H. Kneifel et al., BIOTRANSFORMATION OF 1-NAPHTHALENESULFONIC ACID BY THE GREEN-ALGA SCENEDESMUS-OBLIQUUS, Archives of microbiology, 167(1), 1997, pp. 32-37
Under sulfate limitation, axenic batch cultures of the green alga Scen
edesmus obliquus metabolized 1-naphthalenesulfonic acid and partially
used the sulfonate as a source of sulfur. The main metabolite, 1-hydro
xy-2-naphthalenesulfonic acid, which was not metabolized further in th
e algal culture, was formed by hydroxylation of the substrate in posit
ion 1 and by migration of the sulfonic acid group to position 2 of the
naphthalene ring (NIH shift). A smaller amount of 1-naphthalenesulfon
ic acid was desulfonated. The resulting 1-naphthol was mostly transfor
med into 1-naphthyl beta-D-glucopyranoside.