Glucono-delta-lactone (GDL), also known as gluconolactone, is an organic compound with the formula (HOCH)3(HOCH2CH)CO2. A colorless solid, it is an oxidized derivative of glucose.
It is typically produced by the aerobic oxidation of glucose in the presence of the enzyme
glucose oxidase. The conversion cogenerates
hydrogen peroxide, which is often the key product of the enzyme:
GDL has been marketed for use in
feta cheese.[7] GDL is pH-neutral, but hydrolyses in water to gluconic acid which is acidic, adding a tangy taste to foods, though it has roughly a third of the
sourness of
citric acid. It is metabolized to
6-phospho-D-gluconate; one gram of GDL yields roughly the same amount of
metabolic energy as one gram of
sugar.
Upon addition to water, GDL is partially
hydrolysed to gluconic acid, with the balance between the lactone form and the acid form established as a
chemical equilibrium. The rate of hydrolysis of GDL is increased by heat and high
pH.[8]
The yeast Saccharomyces bulderi can be used to ferment gluconolactone to ethanol and carbon dioxide. The pH value greatly affects culture growth. Gluconolactone at 1 or 2% in a mineral media solution causes the pH to drop below 3.[9]
^Pocker, Y.; Green, Edmond (1973). "Hydrolysis of D-Glucono-δ-lactone. I. General Acid–Base Catalysis, Solvent Deuterium Isotope Effects, and Transition State Characterization". J. Am. Chem. Soc. 95 (1): 113–19.
doi:
10.1021/ja00782a019.
PMID4682891.