O-β-D-fructofuranosyl-(2->1)-O-β-D-fructofuranosyl-(2->1)-O-[β-D-galactopyranosyl-(1->4)]-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-β-D-fructofuranosyl-(2->1)-O-β-D-fructofuranosyl-(2->1)-O-[β-D-galactopyranosyl-(1->4)]-α-D-glucopyranoside
• 英文别名: β-D-galactopyranosyl-(1->4)-α-D-glucopyranosyl-(1->2)-β-D-frustofuranosyl-(1->2)-β-D-fructofuranoside；O-β-D-fructofuranosyl-(2->1)-β-D-fructofuranosyl-O-[β-D-galactopyranosyl-(1->4)]-α-D-glucopyranoside；1^F-β-D-fructofuranosyl-4^G-β-D-galactopyranosylsucrose；monofructosyllactosucrose；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-6-[(2S,3S,4S,5R)-2-[[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₄H₄₂O₂₁
• 分子量: 666.585
• InChiKey: GHJWKHWSLFWEOS-ULYYFHRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.7
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  348
• 氢给体数：
  14
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  Lactose 、 蔗果三糖 在 β-galactosidase from Bacillus circulans (EC 3.2.1.23) 作用下， 以 acetate buffer 为溶剂， 反应 2.0h， 以32%的产率得到O-β-D-fructofuranosyl-(2->1)-O-β-D-fructofuranosyl-(2->1)-O-[β-D-galactopyranosyl-(1->4)]-α-D-glucopyranoside
  参考文献：
  名称：

  环状芽孢杆菌β-半乳糖苷酶区域选择性合成半乳糖基化三糖和四糖

  摘要：

  来自环状芽孢杆菌的 β-半乳糖苷酶 (EC 3.2.1.23) 催化半乳糖单位向各种葡萄糖和半乳糖衍生物的转移，形成 β1→4 键。几种生物学相关的三糖和四糖的合成{β-D-Galp-(1→4)-β-D-Galp-(1→4)-α,β-D-Glcp (2), β-D- Galp-(1→4)-α-D-Glcp-(1→4)-D-Glcp-ol/Manp-ol(4)、β-D-Galp-(1→4)-α-D-Glcp -(1→6)-β-D-Fruf (6), β-D-Galp-(1→4)-α-D-Glcp-(1↔2)-β-D-Fruf (8), β -D-Galp-(1→4)-α-D-Glcp-(1↔2)-β-D-Fruf-(1↔2)-β-D-Fruf (10), β-D-Galp- (1→4)-α-D-Glcp-(1→6)-[α-D-Glcp-(1↔2)]-β-D-Fruf (12a), β-D-Galp-(1→

  DOI：

  10.1055/s-2003-38075

文献信息

• Two Novel Oligosaccharides Formed by 1^F-Fructosyltransferase Purified from Roots of Asparagus (<i>Asparagus officinalis</i>L.)
  作者：Akira YAMAMORI、Shuichi ONODERA、Masanori KIKUCHI、Norio SHIOMI

  DOI：10.1271/bbb.66.1419

  日期：2002.1

  Two novel oligosaccharides, tetra-and penta-saccharides were synthesized by fructosyl transfer from 1-kestose to 4G-β-D-galactopyranosylsucrose with a purified 1F-fructosyltransferase of asparagus roots and identified as 1F-β-D-fructofuranosyl-4G-β-D-galactopyranosylsucrose, O-β-D-fructofuranosyl-(2→1)-β-D-fructofurano-syl-O-[β-D-galactopyranosyl-(1→4)]-α-D-glucopyranoside and 1F(1-β-D-fructofuranosyl)2-4G-β-D-galactopyranosylsucrose, [O-β-D-fructofuranosyl-(2→1)]2-β-D-fructofuranosyl-O-[β-D-galactopyranosyl-(1→4)]-α-D-glucopyranoside, respectively. Both oligosaccharides were scarcely hydrolyzed by carbohydrase from rat small intestine.Human intestinal bacterial growth by 1F-β-D-fructofuranosyl-4G-β-D-galactopyranosylsucrose was compared with that by the tetrasaccharides, stachyose and nystose. Bifidobacteria utilized 1F-β-D-fructofuranosyl-4G-β-D-galactopyranosylsucrose to the same extent as stachyose or nystose. On the other hand, the unfavorable bacteria, Clostridium perfringens, Escherichia coli and Enterococcus faecalis, that produce mutagenic substances did not use the synthetic oligosaccharide.

  两种新型低聚糖——四糖和五糖是通过从1-kestose到4G-β-D-galactopyranosylsucrose的果糖基转移，用芦笋根中纯化的1F-果糖基转移酶合成的，并分别命名为1F-β-D-fructofuranosyl-4G-β-D-galactopyranosylsucrose、O-β-D-fructofuranosyl-(2→1)-β-D-fructofurano-syl-O-[β-D-galactopyranosyl-(1→4)]-α-D-glucopyranoside和1F(1-β-D-fructofuranosyl)2-4G-β-D-galactopyranosylsucrose、[O-β-D-fructofuranosyl-(2→1)]2-β-D-fructofuranosyl-O-[β-D-galactopyranosyl-(1→4)]-α-D-glucopyranoside。这两种低聚糖几乎不会被大鼠小肠中的碳水化合物酶水解。将1F-β-D-fructofuranosyl-4G-β-D-galactopyranosylsucrose与四
• Regioselective Synthesis of Galactosylated Tri- and Tetrasaccharides by Use of β-Galactosidase from<i>Bacillus circulans</i>
  作者：Joachim Thiem、Erzsébet Farkas、Ulja Schmidt、Jörg Kowalczyk、Markwart Kunz、Manfred Vogel

  DOI：10.1055/s-2003-38075

  日期：——

  forming β1→4 linkages. The synthesis of several biologically relevant tri- and tetrasaccharides β-D-Galp-(1→4)-β-D-Galp-(1→4)-α,β-D-Glcp (2), β-D-Galp-(1→4)-α-D-Glcp-(1→4)-D-Glcp-ol/Manp-ol (4), β-D-Galp-(1→4)-α-D-Glcp-(1→6)-β-D-Fruf (6), β-D-Galp-(1→4)-α-D-Glcp-(1↔2)-β-D-Fruf (8), β-D-Galp-(1→4)-α-D-Glcp-(1↔2)-β-D-Fruf-(1↔2)-β-D-Fruf (10), β-D-Galp-(1→4)-α-D-Glcp-(1→6)-[α-D-Glcp-(1↔2)]-β-D-Fruf (12a)

  来自环状芽孢杆菌的 β-半乳糖苷酶 (EC 3.2.1.23) 催化半乳糖单位向各种葡萄糖和半乳糖衍生物的转移，形成 β1→4 键。几种生物学相关的三糖和四糖的合成β-D-Galp-(1→4)-β-D-Galp-(1→4)-α,β-D-Glcp (2), β-D- Galp-(1→4)-α-D-Glcp-(1→4)-D-Glcp-ol/Manp-ol(4)、β-D-Galp-(1→4)-α-D-Glcp -(1→6)-β-D-Fruf (6), β-D-Galp-(1→4)-α-D-Glcp-(1↔2)-β-D-Fruf (8), β -D-Galp-(1→4)-α-D-Glcp-(1↔2)-β-D-Fruf-(1↔2)-β-D-Fruf (10), β-D-Galp- (1→4)-α-D-Glcp-(1→6)-[α-D-Glcp-(1↔2)]-β-D-Fruf (12a), β-D-Galp-(1→