β-D-galactopyranosyl-(1-6)-β-D-galactopyranosyl-(1-4)-β-D-fructofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-galactopyranosyl-(1-6)-β-D-galactopyranosyl-(1-4)-β-D-fructofuranose
• 英文别名: Gal(b1-6)Gal(b1-4)b-Fruf；(2R,3R,4S,5R,6R)-2-[[(2R,3R,4S,5R,6S)-6-[(2R,3S,4S,5R)-4,5-dihydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: OOTUVYHKHUAYAW-DCXHKWDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.6
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  269
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  乳果糖 在 β-galactosidase from Kluyveromyces lactis 、 magnesium chloride 作用下， 反应 6.0h， 生成 β-D-galactopyranosyl-(1-6)-β-D-galactopyranosyl-(1-4)-α-D-fructofuranose 、 β-D-galactopyranosyl-(1-6)-β-D-galactopyranosyl-(1-4)-β-D-fructofuranose 、 β-D-galactopyranosyl-(1-6)-β-D-galactopyranosyl-(1-4)-β-D-fructopyranose 、 β-D-galactopyranosyl-(1-4)-α-D-fructofuranosyl-(1-1)-β-D-galactopyranose 、 β-D-galactopyranosyl-(1-4)-β-D-fructofuranosyl-(1-1)-β-D-galactopyranose 、 β-D-galactopyranosyl-(1-4)-β-D-fructopyranosyl-(1-1)-β-D-galactopyranose
  参考文献：
  名称：

  Enzymatic Synthesis and Identification of Two Trisaccharides Produced from Lactulose by Transgalactosylation

  摘要：

  The enzymatic transgalactosylation during lactulose hydrolysis was studied using the beta-galactosidase from Kluyveromyces lactis and an initial lactulose concentration of 250 g/L. During hydrolysis of lactulose, the formation of two novel trisaccharids was followed by high-performance anion-exchange chromatography with pulsed amperometric detection (HPAEC-PAD). A maximum trisaccharide yield of 14.05% was observed at 91.9% of lactulose hydrolysis. The two novel trisaccharides obtained by transglycosylation of lactulose were isolated and fully characterized by an extensive nuclear magnetic resonance (NMR) study. Complete structure elucidation and full proton and carbon assignment were carried out using 1D (H-1, C-13, and 1D TOCSY) and 2D (gCOSY, TOCSY, ROESY, gHSQC, and gHMBC) NMR experiments. The trisaccharides were shown to be lactulose-based structures, the main one has a Gal unit linked to C-6 of the galactose moiety, and the other one has a Gal unit linked to C-1 of the fructose moiety. Transglycosylation of lactulose allows for the obtention of galactooligosaccharides with new glycosidic structures and would open new routes to the synthesis of prebiotics.

  DOI：

  10.1021/jf0721343

文献信息

• Enzymatic Synthesis and Identification of Two Trisaccharides Produced from Lactulose by Transgalactosylation
  作者：Cristina Martínez-Villaluenga、Alejandra Cardelle-Cobas、Agustín Olano、Nieves Corzo、Mar Villamiel、Maria Luisa Jimeno

  DOI：10.1021/jf0721343

  日期：2008.1.1

  The enzymatic transgalactosylation during lactulose hydrolysis was studied using the beta-galactosidase from Kluyveromyces lactis and an initial lactulose concentration of 250 g/L. During hydrolysis of lactulose, the formation of two novel trisaccharids was followed by high-performance anion-exchange chromatography with pulsed amperometric detection (HPAEC-PAD). A maximum trisaccharide yield of 14.05% was observed at 91.9% of lactulose hydrolysis. The two novel trisaccharides obtained by transglycosylation of lactulose were isolated and fully characterized by an extensive nuclear magnetic resonance (NMR) study. Complete structure elucidation and full proton and carbon assignment were carried out using 1D (H-1, C-13, and 1D TOCSY) and 2D (gCOSY, TOCSY, ROESY, gHSQC, and gHMBC) NMR experiments. The trisaccharides were shown to be lactulose-based structures, the main one has a Gal unit linked to C-6 of the galactose moiety, and the other one has a Gal unit linked to C-1 of the fructose moiety. Transglycosylation of lactulose allows for the obtention of galactooligosaccharides with new glycosidic structures and would open new routes to the synthesis of prebiotics.