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Chapter 24: Q16P. (page 1273)

Give equations for the formation and hydrogenolysis of N-benzyloxy carbonyl methionine.

Short Answer

Expert verified

Formation of N- benzyloxy carbonyl methionine

Hydrogenolysis of N-benzyloxy carbonyl methionine

Step by step solution

01

Acylation process

Anamino group is converted to an amide with the help of an acylating agent. In order to protect the amino group from unwanted nucleophilic substitution reactions, the acylation process is carried out. A large number of acid chlorides and anhydrides are used for acylation. The amino group is acylated by benzyl chloroformate to yield a benzyloxycarbonyl derivative, which is often used as a protecting group in peptide synthesis.

02

(a)

The equation for the formation of benzyloxycarbonyl methionine is as shown below:

Formation of N-benzyloxy carbonyl methionine

(b)

The equation for the hydrogenolysis of benzyloxycarbonyl methionine is as shown below:

Hydrogenolysis of N-benzyloxy carbonyl methionine

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Most popular questions from this chapter

A molecular weight determination has shown that an unknown peptide is a pentapeptide, and an amino acid analysis shows that it contains the following residues: one Gly, two Ala, one Met, one Phe. Treatment of the original pentapeptide with carboxypeptidase gives alanine as the first free amino acid released. Sequential treatment of the pentapeptide with phenyl isothiocyanate followed by mild hydrolysis gives the following derivatives:

Propose a structure for the unknown pentapeptide.

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 herbicide glyphosate(Roundup) kills plants by inhibiting an enzyme needed for synthesis of phenylalanine. Deprived of phenylalanine, the plant cannot make the proteins it needs, and it gradually weakens and dies. Although a small amount of glyphosate is deadly to a plant, its human toxicity is quite low. Suggest why this powerful herbicide has little effect on humans.

Draw the resonance forms of a protonated guanidino group and explain why arginine has such a strongly basic isoelectric point.

Suggest a method for the synthesis of the natural L enantiomer of alanine from the readily available L enantiomer of lactic acid.
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