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Chapter 29: Q44P (page 1193)

Glutamic acid is synthesized by the following reaction sequence. Draw a stepwise mechanism for Steps [1]–[3].

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01

Glutamic acid

Glutamic acid belongs to the amino acid family which is a non-essential amino acid consisting of amino and carboxylic group.It helps in cellular metabolism, improves heartbeat, remove toxic substances.

02

Mechanism of glutamic acid

In the first step, diethyl acetamidomalonate is treated with Sodium ethoxide, and it forms a compound with the removal of ethanol. In step 2, ethyl acrylate attacks the negatively charged carbon atom and forms a compound as shown below.

Then nucleophile attack to the compound an intermediate is formed in step 3.Finally, it undergoes hydrolysis to form glutamic acid.

Formation of glutamic acid

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Most popular questions from this chapter

Deduce the sequence of a heptapeptide that contains the amino acids Ala, Arg, Glu, Gly, Leu, Phe, and Ser, from the following experimental data. Edman degradation cleaves Leu from the heptapeptide, and carboxypeptidase forms Glu and a hexapeptide. Treatment of the heptapeptide with chymotrypsin forms a hexapeptide and a single amino acid. Treatment of the heptapeptide with trypsin forms a pentapeptide and a dipeptide. Partial hydrolysis forms Glu, Leu, Phe, and the tripeptidesGly–Ala–Ser and Ala–Ser–Arg

Draw the structure of the N-phenylthiohydantoin formed by initial Edman degradation of each peptide: (a) Ala-Gly-Phe-Phe; (b) Val-Ile-Tyr.

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?

Question: Identify A and B, isomers of molecular formula \({{\bf{C}}_{\bf{3}}}{{\bf{H}}_{\bf{4}}}{\bf{C}}{{\bf{l}}_{\bf{2}}}\), from the given \({}^{\bf{1}}{\bf{H}}\)NMR data: Compound A exhibits signals at 1.75 (doublet, 3H,\({\bf{J = 6}}{\bf{.9 Hz}}\)) and 5.89 (quartet, \({}^{\bf{1}}{\bf{H}}\),\({\bf{J = 6}}{\bf{.9 Hz}}\)) ppm. Compound B exhibits signals at 4.16 (singlet, 2 H), 5.42 (doublet, \({}^{\bf{1}}{\bf{H}}\),\({\bf{J = 1}}{\bf{.9 Hz}}\)), and 5.59 (doublet, \({}^{\bf{1}}{\bf{H}}\), \({\bf{J = 1}}{\bf{.9 Hz}}\)) ppm.

After the peptide chain of collage has been formed, many of the proline residues are hydroxylated on one of the ring carbon atoms. Why is this process important for the triple helix of collagen?

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