α-D-glucopyranosyl-(1->4)-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)-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)Glc(a1-4)[Tos(-6)]Glc(a1-4)Glc(a1-4)Glc；[(2R,3S,4R,5R,6R)-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-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-dihydroxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• 化学式: C₃₇H₅₈O₂₈S
• 分子量: 982.917
• InChiKey: VZXGGGUZAAVSFX-PBYIVTHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.1
• 重原子数：
  66
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  459
• 氢给体数：
  16
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  α-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl-(1->4)-(6-O-p-toluenesulfonyl-α-D-glucopyranosyl)-(1->4)-α-D-glucopyranosyl-(1->4)-D-glucopyranose 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以79%的产率得到α-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl-(1->4)-(6-deoxy-6-iodo-α-D-glucopyranosyl)-(1->4)-α-D-glucopyranosyl-(1->4)-D-glucopyranose
  参考文献：
  名称：

  New enzymatic synthesis of 63-modified maltooligosaccharides and their inhibitory activities for human α-amylases

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(98)00029-9
• 作为产物：
  描述：

  麦芽糖 、 单-6-O-(对甲苯磺酰)-α-环糊精 在 sodium hydroxide 、 cyclodextrin glycosyltransferase 、 human salivary amylase 、 PIPES buffer 作用下， 生成 6''-O-(p-tosyl)maltotriose 、 α-D-glucopyranosyl-(1->4)-(6-O-p-toluenesulfonyl-α-D-glucopyranosyl)-(1->4)-α-D-glucopyranosyl-(1->4)-D-glucopyranose 、 α-D-glucopyranosyl-(1->4)-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：

  New enzymatic synthesis of 63-modified maltooligosaccharides and their inhibitory activities for human α-amylases

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(98)00029-9

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.