stereoisomer

Same atoms, different arrangement

A stereoisomer is a molecule that has the same chemical formula and atomic connections as another but differs in how atoms are arranged in three-dimensional space.

Two stereoisomers are like a left hand and right hand—same parts, same connections, but mirror images that can't be superimposed.

The distinction matters in chemistry and pharmacology because stereoisomers often behave differently in biological systems: One stereoisomer of thalidomide treats morning sickness; the other causes birth defects.

chirality

enantiomer

Mirror-image molecular variant

handedness · mirror image · superimposable · R/S configuration

configuration

cis

On this side

conformer · axial · equatorial · anti · gauche · eclipsed · staggered · tautomer · meso compound · Fischer projection

biochemistry

thalidomide

Sedative causing fetal deformities

sugar · nucleotide · biosynthesis · glycoside · peptide · lipid

analysis

specific rotation

Standardized optical activity measure

Categories
Opposites
type of isomerism

stereoisomertautomer

Interconverting molecular form

molecular identity

stereoisomerhomolog

Corresponding genetic or anatomical element

Family

isotope, isomer, isosceles, isothermal, isomers, stereophonic, isomerization, isobaric, stereoscope

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