5^A-carboxy-5^A-dehydroxymethyl-2^A,2^B,2^C,2^D,2^E,2^F,2^G,3^A,3^B,3^C,3^D,3^E,3^F,3^G,6^B,6^C,6^D,6^E,6^F,6^G-icosa-O-methyl-β-cyclodextrin | 148259-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5^A-carboxy-5^A-dehydroxymethyl-2^A,2^B,2^C,2^D,2^E,2^F,2^G,3^A,3^B,3^C,3^D,3^E,3^F,3^G,6^B,6^C,6^D,6^E,6^F,6^G-icosa-O-methyl-β-cyclodextrin
• 英文别名: 6^I-desoxy-6^I-carboxy-2^{I-VII_,3I-VII_,6II-VII}-eicosa-O-methyl-cyclomaltoheptaose；(1R,3R,5R,6R,8R,10R,11R,13S,15S,16S,18R,20R,21R,23R,25R,26R,28R,30R,31R,33R,35R,36S,37R,38S,39R,40S,41R,42S,43R,44S,45R,46S,47R,48S,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecamethoxy-5,10,20,25,30,35-hexakis(methoxymethyl)-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-15-carboxylic acid
• CAS: 148259-75-0
• 化学式: C₆₂H₁₀₈O₃₆
• 分子量: 1429.52
• InChiKey: GICIOLWTFYMTHX-WSMPWQNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  98
• 可旋转键数：
  27
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  351
• 氢给体数：
  1
• 氢受体数：
  36

反应信息

• 作为反应物：
  描述：

  5^A-carboxy-5^A-dehydroxymethyl-2^A,2^B,2^C,2^D,2^E,2^F,2^G,3^A,3^B,3^C,3^D,3^E,3^F,3^G,6^B,6^C,6^D,6^E,6^F,6^G-icosa-O-methyl-β-cyclodextrin 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 5^A-chloroformyl-5^A-dehydroxymethyl-2^A,2^B,2^C,2^D,2^E,2^F,2^G,3^A,3^B,3^C,3^D,3^E,3^F,3^G,6^B,6^C,6^D,6^E,6^F,6^G-icosa-O-methyl-β-cyclodextrin
  参考文献：
  名称：

  Heptakis(2,3,6-tri-O-methyl)-β-环糊精衍生物改性氨基丙基硅胶液相色谱

  摘要：

  制备了由七（2,3,6-O-三甲基）-β-环糊精改性的新固定相，并作为 HPLC 柱进行了测试。结果表明，这些固定相在反相条件下对各种类型的芳香族化合物表现出显着的手性分离能力。硅胶上残留氨基的乙酰化和丙酰化提高了固定相的保留能力，并导致更好的色谱手性分离。对于酰化固定相观察到的这种优异手性分离的最可能原因之一被认为是固定相疏水表面上溶质的局部浓度增加，这增加了溶质与外部接触的可能性。环糊精固定在硅胶上。

  DOI：

  10.1246/bcsj.66.1116
• 作为产物：
  描述：

  permethylated mono-6-hydroxy-β-cyclodextrin 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 作用下， 生成 5^A-carboxy-5^A-dehydroxymethyl-2^A,2^B,2^C,2^D,2^E,2^F,2^G,3^A,3^B,3^C,3^D,3^E,3^F,3^G,6^B,6^C,6^D,6^E,6^F,6^G-icosa-O-methyl-β-cyclodextrin
  参考文献：
  名称：

  Selective access and full characterization of mono-acidic permethylated β-cyclodextrin derivatives and their methyl esters

  摘要：

  Three acidic derivatives of permethylated beta-cyclodextrin, 2(I)-O-carboxymethyl-2(II-VII),3(I-VII),6(I-VII)-eicosa-O-methyl-cyclomaltoheptaose, 6(I)-O-carboxymethyl-2(I-VII),3(I-VII),6(II-VII)-eicosa-O-methyl-cyclomaltoheptaose, 6(I)-desoxy-6(I)-carboxy-2(I-VII),3(I-III),6(II-VII)-eicosa-O-methyl-cyclomaltoheptaose and the corresponding methyl esters have been synthesized with good yields starting from mono-hydroxy permethylated beta-CD prepared via tert-butyldimethylsilyl protection in 6-position and p-methoxybenzyl protection at the 2-position. All of these compounds were fully characterized by high field H-1 and C-13 NMR and HPLC/MS. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00446-4

