Biotin is a white crystalline vitamin that is fairly stable when dry but can degrade in acidic or basic solutions. It has an essential chemical structure consisting of a planar ureido nucleus joined to a folded tetrahydrothiophene nucleus. Of its eight possible stereoisomers, only the d-isomer possesses biological activity. Biotin functions as a coenzyme by forming a covalent bond between its thiophane nucleus and the lysine residue of enzymes. Its ureido nucleus can become polarized and activated, increasing its nucleophilicity to allow biotin to transport carbon dioxide by binding the electrophilic carbonyl phosphate formed from bicarbonate and ATP.