2-chloro-4-nitrophenyl O-<4,6-O-(1,1-dimethoxy)methylidene-α-D-glucopyranosyl>-(1->4)-tris4)>-β-D-glucopyranoside | 147234-15-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloro-4-nitrophenyl O-<4,6-O-(1,1-dimethoxy)methylidene-α-D-glucopyranosyl>-(1->4)-tris4)>-β-D-glucopyranoside
• CAS: 147234-15-9
• 化学式: C₃₉H₅₈ClNO₃₀
• 分子量: 1056.33
• InChiKey: UYZCHMPQMSUELJ-XQRRXTBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.31
• 重原子数：
  71.0
• 可旋转键数：
  17.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  455.58
• 氢给体数：
  14.0
• 氢受体数：
  30.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-chloro-4-nitrophenyl O-<4,6-O-(1,1-dimethoxy)methylidene-α-D-glucopyranosyl>-(1->4)-tris4)>-β-D-glucopyranoside 在 吡啶 作用下， 生成
  参考文献：
  名称：

  Syntheses of modified 2-chloro-4-nitrophenyl β-maltopentaosides as useful substrates for assay of human alpha amylase

  摘要：

  Twenty-three novel 2-chloro-4-nitrophenyl beta-D-maltopentaosides modified at the 6(5) and/or 4(5) position were synthesized as substrates for human alpha amylase. Two human alpha amylases hydrolyzed 6(5)-deoxy-6(5)-, 6(5)-O-, and 4(5),6(5)-di-O-substituted derivatives at essentially a single D-glucosidic linkage, but 4(5),6(5)-O-bridged and 4(5)-O-substituted derivatives were hydrolyzed at two or more linkages. The amylases displayed smaller K(m) values for the compounds having hydrophobic modifications. In these derivatives, 2-chloro-4-nitrophenyl O-(6-bromo-6-deoxy-alpha-D-glucopyranosyl)-(1 --> 4)-tris[O-alpha-D-glucopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (10), 2-chloro-4-nitrophenyl O-(6-azido-6-deoxy-alpha-D-gluco-pyranosyl)-(1 --> 4)-tris[O-alpha-D-glucopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (19), and 2-chloro-4-nitrophenyl O-[6-O-(N-isopropyl)carbamoyl-alpha-D-glucopyranosyl]-(1 --> 4)-tris[O-alpha-D-glucopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (30), which were rapidly hydrolyzed by the two amylases at a limited position at an approximately equal rate, were shown to be very useful blocked-type substrates for assay of human alpha amylase.

  DOI：

  10.1016/0008-6215(93)87008-g
• 作为产物：
  描述：

  原碳酸四甲酯 、 2-氯-4-硝基苯基-麦芽五糖苷 在 Amberlyst 15E 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以66.5%的产率得到2-chloro-4-nitrophenyl O-<4,6-O-(1,1-dimethoxy)methylidene-α-D-glucopyranosyl>-(1->4)-tris4)>-β-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of modified 2-chloro-4-nitrophenyl β-maltopentaosides as useful substrates for assay of human alpha amylase

  摘要：

  Twenty-three novel 2-chloro-4-nitrophenyl beta-D-maltopentaosides modified at the 6(5) and/or 4(5) position were synthesized as substrates for human alpha amylase. Two human alpha amylases hydrolyzed 6(5)-deoxy-6(5)-, 6(5)-O-, and 4(5),6(5)-di-O-substituted derivatives at essentially a single D-glucosidic linkage, but 4(5),6(5)-O-bridged and 4(5)-O-substituted derivatives were hydrolyzed at two or more linkages. The amylases displayed smaller K(m) values for the compounds having hydrophobic modifications. In these derivatives, 2-chloro-4-nitrophenyl O-(6-bromo-6-deoxy-alpha-D-glucopyranosyl)-(1 --> 4)-tris[O-alpha-D-glucopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (10), 2-chloro-4-nitrophenyl O-(6-azido-6-deoxy-alpha-D-gluco-pyranosyl)-(1 --> 4)-tris[O-alpha-D-glucopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (19), and 2-chloro-4-nitrophenyl O-[6-O-(N-isopropyl)carbamoyl-alpha-D-glucopyranosyl]-(1 --> 4)-tris[O-alpha-D-glucopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (30), which were rapidly hydrolyzed by the two amylases at a limited position at an approximately equal rate, were shown to be very useful blocked-type substrates for assay of human alpha amylase.

  DOI：

  10.1016/0008-6215(93)87008-g