Chapter 29: Question 29.45 (page 1193)
Identify A–E in the following reaction sequence.

Short Answer
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Chapter 29: Question 29.45 (page 1193)
Identify A–E in the following reaction sequence.

Answer


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Identify the lettered intermediates in the following reaction scheme. This is an alternative method to synthesize amino acids, based on the Gabriel synthesis of 1° amines (Section 25.7A).

Question:Gramicidin S, a topical antibiotic produced by the bacterium Bacillus brevis, is a cyclic decapeptide formed from five amino acids. Draw the structures of the amino acids that form gramicidin S, and explain why this compound possesses two unusual structural features.

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.
Write out a scheme for the resolution of the two enantiomers of the antiplatelet drug clopidogrel with 10-camphorsulfonic acid.
Clopidogrel 10-camphorsulfonic acid
Write out the steps for the synthesis of each peptide using the Merrifield method:
(a)Ala-Leu-Phe-Phe;
(b) Phe-Gly-Ala-Ile.
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