O-(6-deoxy-α-D-glucopyranosyl)-(1->4)-O-(α-D-glucopyranosyl)-(1->4)-D-glucopyranose | 86462-09-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(6-deoxy-α-D-glucopyranosyl)-(1->4)-O-(α-D-glucopyranosyl)-(1->4)-D-glucopyranose
• 英文别名: 6(3)-Deoxymaltotriose；(2R,3R,4S,5S,6R)-2-[(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-6-methyloxane-3,4,5-triol
• CAS: 86462-09-1；86462-10-4；86462-14-8；86462-15-9
• 化学式: C₁₈H₃₂O₁₅
• 分子量: 488.443
• InChiKey: VRSXSNOOHWJZDV-DZOUCCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  248
• 氢给体数：
  10
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  麦芽糖 在 palladium on activated charcoal sodium hydroxide 、 cyclodextrin glycosyltransferase 、 human salivary amylase 、 PIPES buffer 、 氢气 、 sodium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 O-(6-deoxy-α-D-glucopyranosyl)-(1->4)-O-(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

• Syntheses of subtractively modified 2-chloro-4-nitrophenyl β-maltopentaosides and their application to the differential assay of human alpha-amylases
  作者：Shoichi Tokutake、Tetsuya Oguma、Kouichirou Tobe、Kazuo Kotani、Kazunori Saito、Nobuyuki Yamaji

  DOI：10.1016/0008-6215(93)87013-i

  日期：1993.1

  Three novel maltopentaosides, 2-chloro-4-nitrophenyl O-(6-deoxy-alpha-D-xylo-hex-5-enopyranosyl)-(1 --> 4)-tris[O-alpha-D-glucopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (3), 2-chloro-4-nitrophenyl O-(6-deoxy-alpha-D-glucopyranosyl)-(1 --> 4)-tris[O-alpha-D-glucopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (10), and 2-chloro-4-nitrophenyl O-(3,6-anhydro-alpha-D-glucopyranosyl)-(1 --> 4)-tris[O-alpha-D-glucopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (26) were synthesized by chemical and enzymatic reactions. Two human alpha-amylases, salivary alpha-amylase (HSA) and pancreatic alpha-amylase (HPA), hydrolyzed 3 and 10 with the same specificity, almost entirely at a single D-glucosidic linkage, but had no hydrolytic acitivity for 26. Compound 3 was hydrolyzed by each of these amylases at an approximately equal rate, while 10 was hydrolyzed by HSA 4-fold faster than by HPA. Taking advantage of the difference in the hydrolytic rate of 10, we developed a new method for the differential assay of these two human alpha-amylases.
• 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.