a. Which isomer—(R)-alanine or (S)-alanine—is d-alanine?

b. Which isomer—(R)-aspartate or (S)-aspartate—is d-aspartate?

c. Can a general statement be made relating R and S to d and l?

Short Answer

Expert verified

a. Isomer—(R)-alanine is D-alanine.

b. Isomer—(R)-aspartate is D-aspartate

c. The α-carbon of all the naturally occurring D-amino acids except cysteine have the R-configuration. Similarly, the α-carbon of all the naturally occurring L-amino acids except cysteine has the S-configuration.

Step by step solution

01

Configuration of Amino acids

Amino acid is an organic molecule having carboxyl and amino group that combines to form proteins.The α-carbon of all the naturally occurring amino acids (except glycine) is an asymmetric center, therefore, 19 of the 20 amino acids can exist as enantiomers (having mirror images of each other).

The D and L notation used for monosaccharides, is also used for amino acids. Unlike monosaccharides, where the D-isomer is the one found in nature, most amino acids found in nature have the L configuration

An amino acid drawn in a Fischer projection with the carboxyl group at the top and the R group at the bottom of the vertical axis refers to a D-amino acid if the amino group is on the right.

An amino acid drawn in a Fischer projection with the carboxyl group at the top and the R group at the bottom of the vertical axis refers to an L-amino acid if the amino group is on the left in its Fischer projection.

02

Identify (a) and (b)

In a Fischer projection, horizontal lines project out of the plane of the paper toward the viewer, and vertical lines extend back from the plane of the paper away from the viewer.

a. Isomer—(R)-alanine is D-alanine. In, (R)-alanine, counterclockwise signifies R because the lowest priority substituent (H) is on a horizontal bond. Therefore, we change the configuration from S to R.

b. Isomer—(R)-aspartate is D-aspartate. In, (R)-aspartate, counterclockwise signifiesRbecause the lowest priority substituent (H) is on a horizontal bond. Therefore, we change the configuration from S to R.

03

General statement relating R and S to D and L

D and L is a relative configuration that can be measured by determining whether the substance rotates the plane-polarized light counterclockwise or clockwise, whereas R and S (absolute configuration) refers to the structural difference between stereoisomers.

The α-carbon of all the naturally occurring D-amino acids except cysteine has the R-configuration. Similarly, the α-carbon of all the naturally occurring L-amino acids except cysteine has the S-configuration.

The amino group has the highest priority and the carboxyl group has the second-highest priority in all the amino acids except cysteine. Because in cysteine, the thiomethyl group has the highest priority than the carboxylate group, due to the greater atomic number of sulfur as compared to oxygen, causing the counter clock-wise arrow to be clock-wise.

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Most popular questions from this chapter

What amino acid is formed using the N-phthalimidomalonic ester synthesis when the following alkyl halides are used in the third step?

(a)

(b) CH3SCH2CH2Br

After the polypeptide shown below was treated with maleic anhydride, it was hydrolyzed by trypsin. (After a polypeptide is treated with maleic anhydride,

trypsin will cleave the polypeptide only on the C-side of arginine.)

Gly-Ala-Asp-Ala-Leu-Pro-Gly-Ile-Leu-Val-Arg-Asp-Val-Gly-Lys-Val-Glu-Val-Phe-Glu-Ala-Gly-

Arg-Ala-Glu-Phe-Lys-Glu-Pro-Arg-Leu-Val-Met-Lys-Val-Glu-Gly-Arg-Pro-Val-Gly-Ala-Gly-Leu-Trp

a. After a polypeptide is treated with maleic anhydride, why does trypsin no longer cleave it on the C-side of lysine?

b. How many fragments are obtained from the polypeptide?

c. In what order will the fragments be eluted from an anion-exchange column using a buffer of pH = 5?

A professor was preparing a manuscript for publication in which she reported that the pI of the tripeptide Lys-Lys-Lys was 10.6. One of her studentspointed out that there must be an error in her calculations because the pKa of the e-amino group of lysine is 10.8 and the pI of the tripeptide has to begreater than any of its individual pKa values. Was the student correct?

The aldonic acid of D-glucose forms a five-membered-ring lactone. Draw its structure.

Cells can also convert a-keto acids into amino acids, but because the reagents organic chemists use for this reaction are not available in cells, they carry out this reaction by a different mechanism

(a) What amino acid is obtained from the reductive amination of each of the following metabolic intermediates in a cell by reductive amination?



(b)What amino acids are obtained from the same metabolic intermediates when the amino acids are synthesized in the laboratory?

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