with 6 M, and the hydrolysate is found to contain Ala, Phe, Val, and Glu. When the hydrolysate is neutralized, the odor of ammonia is detected. Explain where this ammonia might have been incorporated in the original peptide.

(b) The tripeptide thyrotropic hormone releasing factor(TRF) has the full name pyroglutamylhistidylprolinamide. The structure appears here. Explain the functional groups at the N terminus and at the C terminus.

(c)On acidic hydrolysis, an unknown pentapeptide gives glycine, alanine, valine, leucine and isoleucine. No odor of ammonia is detected when the hydrolysate is neutralized. Reaction with phenyl isothiocyanate followed by mild hydrolysis gives nophenylthiohydantoin derivative. Incubation with carboxypeptidase has no effect. Explain these findings.

Draw three-dimensional representation of the following amino acids:

(a) L-alanine

(b) L-Leucine

(c) D-serine

(d) D-glutamine


Show how you would use the Strecker synthesis to make isoleucine. What stereochemistry would you expect in your synthetic product?
See all solutions

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