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Chapter 29: Problem 29.48 (page 1194)

Brucine is a poisonous alkaloid obtained from Strychnosnux vomica, a tree that grows in India, Sri Lanka, and northern Australia. Write out a resolution scheme similar to the one given in Section 29.3A, which shows how a racemic mixture of phenylalanine can be resolved using brucine

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01

Brucine

Brucine comes under the category of alkaloids and is connected to strychnine. It is employed for stereospecific chemical syntheses in synthetic chemistry.

02

Resolution of a mixture of phenylalanine using brucine

The free amino group of the amino acid phenylalanine forms an amide bond on reaction with acetic anhydride. The product formed from the reaction is N-acetyl amino acid:

The reaction of phenylalanine with acetic anhydride

The enantiomers of phenylalanine undergo proton transfer with brucine to form diastereomers as:

Diastereomers formed by proton transfer

The physical and chemical properties of diastereomers are different from each other. The hydrolysis of diastereomers produces enantiomers of phenylalanine.

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Most popular questions from this chapter

Glutathione, a powerful antioxidant that destroys harmful oxidizing agents in cells, is composed of glutamic acid, cysteine, and glycine, and has the following structure:

Glutathione

a. What product is formed when glutathione reacts with an oxidizing agent?

b. What is unusual about the peptide bond between glutamic acid and cysteine?

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.

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.

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

Give the amino acid sequence of an octapeptide that contains the amino acids Tyr, Ala, Leu (2 equiv), Cys, Gly, Glu and Val, and forms the following fragments when partially hydrolyzed with HCl: Val-Cys-Gly-Glu, Ala-Leu-Tyr, and Tyr-Leu-Val-Cys.
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