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Chapter 21: Q40P (page 1018)

Explain why cyanogens bromide does not cleave on the C-side of cysteine.

Short Answer

Expert verified

The answer is

Imine is not formed due to the difficulty in the formation of the strained four-membered ring.

Step by step solution

01

Step-by-Step Solution Step 1: Cysteine

The amino acids are the simple basic units of peptides and proteins. Cysteine is an amino acid containing a sulfur atom.

02

Explanations

The structure of cysteine is given below.

Cysteine can react with cyanogens bromide, and the sulfur will not be positively charged, hence a poor leaving group. In addition, the lactone will not be formed as it would have a strained four-membered ring. The imine will not be formed without lactone formation, and therefore, the cleavage cannot occur.

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Most popular questions from this chapter

a. Calculate the overall yield of bradykinin when the yield for the addition of each amino acid to the chain is 70%.

b. What would be the overall yield of a peptide containing 15 amino acids if the yield for the incorporation of each is 80%?

Why are buffer solutions of increasingly higher pH used to elute the column that generates the chromatogram shown in Figure 21.5? (Elutemeans wash out with a solvent.)

Draw the form of aspartate that predominates at the following pH values:

a. pH = 1.0 b. pH = 2.6 c. pH = 6.0 d. pH = 11.0

a. Why is the pKaof the glutamate side chain greater than the pKaof the aspartate side chain?

b. Why is the pKa of the arginine side chain greater than the pKa of the lysine side chain?

Draw the tetrapeptide Ala-Thr-Asp-Asn and indicate the peptide bonds.
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