X-gal (5-bromo-4-chloro-3-indolyl-β-D-galactopyranoside)

X-gal (5-bromo-4-chloro-3-indolyl-β-D-galactopyranoside) is an organic compound consisting of galactose linked to a substituted indole. X-gal is an analog of lactose, and therefore is hydrolyzed by the β-galactosidase enzyme which cleaves the β-glycosidic bond in D-lactose. X-gal, when cleaved by β-galactosidase, yields galactose and 5-bromo-4-chloro-3-hydroxyindole. The latter then spontaneously dimerizes and is oxidized into 5,5'-dibromo-4,4'-dichloro-indigo, an intensely blue product which is insoluble. X-gal is colorless, so the presence of blue-colored products may therefore be used as a test for the presence of active β-galactosidase. This also allows for bacterial β-galactosidase (lacZ) to be used as a reporter in various applications.
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