5^A,5^D-dicarboxy-β-cyclodextrin | 126628-31-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5^A,5^D-dicarboxy-β-cyclodextrin
• 英文别名: A,D-Dicarboxy-β-cyclodextrin；(1S,3S,5S,6S,8R,10R,11S,13R,15R,16S,18S,20S,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,25,30,35-pentakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-5,20-dicarboxylic acid
• CAS: 126628-31-7
• 化学式: C₄₂H₆₆O₃₇
• 分子量: 1162.96
• InChiKey: TZCMCNZRZPJCQA-QRSDJFHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -14.5
• 重原子数：
  79
• 可旋转键数：
  7
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  588
• 氢给体数：
  21
• 氢受体数：
  37

反应信息

• 作为反应物：
  描述：

  5^A,5^D-dicarboxy-β-cyclodextrin 生成 A,D-dicarboxyl of 2,3,6-permethyl-β-cyclodextrin
  参考文献：
  名称：

  KURODA, YASUHISA;KOBAYASHI, OSAMU;SUZUKI, YASUHIKO;OGOSHI, HISANOBU, TETRAHEDRON LETT., 30,(1989) N1, C. 7225-7228

  摘要：

  DOI：
• 作为产物：
  描述：

  nonadeca-O-benzyl-β-cyclodextrin-6^A,6^D-dicarboxylic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以100%的产率得到5^A,5^D-dicarboxy-β-cyclodextrin
  参考文献：
  名称：

  催化芳基糖苷水解的人工酶

  摘要：

  合成了两种环糊精A，D-二酸，发现其催化的k cat / k uncat高达35的硝基苯基糖苷的水解。水解遵循Michaelis-Menten动力学，可被结合腔的化合物抑制，最佳发生于pH值7.4。

  DOI：

  10.1016/j.tetlet.2004.09.134

文献信息

• Artificial Metallooxidases from Cyclodextrin Diacids
  作者：Bo Wang、Mikael Bols

  DOI：10.1002/chem.201702530

  日期：2017.10.4

  Creating catalysts: Iron cyclodextrin complexes have been constructed as artificial oxidases of benzyl ethers (see scheme). The iron complexes were found to catalyse a Fenton-like oxidation reaction of benzylic alcohols, which displayed Michaelis–Menten catalysis and rate accelerations up to 2700.

  产生催化剂：环糊精铁络合物已被构造为苄基醚的人工氧化酶（参见方案）。发现铁络合物催化苄醇的Fenton样氧化反应，显示出Michaelis–Menten催化作用，速率加速至2700。
• Selective oxidation of primary alcohol groups of β-cyclodextrin mediated by 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO)
  作者：Carole Fraschini、Michel R. Vignon

  DOI：10.1016/s0008-6215(00)00129-4

  日期：2000.10

  Beta-cyclodextrin (beta-CD) was reacted with catalytic amounts of 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO), sodium hypochlorite and sodium bromide at 2 degrees C and a pH value of 10 in water. The primary alcohol groups were selectively oxidized into carboxylate groups within a few minutes, and mono- and dicarboxy-beta-cyclodextrin sodium salts were isolated and characterized by 1H, 13C

  在2摄氏度和pH值为10的水中，将β-环糊精（β-CD）与催化量的2,2,6,6-四甲基哌啶-1-氧基（TEMPO），次氯酸钠和溴化钠反应。在几分钟内将伯醇基团选择性地氧化成羧酸根基团，并分离出单羧基和二羧基-β-环糊精钠盐，并通过1H，13C NMR和质谱进行了表征。通过该反应系统，环氧化糊精的降解受到限制，条件是该氧化反应需在2摄氏度，恒定pH值为10的条件下进行，并使用催化量的TEMPO和受控量的次氯酸钠和溴化钠进行连续再生。氧铵盐。
• A General Method for the Synthesis of Cyclodextrinyl Aldehydes and Carboxylic Acids
  作者：Juyoung Yoon、Sungyeap Hong、Kristy A. Martin、Anthony W. Czarnik

  DOI：10.1021/jo00114a030

  日期：1995.5

  The selective synthesis of the primary-side monoaldehyde of beta-cyclodextrin, 6-deoxy-6-formyl-beta-cyclodextrin, was accomplished by oxidation of the corresponding tosylate utilizing the Nace reaction (DMSO/collidine). This monoaldehyde was then used as the starting material in several reactions including reduction, addition of NaHSO3, addition of the alpha-nucleophiles hydroxylamine and hydrazine, and reductive amination. Of particular interest is the conversion of the monoaldehyde to the primary side carboxylic acid, 6-deoxy-6-carboxy-beta-cyclodextrin, via bromine oxidation. This general method sequence can be applied to any tosyl derivative of cyclodextrin as demonstrated in the synthesis of beta-cyclodextrin-A,D-dialdehyde and beta-cyclodextrin-A,D-diacid.
• 5A,5D-dicarboxy-β-cyclodextrin derivatives - a route for regioselectively difunctionalized permethyl-β-cyclodextrin
  作者：Yasuhisa Kuroda、Osamu Kobayashi、Yasuhiko Suzuki、Hisanobu Ogoshi

  DOI：10.1016/s0040-4039(01)93941-3

  日期：1989.1
• An artificial enzyme that catalyzes hydrolysis of aryl glycosides
  作者：Cyril Rousseau、Naja Nielsen、Mikael Bols

  DOI：10.1016/j.tetlet.2004.09.134

  日期：2004.11

  Two cyclodextrin A,D-diacids were synthesized and found to catalyze the hydrolysis of nitrophenyl glycosides with kcat/kuncat of up to 35. The hydrolysis followed Michaelis–Menten kinetics, could be inhibited by compounds binding the cavity, and occurred optimally at pH 7.4.

  合成了两种环糊精A，D-二酸，发现其催化的k cat / k uncat高达35的硝基苯基糖苷的水解。水解遵循Michaelis-Menten动力学，可被结合腔的化合物抑制，最佳发生于pH值7.4。