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Question

The following statements are made with regard to the optical activity of amino acids derived from natural proteins:

A. All alpha-amino acids have the D stereochemical configuration.

B. All L-amino acids have the (S) absolute configuration except cysteine, which has the (R) absolute configuration.

C. All D-amino acids have the (S) absolute configuration except cysteine, which has the (R) stereochemical configuration.

D. In the absolute configuration system, L-threonine and L-isoleucine are (2S, 3R)-threonine and (2S, 3S)-isoleucine diastereomers, respectively.

Which one of the following options represents the combination of all correct statements?

The correct answer is

B and D

Let's analyze each statement regarding the optical activity and stereochemistry of amino acids derived from natural proteins.

Amino Acids Stereochemistry

Amino acids, except glycine, are chiral molecules containing a stereogenic center (chiral carbon) at the alpha-carbon. This chirality leads to optical activity and the possibility of different stereoisomers (D and L isomers).

Statement Analysis:

Statement A: All alpha-amino acids have the D stereochemical configuration.

This statement is incorrect. Natural proteins are primarily composed of L-alpha-amino acids. The D-amino acids are found in some peptides, cell walls of bacteria, and antibiotics, but are not the standard building blocks of proteins synthesized by ribosomes.

Statement B: All L-amino acids have the (S) absolute configuration except cysteine, which has the (R) absolute configuration.

This statement is generally correct. The L/D designation is based on the configuration relative to glyceraldehyde. The R/S designation is based on the Cahn-Ingold-Prelog priority rules applied to the groups around the chiral center. For most L-amino acids, following the priority rules (NH\(_2\) > COOH > R group > H), the configuration at the alpha-carbon is (S). However, in cysteine, the priority order is NH\(_2\) > CH\(_2\)SH > COOH > H. When determining the R/S configuration, if the lowest priority group (H) is pointing away, you trace from priority 1 to 2 to 3. For cysteine, this tracing goes clockwise, resulting in an (R) configuration, even though it is an L-amino acid. Thus, L-cysteine has the (R) absolute configuration.

Statement C: All D-amino acids have the (S) absolute configuration except cysteine, which has the (R) stereochemical configuration.

This statement is incorrect. D-amino acids generally have the (R) absolute configuration (except for D-cysteine, which would be (S)). The statement incorrectly mixes absolute (R/S) and stereochemical (D/L) configuration systems and incorrectly assigns (S) to D-amino acids in general.

Statement D: In the absolute configuration system, L-threonine and L-isoleucine are (2S, 3R)-threonine and (2S, 3S)-isoleucine diastereomers, respectively.

This statement is correct. Threonine and isoleucine are amino acids with two chiral centers (at the alpha-carbon, C2, and on the side chain, C3). For L-threonine, the configuration at C2 is (S) and at C3 is (R), making it (2S, 3R)-threonine. For L-isoleucine, the configuration at C2 is (S) and at C3 is (S), making it (2S, 3S)-isoleucine. Diastereomers are stereoisomers that are not mirror images of each other. Since L-threonine and L-isoleucine have different configurations at C3 while sharing the same configuration at C2, they are diastereomers.

Correct Statements Combination

Based on the analysis:

  • Statement A is incorrect.
  • Statement B is correct.
  • Statement C is incorrect.
  • Statement D is correct.

Therefore, the combination of all correct statements is B and D.

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Important Questions from Biochemistry

  1. The following table lists names of scientists and advances made by them

    Column AColumn B
    ALinus Pauling(i)Myoglobin structure
    BEmil Fischer(ii)Model of α-helix
    CJohn Kendrew(iii)Lock and Key model
    DChristian Anfinsen(iv)Sequence-structure

    Which one of the following options correctly matches contents of column A with column B?
  2. One gram of a polysaccharide composed of 1000 glucose units has the same effect on osmolarity as that of

  3. Several proteins are modified by phosphorylation at specific amino acid residues to alter their activities. Which one of the following amino acids is NOT typically a site of phosphorylation in proteins?

  4. How long should it take the polypeptide backbone of a 6-residue, 10-residue, 15-residue and 20-residue folding nucleus to explore all its possible conformations? Assume that the polypeptide backbone randomly reorients every 10-13 seconds (s).

  5. Lactose is the substrate for which of the following enzyme ?

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