α-D-glucopyranosyl-(1->4)-(6-O-p-toluenesulfonyl-α-D-glucopyranosyl)-(1->4)-α-D-glucopyranosyl-(1->4)-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-glucopyranosyl-(1->4)-(6-O-p-toluenesulfonyl-α-D-glucopyranosyl)-(1->4)-α-D-glucopyranosyl-(1->4)-D-glucopyranose
• 英文别名: Glc(a1-4)[Tos(-6)]Glc(a1-4)Glc(a1-4)Glc；[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• 化学式: C₃₁H₄₈O₂₃S
• 分子量: 820.774
• InChiKey: LRSYVOCBXCWNTF-YINKDGGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7
• 重原子数：
  55
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  379
• 氢给体数：
  13
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  α-D-glucopyranosyl-(1->4)-(6-O-p-toluenesulfonyl-α-D-glucopyranosyl)-(1->4)-α-D-glucopyranosyl-(1->4)-D-glucopyranose 在 barium dihydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 以93.5%的产率得到3",6"-anhydromaltotetraose
  参考文献：
  名称：

  Enzymatic Synthesis of Specifically Modified Linear Oligosaccharides from γ-Cyclodextrin Derivatives. Study on Importance of Active Sites of Taka Amylase A

  摘要：

  特定修改的线性寡糖是通过Taka淀粉酶A对6-或2-O取代的γ-环糊精进行酶解得到的。这些结果表明，羟基之间的相互作用以及与Taka淀粉酶A的亚位点（P–V）的重要性按以下顺序递减；对于C-6-OH，顺序为S>R>T>Q，U；对于C-2-OH，顺序为R,S>T>Q，U。

  DOI：

  10.1246/bcsj.62.3150
• 作为产物：
  描述：

  单-6-O-(对甲苯磺酰)-γ-环糊精 在 acetate buffer 、 Taka amylase A 、 calcium chloride 作用下， 以 水 为溶剂， 反应 2.0h， 以31.6%的产率得到α-D-glucopyranosyl-(1->4)-(6-O-p-toluenesulfonyl-α-D-glucopyranosyl)-(1->4)-α-D-glucopyranosyl-(1->4)-D-glucopyranose
  参考文献：
  名称：

  Enzymatic Synthesis of Specifically Modified Linear Oligosaccharides from γ-Cyclodextrin Derivatives. Study on Importance of Active Sites of Taka Amylase A

  摘要：

  特定修改的线性寡糖是通过Taka淀粉酶A对6-或2-O取代的γ-环糊精进行酶解得到的。这些结果表明，羟基之间的相互作用以及与Taka淀粉酶A的亚位点（P–V）的重要性按以下顺序递减；对于C-6-OH，顺序为S>R>T>Q，U；对于C-2-OH，顺序为R,S>T>Q，U。

  DOI：

  10.1246/bcsj.62.3150

文献信息

• New enzymatic synthesis of 63-modified maltooligosaccharides and their inhibitory activities for human α-amylases
  作者：Riichiro Uchida、Ayako Nasu、Shoichi Tokutake、Kouichi Kasai、Koichiro Tobe、Nobuyuki Yamaji

  DOI：10.1016/s0008-6215(98)00029-9

  日期：1998.2

  Ten new 6(3)-modified maltopentaoses and tetraoses were synthesized by enzymatic reactions utilizing cyclodextrin glycosyltransferase (EC 2.4.1.19) and subsequent human salivary alpha-amylase (HSA) (EC 3.2.1.1). Among these compounds, alpha-D-glucopyranosyl-(1-->4)-alpha-D-glucopyranosyl-(1 -->4)-(6-deoxy-alpha-D-glucopyranosyl)-(1-->4)-alpha-D-glucopyranosyl-(1-->4)-D-glucopyranose (11) and alpha-D-glucopyranosyl-(1--->4)-(6-deoxy-alpha-D-glucopyranosyl)-(1-->4)-alpha-D-glucopyranosyl-(1-->4)-D-glucopyranose (12) showed strong inhibitory activities for human pancreatic alpha-amylase (HPA) and HSA. The IC50 Of 6(3)-deoxymaltopentaose 11 (8.0x10(-5)M for HPA, 1.0x10(-4)M for HSA) and 6(3)-deoxymaltotetraose 12 (2.0x10(-3)M for HPA, 2.0x10(-3)M for HSA) were lower than that of 6(3)-deoxymaltotriose [(6-deoxy-alpha-D-glucopyranosyl)-(1-->4)-alpha-D-glucopyranosyl-(1-->4)-D-glucopyranose 13; 2.0x10-3M for HPA, 4.2x10(-2)M for HSA]. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Enzymatic Synthesis of Specifically Modified Linear Oligosaccharides from γ-Cyclodextrin Derivatives. Study on Importance of Active Sites of Taka Amylase A
  作者：Kahee Fujita、Tsutomu Tahara、Toshitaka Koga、Taiji Imoto

  DOI：10.1246/bcsj.62.3150

  日期：1989.10

  Specifically modified linear oligosaccharides were prepared by enzymatic hydrolysis of 6- or 2-O-substituted γ-cyclodextrin by Taka amylase A. These results suggest that the importance of the interactions between hydroxyl groups and the subsites (P–V) of Taka amylase A decreases in the following order; for C-6-OH, S>R>T>Q, U and for C-2-OH, R,S>T>Q, U.

  特定修改的线性寡糖是通过Taka淀粉酶A对6-或2-O取代的γ-环糊精进行酶解得到的。这些结果表明，羟基之间的相互作用以及与Taka淀粉酶A的亚位点（P–V）的重要性按以下顺序递减；对于C-6-OH，顺序为S>R>T>Q，U；对于C-2-OH，顺序为R,S>T>Q，U。