(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-(2-氯-4-硝基苯氧基)-4,5-二羟基-2-(羟基甲基)四氢吡喃-3-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇 | 143206-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-(2-氯-4-硝基苯氧基)-4,5-二羟基-2-(羟基甲基)四氢吡喃-3-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
• 中文别名: 2,2-二氯-N-{[5-(甲氧基甲基)呋喃-2-基]甲基}-N-甲基乙酰胺
• 英文名称: 2-chloro-4-nitrophenyl β-maltoside
• 英文别名: 2-Chloro-4-nitrophenylmaltoside；(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-(2-chloro-4-nitrophenoxy)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 143206-27-3
• 化学式: C₁₈H₂₄ClNO₁₃
• 分子量: 497.84
• InChiKey: RFGBZYLCQCJGOG-YMJSIHPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  224
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-(2-氯-4-硝基苯氧基)-4,5-二羟基-2-(羟基甲基)四氢吡喃-3-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇 、 4,6-O-3-ketobutylidene β-maltopentaoside 以 丙醇 、 水 为溶剂， 反应 10.0h， 以21%的产率得到2-chloro-4-nitrophenyl 4,6-O-3-ketobutylidene β-maltohexaoside
  参考文献：
  名称：

  Enzymatic Synthesis of 2-Chloro-4-nitrophenyl 4,6-O-3-Ketobutylideneβ-Maltopentaoside, a Substrate forα-Amylase

  摘要：

  在含有50%正丙醇的水溶液中，以2-氯-4-硝基苯基β-麦芽糖苷为受体，用4,6-O-3-酮基丁烯基麦芽五糖和Bacillus macerans环糊精葡糖基转移酶进行了转糖基化反应，并得到了两种主要的转糖基化产物。它们被鉴定为2-氯-4-硝基苯基4,6-O-3-酮基丁烯基β-麦芽五糖苷和2-氯-4-硝基苯基4,6-O-3-酮基丁烯基β-麦芽六糖苷，根据4,6-O-3-酮基丁烯基麦芽五糖的减少量，它们的产量分别为30%和21%。在高底物浓度下生产2-氯-4-硝基苯基4,6-O-3-酮基丁烯基β-麦芽五糖苷时，在该反应中添加正丙醇不仅能够充分增加2-氯-4-硝基苯基β-麦芽糖苷的溶解度，还能抑制副反应。

  DOI：

  10.1271/bbb.56.1552
• 作为产物：
  描述：

  2-氯-4-硝基苯基-麦芽五糖苷 在 human salivary α-amylase 、 sodium chloride 、 calcium chloride 作用下， 以 phosphate buffer 为溶剂， 生成 (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-(2-氯-4-硝基苯氧基)-4,5-二羟基-2-(羟基甲基)四氢吡喃-3-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇 、 2-氯-4-硝基苯基-beta-D-葡糖-吡喃糖苷 、 2-氯-4-硝基苯基-β-D-麦芽三糖糖苷
  参考文献：
  名称：

  Examination of the active sites of human salivary α-amylase (HSA)

  摘要：

  The action pattern of human salivary amylase (HSA) was examined by utilising as model substrates 2-chloro-4-nitrophenyl (CNP) beta -glycosides of maltooligosaccharides of dp 4-8 and some 4-nitrophenyl (NP) derivatives modified at the nonreducing end with a 4,6-O-benzylidene (Bnl) group. The product pattern and cleavage frequency were investigated by product analysis using HPLC. The results revealed that the binding region in HSA is longer than five subsites usually considered in the literature and suggested the presence of at least six subsites; four glycone binding sites (- 4, - 3, - 2, - 1) and two aglycone binding sites (+ 1, + 2). In the ideal arrangement, the six subsites are filled by a glucosyl unit and the release of maltotetraose (G(4)) from the nonreducing end is dominant. The benzylidene group was also recognisable by subsites (- 3) and ( - 4). The binding modes of the benzylidene derivatives indicated a favourable interaction between the Bnl group and subsite (- 3) and an unfavourable one with subsite (- 4). Thus, subsite (- 4) must be more hydrophylic than hydrophobic. As compared with the action of porcine pancreatic alpha -amylase (PPA) on the same substrates, the results showed differences in the three-dimensional structure of active sites of HSA and PPA. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00221-4

