β-D-galactopyranosyl-(1→4)-β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside | 4955-91-3

• 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→4)-β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside
• 英文别名: β-D-Gal-(1→4)-β-D-Fru-(2→1)-α-D-Glu；lactulosucrose；Gal(b1-4)Fruf(b2-1a)Glc；(2S,3R,4S,5R,6R)-2-[(2R,3S,4S,5S)-4-hydroxy-2,5-bis(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 4955-91-3
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: XSTKYFWHPDTKJT-APBKVMOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.8
• 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：

  蔗糖 、 乳果糖 在 Leuconostoc mesenteroides B-512F dextransucrase 、 calcium chloride 作用下， 以 aq. acetate buffer 为溶剂， 反应 48.0h， 以35%的产率得到β-D-galactopyranosyl-(1→4)-β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside
  参考文献：
  名称：

  Efficient Synthesis and Characterization of Lactulosucrose by Leuconostoc mesenteroides B-512F Dextransucrase

  摘要：

  This work describes an efficient enzymatic synthesis and NMR structural characterization of the trisaccharide beta-D-galactopyranosyl-(1-->4)-beta-D-fructofuranosyl-(2-->1)-alpha-D-glucopyranoside, also termed as lactulosucrose. This oligosaccharide was formed by the Leuconostoc mesenteroides B-512F dextransucrase-catalyzed transfer of the glucosyl residue from sucrose to the 2-hydroxyl group of the reducing unit of lactulose. The enzymatic reaction was carried out under optimal conditions, i.e., at 30 degrees C in 20 mM sodium acetate buffer with 0.34 mM CaCl2 at pH 5.2, and the effect of factors such as reaction time (0-48 h), enzyme charge (0.8, 1.6, and 2.4 U mL(-1)), and sucrose:lactulose concentration ratios (20:40, 30:30, and 40:20, expressed in g/100 mL) on the formation of transfer products were studied. The highest formation in lactulosucrose was attained at 8 and 24-32 h by using 20%:40% and 30%:30% sucrose:lactulose mixtures, respectively, with 1.6 or 2.4 U mL(-1) dextransucrase, leading to lactulosucrose yields of 27-35% in weight respect to the initial amount of lactulose. Furthermore, minor tetra- and pentasaccharide, both probably derived from lactulose, were also detected and quantified. Likewise, the capacity of lactulosucrose to act as D-glucosyl donor once the sucrose was consumed, could explain its decrease from 16 to 24 h when the highest charge of dextransucrase was used. Considering the chemical structure of the synthesized oligosaccharides, lactulosucrose and its derivatives could potentially be excellent candidates for an emerging prebiotic ingredient.

  DOI：

  10.1021/jf303335m

文献信息

• Efficient Synthesis and Characterization of Lactulosucrose by <i>Leuconostoc mesenteroides</i> B-512F Dextransucrase
  作者：Marina Díez-Municio、Miguel Herrero、Maria Luisa Jimeno、Agustín Olano、F. Javier Moreno

  DOI：10.1021/jf303335m

  日期：2012.10.24

  This work describes an efficient enzymatic synthesis and NMR structural characterization of the trisaccharide beta-D-galactopyranosyl-(1-->4)-beta-D-fructofuranosyl-(2-->1)-alpha-D-glucopyranoside, also termed as lactulosucrose. This oligosaccharide was formed by the Leuconostoc mesenteroides B-512F dextransucrase-catalyzed transfer of the glucosyl residue from sucrose to the 2-hydroxyl group of the reducing unit of lactulose. The enzymatic reaction was carried out under optimal conditions, i.e., at 30 degrees C in 20 mM sodium acetate buffer with 0.34 mM CaCl2 at pH 5.2, and the effect of factors such as reaction time (0-48 h), enzyme charge (0.8, 1.6, and 2.4 U mL(-1)), and sucrose:lactulose concentration ratios (20:40, 30:30, and 40:20, expressed in g/100 mL) on the formation of transfer products were studied. The highest formation in lactulosucrose was attained at 8 and 24-32 h by using 20%:40% and 30%:30% sucrose:lactulose mixtures, respectively, with 1.6 or 2.4 U mL(-1) dextransucrase, leading to lactulosucrose yields of 27-35% in weight respect to the initial amount of lactulose. Furthermore, minor tetra- and pentasaccharide, both probably derived from lactulose, were also detected and quantified. Likewise, the capacity of lactulosucrose to act as D-glucosyl donor once the sucrose was consumed, could explain its decrease from 16 to 24 h when the highest charge of dextransucrase was used. Considering the chemical structure of the synthesized oligosaccharides, lactulosucrose and its derivatives could potentially be excellent candidates for an emerging prebiotic ingredient.