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Chapter 29: Q7. (page 1158)

What amino acid is formed whenCH3CONHCH(CO2Et)2is treated with the following series of reagents:

1NaOEt

role="math" localid="1648630585393" 2CH2=O

3H3O+,∆

Short Answer

Expert verified

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Step by step solution

01

Serine

Serine is one of the 20 amino acids found in many proteins, and contains amino, carboxyl, and alcohol group.Serine is a water-loving amino acid, which is why it is a polar hydrophilic amino acid.

02

Reagents

NaOEt acts as co-enzymes for the reaction, formaldehyde is used for preservation and hydrolysis is used to break down by adding water molecules that makes the solution acidic.

03

Reaction

When diethyl acetamidomalonate is treated with ,NaOEtCH2=Oundergoes hydrolysis and heat is given forms serine amino acid.

Formation of serine

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Most popular questions from this chapter

The fibroin proteins found in silk fibers consist of large regions of β-pleated sheets stacked one on top of another. (a) Explain why having a glycine at every other residue allows the β-pleated sheets to stack on top of each other. (b) Why are silk fibers insoluble in water?

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

The anti-obesity drug orlistat works by irreversibly inhibiting pancreatic lipase, an enzyme responsible for the hydrolysis of triacylglycerols in the intestines, so they are excreted without metabolism, inhibition occurs by reaction of orlistat with a serine residue of the enzyme, forming a covalently bound, inactive enzyme product. Draw the structure of the product formed during inhibition.

Name each peptide using both the one-letter and the three-letter abbreviations for the names of the component amino acids.

a.

b.

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.
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