Problemas sobre aminoácidos e peptídeos

PROBLEM 27.5 Outline the steps in a synthesis of valine from 3-methylbutanoic acid.

PROBLEM 27.6 Outline the steps in the preparation of valine by the Strecker synthesis.

PROBLEM 27.7 Outline the steps in the synthesis of valine from diethyl acetamidomalonate. The
overall yield of valine by this method is reported to be rather low (31%). Can you think of a reason
why this synthesis is not very efficient?

PROBLEM 27.8 Suggest a reasonable mechanism for the reaction of an α-amino acid with
ninhydrin.

PROBLEM 27.10 Write structural formulas showing the constitution of each of the following
dipeptides.

(a) Gly-Ala (b) Ala-Phe (c) Phe-Ala (d) Gly-Glu (e) Lys-Gly (f) D-Ala-D-Ala

PROBLEM 27.11 Expand your answer to Problem 27.10 by showing the structural formula for each
dipeptide in a manner that reveals the stereochemistry at the 𝛼-carbon atom.

PROBLEM 27.14 Amino acid analysis of a certain tetrapeptide gave alanine, glycine,
phenylalanine, and valine in equimolar amounts. Digestion of the tetrapeptide with chymotrypsin
gave a dipeptide that on amino acid analysis gave phenylalanine and valine. What amino acid
sequences are possible for the tetrapeptide?

PROBLEM 27.15 Give the structure of the phenylthiohydantoin derivative isolated in the second
Edman cycle of the tetrapeptide Val-Phe-Gly-Ala.

PROBLEM 27.16 Lysine reacts with two equivalents of benzyloxycarbonyl chloride to give a
derivative containing two benzyloxycarbonyl groups. What is the structure of this compound?
PROBLEM 27.17 Show the steps involved in the synthesis of Ala-Leu from alanine and leucine
using benzyloxycarbonyl and benzyl ester protecting groups and DCC-promoted peptide bond
formation.

PROBLEM 27.20 Starting with phenylalanine and glycine, outline the steps in the preparation of
Phe-Gly by the Merrifield method.