Biotransformation of 1-naphthalenesulfonic acid by the green alga Scenedesmus obliquus.
Under sulfate limitation, axenic batch cultures of the green alga Scenedesmus obliquus metabolized 1-naphthalenesulfonic acid and partially used the sulfonate as a source of sulfur. The main metabolite, 1-hydroxy-2-naphthalenesulfonic acid, which was not metabolized further in the algal culture, was formed by hydroxylation of the substrate in position 1 and by migration of the sulfonic acid group to position 2 of the naphthalene ring (NIH shift). A smaller amount of 1-naphthalenesulfonic acid was desulfonated. The resulting 1-naphthol was mostly transformed into 1-naphthyl beta-d-glucopyranoside.
Kneifel
H
H
Institut für Chemie und Dynamik der Geosphäre 6, Forschungszentrum Jülich, D-52425 Jülich, Germany.
Elmendorff
K
K
Hegewald
E
E
Soeder
C J
CJ
D001711:Biotransformation; D000460:Chlorophyta / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D009282:Naphthalenesulfonates / Q000493:pharmacokinetics*
D009282:Naphthalenesulfonates