Chapter 29: 65P (page 1197)
Draw the mechanism for the reaction that removes an Fmoc group from an amino acid under the following conditions:
Chapter 29: 65P (page 1197)
Draw the mechanism for the reaction that removes an Fmoc group from an amino acid under the following conditions:
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Get started for freeWrite out the steps for the synthesis of each peptide using the Merrifield method:
Besides the Boc and Fmoc protecting groups used in peptide synthesis, amines can also be protected by reaction with benzyl chloroformate (). Draw the structure of the product formed by reaction of alanine with benzyl chloroformate
Propose a structure consistent with each set of data.
a. Compound J: molecular ion at 72; IR peak at 1710 \({\bf{c}}{{\bf{m}}^{{\bf{ - 1}}}}\); \({}^{\bf{1}}{\bf{H}}\)-NMR data (ppm) at 1.0 (triplet, 3 H), 2.1 (singlet, 3 H), and 2.4 (quartet, 2 H)
b. Compound K: molecular ion at 88; IR peak at 3600–3200 \({\bf{c}}{{\bf{m}}^{{\bf{ - 1}}}}\); \({}^{\bf{1}}{\bf{H}}\)-NMR data (ppm) at 0.9 (triplet, 3 H), 1.2 (singlet, 6 H), 1.5 (quartet, 2 H), and 1.6 (singlet, 1 H)
Tryptophan is not classified as a basic amino acid even though it has a heterocycle containing a nitrogen atom. Why is the N atom in the five-membered ring of tryptophan not readily protonated by acid?
Devise a synthesis of each amino acid from acetaldehyde:
(a) Glycine;
(b) Alanine.
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