Chapter 29: Q10. (page 1162)
Which of the following amines can be used to resolve a racemic mixture of amino acids?
(a)
(b)

(c)

(d)

Short Answer
(c)
(d)

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Chapter 29: Q10. (page 1162)
Which of the following amines can be used to resolve a racemic mixture of amino acids?
(a)
(b)

(c)

(d)

(c)
(d)

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(a) What products are formed when each peptide is treated with trypsin? (b) What products are formed when each peptide is treated with chymotrypsin?
[1] Gly–Ala–Phe–Leu–Lys–Ala
[2] Phe–Tyr–Gly–Cys–Arg–Ser
[3] Thr–Pro–Lys–Glu–His–Gly–Phe–Cys–Trp–Val–Val–Phe
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.
What is the predominant form of each of the following amino acids at pH=11? What is the overall charge on the amino acid? (a)valine; (b)proline; (c)glutamic acid; (d)lysine?
Devise a stepwise synthesis of the tripeptide Val-leu-Val from 3-methylbutanal as the only organic starting material. You may also use any required inorganic or organic reagents.
Besides asymmetric hydrogenation (Section 29.4), several other methods are now available for the synthesis of optically active amino acids. How might a reaction like the Strecker synthesis be adapted to the preparation of chiral amino acids?
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