Chapter 29: Q40. (page 1193)
What alkyl halide is needed to synthesize each amino acid from diethyl acetamidomalonate: (a)Asn; (b)His; (c)Trp?
Chapter 29: Q40. (page 1193)
What alkyl halide is needed to synthesize each amino acid from diethyl acetamidomalonate: (a)Asn; (b)His; (c)Trp?
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Get started for freeUse the given experimental data to deduce the sequence of an octapeptide that contains the following amino acids: Ala, Gly (2 equiv), His (2 equiv), Ile, Leu and Phe. Edman degradation cleaves Gly from the octapeptide, and carboxypeptidase forms Leu and a heptapeptide. Partial hydrolysis forms the following fragments: Ile-His-Leu, Gly, Gly-Ala-Phe-His, and Phe-His-Ile.
Question: Identify A and B, isomers of molecular formula \({{\bf{C}}_{\bf{3}}}{{\bf{H}}_{\bf{4}}}{\bf{C}}{{\bf{l}}_{\bf{2}}}\), from the given \({}^{\bf{1}}{\bf{H}}\)NMR data: Compound A exhibits signals at 1.75 (doublet, 3H,\({\bf{J = 6}}{\bf{.9 Hz}}\)) and 5.89 (quartet, \({}^{\bf{1}}{\bf{H}}\),\({\bf{J = 6}}{\bf{.9 Hz}}\)) ppm. Compound B exhibits signals at 4.16 (singlet, 2 H), 5.42 (doublet, \({}^{\bf{1}}{\bf{H}}\),\({\bf{J = 1}}{\bf{.9 Hz}}\)), and 5.59 (doublet, \({}^{\bf{1}}{\bf{H}}\), \({\bf{J = 1}}{\bf{.9 Hz}}\)) ppm.
What form exists at the isoelectric point of each of the following amino acids: (a) valine; (b)leucine; (c)proline; (d) glutamic acid.
Question: Identify the functional groups in each molecule. Classify each alcohol, alkyl halide, amide, and amine as 1ยฐ, 2ยฐ, or 3ยฐ
a.
b.
c.
d.
e.
f.
Another method to form a peptide bond involves a two-step process:
[1] Conversion of a Boc-protected amino acid to a p-nitrophenyl ester.
[2] Reaction of the p-nitrophenyl ester with an amino acid ester.
Why does a p-nitrophenyl ester โactivateโ the carboxy group of the first amino acid to amide formation?
Would a p-methoxyphenyl ester perform the same function? Why or why not?
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