文献信息

• Examination of the active sites of human salivary α-amylase (HSA)
  作者：Lili Kandra、Gyöngyi Gyémánt

  DOI：10.1016/s0008-6215(00)00221-4

  日期：2000.11

  The action pattern of human salivary amylase (HSA) was examined by utilising as model substrates 2-chloro-4-nitrophenyl (CNP) beta -glycosides of maltooligosaccharides of dp 4-8 and some 4-nitrophenyl (NP) derivatives modified at the nonreducing end with a 4,6-O-benzylidene (Bnl) group. The product pattern and cleavage frequency were investigated by product analysis using HPLC. The results revealed that the binding region in HSA is longer than five subsites usually considered in the literature and suggested the presence of at least six subsites; four glycone binding sites (- 4, - 3, - 2, - 1) and two aglycone binding sites (+ 1, + 2). In the ideal arrangement, the six subsites are filled by a glucosyl unit and the release of maltotetraose (G(4)) from the nonreducing end is dominant. The benzylidene group was also recognisable by subsites (- 3) and ( - 4). The binding modes of the benzylidene derivatives indicated a favourable interaction between the Bnl group and subsite (- 3) and an unfavourable one with subsite (- 4). Thus, subsite (- 4) must be more hydrophylic than hydrophobic. As compared with the action of porcine pancreatic alpha -amylase (PPA) on the same substrates, the results showed differences in the three-dimensional structure of active sites of HSA and PPA. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Enzymatic Synthesis of 2-Chloro-4-nitrophenyl 4,6-<i>O</i>-3-Ketobutylidene<i>β</i>-Maltopentaoside, a Substrate for<i>α</i>-Amylase
  作者：Katsutoshi Ishimaru、Yoshikazu Kamezono、Shinichi Teshima、Yuzo Hayashi

  DOI：10.1271/bbb.56.1552

  日期：1992.1

  A transglycosylation reaction with 2-chloro-4-nitrophenyl β-maltoside as an acceptor was done with 4,6-O-3-ketobutylidene maltopentaose and Bacillus macerans cyclodextrin glucanotransferase in an aqueous solution containing 50% n-propanol, and there were two main transglycosylation products. They were identified as 2-chloro-4-nitrophenyl 4,6-O-3-ketobutylidene β-maltopentaoside and 2-chloro-4-nitrophenyl 4,6-O-3-ketobutylidene β-maltohexaoside, and their yields were 30% and 21%, respectively on the basis of the decrease of 4,6-O-3-ketobutylidene maltopentaose. For the production of 2-chloro-4-nitrophenyl 4,6-O-3-ketobutylidene β-maltopentaoside at high substrates concentrations, the addition of n-propanol in this reaction not only increased the solubility of 2-chloro-4-nitrophenyl β-maltoside sufficiently but also suppressed side reactions.

  在含有50%正丙醇的水溶液中，以2-氯-4-硝基苯基β-麦芽糖苷为受体，用4,6-O-3-酮基丁烯基麦芽五糖和Bacillus macerans环糊精葡糖基转移酶进行了转糖基化反应，并得到了两种主要的转糖基化产物。它们被鉴定为2-氯-4-硝基苯基4,6-O-3-酮基丁烯基β-麦芽五糖苷和2-氯-4-硝基苯基4,6-O-3-酮基丁烯基β-麦芽六糖苷，根据4,6-O-3-酮基丁烯基麦芽五糖的减少量，它们的产量分别为30%和21%。在高底物浓度下生产2-氯-4-硝基苯基4,6-O-3-酮基丁烯基β-麦芽五糖苷时，在该反应中添加正丙醇不仅能够充分增加2-氯-4-硝基苯基β-麦芽糖苷的溶解度，还能抑制副反应。