Logout Open In App
Open In App
Warning: foreach() argument must be of type array|object, bool given in /var/www/html/web/app/themes/studypress-core-theme/template-parts/header/mobile-offcanvas.php on line 20

Chapter 29: Q24. (page 1177)

Devise a synthesis of the following dipeptide from amino acid starting materials.

Short Answer

Expert verified

Protecting Group

Synthesis of Ala-Ser

Step by step solution

01

The given dipeptide

The given dipeptide has two amino acids, - alanine, and serine.

The structure of the required dipeptide is as shown:

Dipeptide

02

Protecting amine and carboxylic acid groups

The amine group in alanine is protected by using Boc(tertiary butyloxy carbonyl) reagent. The carboxylic acid group in serine is protected with bezyl alcohol as benzyl ester.

03

Synthesis

The amino acid alanine with a protected amino group, and the amino acid serine with a protected carboxylic acid group will react with each other and form the required dipeptide.

Protecting Groups

Synthesis of Ala-Ser

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Histidine is classified as a basic amino acid because one of the N atoms in its five-membered ring is readily protonated by acid. Which N atom in histidine is protonated and why?

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.

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.

Besides the Boc and Fmoc protecting groups used in peptide synthesis, amines can also be protected by reaction with benzyl chloroformate (C6H5CH2OCOCl). Draw the structure of the product formed by reaction of alanine with benzyl chloroformate

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?
See all solutions

Recommended explanations on Chemistry Textbooks

Inorganic Chemistry

Read Explanation

Organic Chemistry

Read Explanation

Chemical Reactions

Read Explanation

Chemical Analysis

Read Explanation

Chemistry Branches

Read Explanation

Physical Chemistry

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free