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Chapter 4: Q6CP (page 91)

Explain why all the amino acids except for glycine are chiral.

Short Answer

Expert verified

All the standard amino acids except for glycine are chiral because they all have four different substituents attached to their carbon (Cα) atom.

Step by step solution

01

Definition of chiral molecules

The molecules that are non-superimposable on their mirror images are called as chiral molecules and the central atom of such molecules are called chiral centers or asymmetric centers.The α-carbon of the standard amino acids are the chiral centres and are called chiral carbon, because the Cαis attached to 4 different groups that is an amino group (NH3), hydrogen atom (H), a carboxylic group (COO-) and a R-group.

02

Explain the reasoning

Amino acid glycine contains a carboxylic group, an amino group and two hydrogen atoms attached to its central α-carbon atom as shown in the figure below:

Structure of Glycine

Because glycine does not contain 4 different substituents, it is not chiral and is the only exception in all the amino acids.

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Most popular questions from this chapter

Draw the structure of Lys and Ala linked by an Isopeptide bond.

Some bacteria produce poly-γ-glutamic acid, a polymer in which the amino group of each glutamate residue is condensed with the γ-carboxylate group of the adjacent residue. Draw the repeating structure of this polymer.

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Draw the four stereoisomers of threonine as Fischer projections.

Taurine (2-aminoethanesulfonic acid) is sometimes called an amino acid.

(a) Explain why this designation is not valid. (b) From which of the 20 standard amino acids is taurine derived? Describe the chemical change(s) that occurred.
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