Mono-3^A,6^A-anhydrocyclomaltoheptaose | 104867-20-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Mono-3^A,6^A-anhydrocyclomaltoheptaose
• 英文别名: 3^A,6^A-anhydro-β-cyclodextrin；mono-(3,6-di-O-anhydro)-β-cyclodextrin；3A,6A-anhydro-β-cyclodextrin；3,6-anhydro-β-cyclodextrin；3,6-anhydrocyclomaltoheptaose；AβCD；(1R,3R,4R,7R,9R,11S,12R,14R,16S,17R,19R,21S,22R,24R,26S,27R,29R,31S,32R,34R,36S,37R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R,50R,51R)-12,17,22,27,32,37-hexakis(hydroxymethyl)-2,5,8,10,13,15,18,20,23,25,28,30,33,35,38-pentadecaoxanonacyclo[34.2.2.211,14.216,19.221,24.226,29.231,34.14,9.03,7]henpentacontane-39,40,41,42,43,44,45,46,47,48,49,50,51-tridecol
• CAS: 104867-20-1
• 化学式: C₄₂H₆₈O₃₄
• 分子量: 1116.98
• InChiKey: UJSIFVFKFITSHK-FOUAGVGXSA-N

物化性质

• 密度：
  1.617±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -14
• 重原子数：
  76
• 可旋转键数：
  6
• 环数：
  22.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  523
• 氢给体数：
  19
• 氢受体数：
  34

反应信息

• 作为反应物：
  描述：

  Mono-3^A,6^A-anhydrocyclomaltoheptaose 在 Taka amylase acetate buffer 、 calcium chloride 作用下， 反应 72.0h， 以85.4%的产率得到3",6"-anhydromaltotetraose
  参考文献：
  名称：

  Preparation of 3^A,6^A-Anhydro-β-cyclodextrin and Its Taka Amylolysis

  摘要：

  3A,6A-脱水-β-环糊精是由 6-O-（对甲苯磺酰基）-β-环糊精与水碱反应制备的。这种脱水环糊精经 Taka 淀粉酶酶解后，只得到 3″，6″-脱水麦芽四糖。

  DOI：

  10.1246/cl.1988.543
• 作为产物：
  描述：

  Mono-6-O-(p-toluenesulfonyl)-beta-cyclodextrin 生成 Mono-3^A,6^A-anhydrocyclomaltoheptaose
  参考文献：
  名称：

  FUJITA, KAHEE;YAMAMURA, HATSUO;IMOTO, TAIJI;TABUSHI, IWAO, CHEM. LETT.,(1988) N 3, 543-546

  摘要：

  DOI：

文献信息

• A complete series of 6-deoxy-monosubstituted tetraalkylammonium derivatives of α-, β-, and γ-cyclodextrin with 1, 2, and 3 permanent positive charges
  作者：Martin Popr、Simona Hybelbauerová、Jindřich Jindřich

  DOI：10.3762/bjoc.10.142

  日期：——

  An efficient synthetic route toward the preparation of a complete series of monosubstituted tetraalkylammonium cyclodextrin (CD) derivatives is presented. Monotosylation of native CDs (α-, β-, γ-) at position 6 gave the starting material. Reaction of monotosylate (mono-Ts-CD) with 45% aqueous trimethylamine gave CDs substituted with one cationic functional group in a single step. Derivatives equipped with a substituent containing two cationic sites separated by an ethylene or a propylene linker were prepared by reacting mono-Ts-CD with neat N,N,N’-trimethylethane-1,2-diamine or N,N,N’-trimethylpropane-1,3-diamine and subsequent methylation by CH₃I in good yields. Finally, analogues bearing a moiety with three tetraalkylammonium sites were synthesized by reacting mono-Ts-CD with bis(3-aminopropyl)amine and subsequent methylation. The majority of the presented reactions are very straightforward with a simple work-up, which avoids the need of chromatographic separation. Thus, these reactions are suitable for the multigram-scale production of monosubstituted cationic CDs.

