Several pyridoxine compounds were found to be formed in a high yield in a growing culture of Sporobolomyces singularis containing lactose and pyridoxine. Three compounds, I, II and III, were isolated from cultured broth by Dowex 50W-X8 column chromatography, paper chromatography, lyophilization, and then obtained as needle crystals (m.p. (decomp.): I, 204-206 degrees C; II, 192-194 degrees C; III, 222-223 degrees C. [α]D16: I, -27.7 degrees (c = 3.82, H2O); II, -1.6 degrees (c = 2.52, H2O); III, +8.3 degrees (c = 3.98, H2O)). Compounds I, II and III were identified as 5'-O-(β-D-galactopyranosyl)-pyridoxine, 4'-O-(β-D-galactopyranosyl)-pyridoxine, and 4'-O-(β-D-galactopyranosyl-(1----4)-β-D-galactopyranosyl)-pyrid oxi ne, respectively, on the basis of the various experimental results, viz., ultraviolet, infra-red, 1H-NMR, and 13C-NMR spectra, products by hydrolysis with acid and with α- and β-galactosidases, migration on paper electrophoresis, and Gibbs reaction in the presence and absence of boric acid. Also, the yeast produced a remarkable amount of β-glucosyl compounds of pyridoxine in cultured broth, when grown on cellobiose and pyridoxine.

Pyridoxine 5′-β-galactoside, Pyridoxine 4′-β-galactoside, Pyridoxine 4′-β-galactobioside, S. singularis

1H NMR data:
missing...

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

Cc1ncc(CO)c(CO[C@@H]2O[C@H](CO)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)c1O

493.462 g/mol (C₂₀H₃₁NO₁₃)