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For proline, unlike the other amino acids, the cis form is not so energetically

ID: 33144 • Letter: F

Question

For proline, unlike the other amino acids, the cis form is not so energetically unfavorable that it rarely occurs. In fact, some 10-40% of proline residues share a cis peptide bond with the prior amino acid residue, whereas among all other amino acid residues only 0.01% of peptide bonds are cis. Given this information, roughly how many times greater is the energetic penalty associated with assuming cis form for typical peptide bonds compared to those involving a proline residue at body temperature (37 C)? Approximate that 1/4 prolines are cis, and that the given percentages represent the thermodynamic equilibrium.

Explanation / Answer

The cis bonds of proline amino acids favor the formation of beta-stands of protein secondary structures. Because, it is a small amino acid and has imino-nitrogen group and the conversion of Trans form to Cis form is a thermodynamically favorable reaction. It is conformed, because about 6% of the peptide bonds involving the imino nitrogen of proline, however, are in the cis configuration, and many of these occur at turns.         

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