Surprisingly, yes. cis-3,5-Diacetoxy-1-cyclopentene is a small, nearly symmetrical molecule used as a building block in organic synthesis. Its two acetate groups occupy equivalent-looking positions. In an ordinary chemical environment, choosing one instead of the other can be difficult.
But enzymes see molecules in three dimensions. A lipase can interact with this molecule so precisely that it selectively transforms one side while leaving the other alone. Suddenly, symmetry is gone.
Global Chemical Database