An Adventure in Stereochemistry

Alice in Mirror Image Land

By Frank J. Dinan, Gordon T. Yee

Abstract

Playfully alluding to Lewis Carroll’s tale of Alice Through the Looking Glass, this case study considers the problems that would arise if a person were to cross over into a mirror-image environment. Students read about a drowsy undergraduate studying for a stereochemistry exam who finds herself in a place where spearmint gum tastes like caraway seed. The case emphasizes the lock-and-key theory of enzyme action and stresses the need for molecules to have the proper chirality if they are to be biologically useful. Designed for introductory organic chemistry and biochemistry courses, the case could also be used in biology courses.

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Date Posted

08/30/2004

Overview

Objectives

Understand that a link exists between stereochemistry, taste, and smell.
Distinguish between chiral and achiral objects.
Apply the lock-and-key model of enzyme action.
Recognize that an enzyme capable of acting upon a chiral molecule won’t necessarily act on its enantiomer.
Distinguish between stereogenic and non-stereogenic carbon atoms.
Determine whether a wide variety of biologically important molecules are chiral or achiral.
Apply the Cahn-Ingold-Prelog system to determine the R- or S-designation of molecules.

Keywords

Stereochemistry; chirality; lock and key enzymes; enantiomer; stereogenic carbon atoms; taste; smell; Cahn-Ingold-Prelog

Subject Headings

Biochemistry

Organic Chemistry

EDUCATIONAL LEVEL

High school, Undergraduate lower division

FORMAT

PDF

TOPICAL AREAS

N/A

LANGUAGE

English

TYPE/METHODS

Directed