Chemoenzymatic Synthesis of .ALPHA.(a.RAR.3)-linked Galactooligosaccharides.

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  • α(1→3)結合したガラクトオリゴ糖の合成
  • Chemoenzymatic Synthesis of α(1→3)-linked Galactooligosaccharides
  • Chemoenzymatic Synthesis of アルファ 1 3 linked Galactooligosaccharides

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Abstract

Gal-α(1→3) -GalαpNP was regioselectively synthesized from para-nitrophenyl α-D-galactopyranoside (GalapNP) in 8.0% yield by the transglycosylation reaction, using α-galactosidase from Penicillium funiculosum. After conversion to an acetamidophenyl group, the para-nitrophenyl group was removed by using cerium ammonium nitrate (CAN). The heptaacetyl galactosyl disaccharide was converted to Gal-α (1→3) -Gal by deacetylation. To synthesize the trisaccharide, the heptaacetylgalactosyl disaccharide was converted to the trichloroacetimidate derivative, then coupled with a selectively protected GlcNAc derivative to give a trisaccharide derivative, which was then deprotected to provide Gal-α (1→3) -Gal-β(1→4) -GlcNAc.

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