Eleven oligosaccharides formed by a transglycosylation reaction during lactose hydrolysis with Bacillus circulans β-galactosidase were purified by gel permeation chromatography, charcoal chromatography, and HPLC. From the results of methylation analysis, and MS and NMR studies, it was concluded that these oligosaccharides were β-D-Galp-(1→3)-D-Glc, β-D-Galp-(1→6)-D-Glc, β-D-Galp-(1→2)-D-Glc, β-D-Galp-(1→4)-β-D-Galp-(1→4)-D-Glc, β-D-Galp-(1→6)-[β-D-Galp-(1→2)]-D-Glc, β-D-Galp-(1→6)-[β-D-Galp-(1→4)]-D-Glc, β-D-Galp-(1→4)-β-D-Galp-(1→3)-D-Glc, β-D-Galp-(1→4)-β-D-Galp-(1→2)-D-Glc, β-D-Galp-(1→4)-[β-D-Galp-(1→2)]-D-Glc, β-D-Galp-(1→4)-β-D-Galp-(1→6)-D-Glc, β-D-Galp-(1→6)[β-D-Galp-(1→3)]-D-Glc. The last five are newly observed oligosaccharides. The results of a use test (in vitro) by human intestinal bacteria showed that the oligosaccharides containing lactose units were predominantly used by human intestinal bifidobacteria.

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