Although little was known about chemical chirality in the time of Lewis Carroll, his work Through the Looking-glass contains a prescient reference to the differing biological activities of enantiomeric drugs: "Perhaps Looking-glass milk isn't good to drink," Alice said to her cat.
In the Dorothy L. Sayers novel The Documents in the Case a murder is committed that is designed to appear to be accidental death caused by eating poisonous mushrooms containing muscarine. The case is proved to be murder because the muscarine found in the deceased's stomach is racemic and therefore synthetic.
In James Blish's Star Trek novella Spock Must Die! the tachyon 'mirrored' Mr Spock is later discovered to have stolen chemical reagents from the medical bay and to have been using them to convert certain amino acids to opposite-chirality isomers, since the mirrored Mr Spock's metabolism is reversed, and, hence, must process the opposite polarity of these isomers.
In Larry Niven's Destiny's Road, the title planet's indigenous life is based upon right-handed proteins. When human colonists arrive from Earth via a generation ship, extreme measures are taken to permit the colony's survival. A peninsula is sterilized with a lander's fusion drive, creating the titular "road" out of fused bedrock. The area is then reseeded with Earth life to provide the colonists with food. Though the soil lacks potassium due to other factors, necessitating supplements that produce a hydraulic empire common to Niven's fiction, the colony otherwise prospers. Native viruses and bacteria cannot infect colonists, resulting in longer lifespans. Sealife quickly recovers, and is consumed by the colonists as a "diet" food, as their digestive systems cannot metabolize it into fat.
Marti Steussy's "Dreams of Dawn" (1988) has a similar premise, where the locals evolved based on right-handed amino acids.
In the Trauma Center series of games, doctors test for a "chiral reaction" in order to determine whether or not a patient is infected with "Gangliated Utrophin Immuno Latency Toxin," a fictional, parasitic pathogen more commonly referred to as G.U.I.L.T. A positive reaction means the patient is infected, while a negative reaction means the patient has either been cured or is not infected.
In the video game Mass Effect, the turian and quarian alien races have biology based upon right-handed amino acids. Because of this foods from other races which have life forms based upon left-handed amino acids have no nutritional value and may cause fatal allergic reactions.
The denouement of Poul Anderson's After Doomsday relies partly on chirality.
The plot of Roger Zelazny's Doorways in the Sand centers around a device called the Rhennius Machine, any object passed through which will emerge its complete chiral opposite, down to the molecular level.