文献信息

• Substantial Spatial Flexibility and Hydrogen Bonding within the Catalysis Exerted by Cyclodextrin Artificial Glycosidases
  作者：Jeannette Bjerre、Mikael Bols

  DOI：10.1002/ejoc.201000380

  日期：——

  Herein we report the synthesis of a novel 7 A ,7 D -dicyanohydrin-β-cyclodextrin that catalyzes the hydrolysis of aryl glycosides with up to 5500 times rate increase (k cat /k uncat ), functioning as a glycosidase enzyme mimic. For all glycoside substrates tested at 50 mM phosphate buffer this catalysis is superior to previously reported results for 6 A ,6 D -dicyanohydrin cyclodextrin (CD) artificial glycosidases

  在本文中，我们报告了一种新型 7 A ,7 D -二氰醇-β-环糊精的合成，它以高达 5500 倍的速率增加（k cat /k uncat ）催化芳基糖苷的水解，起到糖苷酶模拟物的作用。对于在 50 mM 磷酸盐缓冲液中测试的所有糖苷底物，这种催化作用优于先前报道的 6 A,6 D-二氰醇环糊精 (CD) 人工糖苷酶的结果，即催化基团靠近环糊精空腔的一个碳原子的类似物。这证明了这些 CD 化学酶发挥的催化作用具有很大的灵活性。还合成了一系列全甲基化的单氰醇和二氰醇 α- 和 β-CD，这些催化速率提高了 110 倍（催化速率为 10%，相对于非甲基化类似物），这意味着全甲基化阻断或阻碍了底物的糖类部分与 CD 之间具有催化作用的重要结合。为了进行比较，还合成了全甲基化 6 A,6 D-二羧酸 β-CD，相对于非全甲基化 6 A,6 D-二羧酸 β-CD，其活性提高了 25%（速率增加了 250
• Selective access and full characterization of mono-acidic permethylated β-cyclodextrin derivatives and their methyl esters
  作者：S. Tisse、V. Peulon-Agasse、H. Oulyadi、F. Marsais、J.C. Combret

  DOI：10.1016/s0957-4166(03)00446-4

  日期：2003.8

  Three acidic derivatives of permethylated beta-cyclodextrin, 2(I)-O-carboxymethyl-2(II-VII),3(I-VII),6(I-VII)-eicosa-O-methyl-cyclomaltoheptaose, 6(I)-O-carboxymethyl-2(I-VII),3(I-VII),6(II-VII)-eicosa-O-methyl-cyclomaltoheptaose, 6(I)-desoxy-6(I)-carboxy-2(I-VII),3(I-III),6(II-VII)-eicosa-O-methyl-cyclomaltoheptaose and the corresponding methyl esters have been synthesized with good yields starting from mono-hydroxy permethylated beta-CD prepared via tert-butyldimethylsilyl protection in 6-position and p-methoxybenzyl protection at the 2-position. All of these compounds were fully characterized by high field H-1 and C-13 NMR and HPLC/MS. (C) 2003 Elsevier Ltd. All rights reserved.
• Liquid Chromatography with Aminopropylsilica Gel Modified by Heptakis(2,3,6-tri-<i>O</i>-methyl)-<i>β</i>-cyclodextrin Derivative
  作者：Yasuhisa Kuroda、Teru Kato、Hisanobu Ogoshi

  DOI：10.1246/bcsj.66.1116

  日期：1993.4

  New stationary phases modified by heptakis(2,3,6-O-trimethyl)-β-cyclodextrin were prepared and tested as HPLC columns. The results show that these stationary phases exhibit significant chiral separation abilities for various types of aromatic compounds under reversed-phase conditions. Acetylation and propionylation of the residual amino groups on silica gel improve the retention capacity of the stationary

  制备了由七（2,3,6-O-三甲基）-β-环糊精改性的新固定相，并作为 HPLC 柱进行了测试。结果表明，这些固定相在反相条件下对各种类型的芳香族化合物表现出显着的手性分离能力。硅胶上残留氨基的乙酰化和丙酰化提高了固定相的保留能力，并导致更好的色谱手性分离。对于酰化固定相观察到的这种优异手性分离的最可能原因之一被认为是固定相疏水表面上溶质的局部浓度增加，这增加了溶质与外部接触的可能性。环糊精固定在硅胶上。