Skip to main content
Ch.18 Amino Acids and Proteins
Chapter 18, Problem 18.10

Is serine chiral? Draw serine and identify the chiral atom. Explain why serine is chiral.

Verified step by step guidance
1
Draw the structure of serine, which is an amino acid with the formula C3H7NO3.
Identify the central carbon atom in the structure, which is bonded to four different groups: an amino group (NH2), a carboxyl group (COOH), a hydrogen atom (H), and a side chain (CH2OH).
Recognize that a chiral molecule has at least one carbon atom bonded to four different groups, making it asymmetric and non-superimposable on its mirror image.
Determine that the central carbon atom in serine is the chiral center because it is bonded to four different groups.
Conclude that serine is chiral because it contains a chiral center, making it capable of existing in two enantiomeric forms (L-serine and D-serine).

Verified Solution

Video duration:
0m:0s
This video solution was recommended by our tutors as helpful for the problem above.
Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Chirality

Chirality refers to the property of a molecule that makes it non-superimposable on its mirror image. A chiral molecule typically has at least one carbon atom bonded to four different substituents, creating two distinct forms known as enantiomers. This concept is crucial in understanding the behavior of molecules in biological systems, as chirality can influence how substances interact with enzymes and receptors.
Recommended video:
Guided course
1:39
Chirality Example 1

Amino Acids

Amino acids are organic compounds that serve as the building blocks of proteins. Each amino acid consists of a central carbon atom, an amino group, a carboxyl group, a hydrogen atom, and a variable side chain (R group). In the case of serine, the side chain contains a hydroxymethyl group, which contributes to its unique properties and its classification as a polar amino acid.
Recommended video:
Guided course
3:03
Amino Acid Catabolism: Amino Group Example 2

Chiral Center

A chiral center, often a carbon atom, is a point in a molecule where four different groups are attached, leading to chirality. In serine, the chiral center is the alpha carbon, which is bonded to an amino group, a carboxyl group, a hydrogen atom, and a hydroxymethyl side chain. The presence of this chiral center is what makes serine a chiral molecule, allowing it to exist in two enantiomeric forms.
Recommended video:
Guided course
2:37
Chirality Concept 1