  一种高效的合成路线用于制备一系列单取代四烷基铵环糊精（CD）衍生物。在6位点上对天然CDs（α-，β-，γ-）进行单磺酰化得到起始物质。单磺酸酯（单-Ts-CD）与45%水合三甲胺的反应在单步中给出了带有一个阳离子功能基团的CDs取代物。通过将单-Ts-CD与纯净的N,N,N’-三甲基乙烷-1,2-二胺或N,N,N’-三甲基丙烷-1,3-二胺反应，并随后通过CH3I进行甲基化，制备了含有由乙烯或丙烯连接剂分隔的两个阳离子位点的取代物。最后，通过将单-Ts-CD与双(3-氨基丙基)胺反应并随后进行甲基化，合成了带有三个四烷基铵位点的类似物。所提出的大多数反应非常直接，工作简单，避免了色谱分离的需要。因此，这些反应适用于生产单取代阳离子CDs的多克级规模。
• Conformational Effects on Glycoside Reactivity:  Study of the High Reactive Conformer of Glucose
  作者：Ciaran McDonnell、Oscar López、Paul Murphy、José G. Fernández Bolaños、Rita Hazell、Mikael Bols

  DOI：10.1021/ja047476t

  日期：2004.10.1

  The effect of conformation on glycoside reactivity was investigated by studying the hydrolysis of a selection of 3,6-anhydroglucosides as models for glucose in the highly reactive (1)C(4) conformation. Methyl 3,6-anhydro-beta-D-glucopyranoside was found to hydrolyze 200-400 times faster than methyl glucosides in the (4)C(1) conformation, while methyl 3,6-anhydro-beta-D-galactopyranoside, which is in

  构象对糖苷反应性的影响通过研究作为高反应性 (1)C(4) 构象中葡萄糖模型的 3,6-脱水糖苷的选择的水解来研究。发现甲基 3,6-脱水-β-D-吡喃葡萄糖苷比 (4)C(1) 构象中的甲基葡萄糖苷水解快 200-400 倍，而甲基 3,6-脱水-β-D-吡喃半乳糖苷，处于 B(1,4) 构象中，反应性低于甲基 β-D-吡喃半乳糖苷。甲基(3,6-脱水-β-D-吡喃葡萄糖基)-(1 --> 6)-α-D-吡喃葡萄糖苷，甲基(3,6-脱水-α-D-吡喃葡萄糖基)-(1 --> 6 )-α-D-吡喃葡萄糖基-(1 --> 6)-α-D-吡喃葡萄糖苷和甲基(3,6-脱水-β-D-吡喃葡萄糖基)-(1 --> 6)-α-D-吡喃葡萄糖基-(1 --> 6)-α-D-吡喃葡萄糖苷被制备并且发现在脱水残基处选择性地反应。糖苷的 (1)C(4) 构象异构体是高活性物种的发现符合并支持先前的结果，表明轴向
• Regiochemical Correlation between 6-O-Sulfonylated Cyclodextrins and 3-O-Sulfonylated Cyclodextrins via 3,6-Anhydrocyclodextrins
  作者：Kahee Fujita、Tsutomu Tahara、Yoshimitsu Egashira、Hatsuo Yamamura、Taiji Imoto、Toshitaka Koga、Toshihiro Fujioka、Kunihide Mihashi

  DOI：10.1246/cl.1988.705

  日期：1988.4.5

  (3R)-2,3-Anhydrocyclodextrins which were prepared from 3-O-sulfonylcyclodextrins were treated with aqueous alkali to give 3,6-anhydrocyclodextrins, which were prepared by the reaction of 6-O-sulfonylcyclodextrins with aqueous alkali. This regiochemical correlation was applicable to regioisomer determination of 3-O-disulfonylcyclodextrins on the basis of the regiochemistry of 6-O-disulfonates.

  由 3-O-磺酰环糊精制得的 (3R)-2,3-脱氢环糊精经水碱处理后得到 3,6-脱氢环糊精，而 3,6-脱氢环糊精是由 6-O-磺酰环糊精与水碱反应制得的。根据 6-O-二磺酸盐的区域化学性质，这种区域化学相关性适用于 3-O-二磺酰基环糊精的区域异构体测定。
• NMR Spectroscopy on the Complexation of 3,6-Anhydro-β-cyclodextrin with 2,6-Naphthalenedicarboxylate Ion
  作者：Keisuke Yoshikiyo、Yoshihisa Matsui、Tatsuyuki Yamamoto、Yuji Okabe

  DOI：10.1246/bcsj.80.1124

  日期：2007.6.15

  The 2,6-naphthalenedicarboxylate ion (2,6-NDC) was included into the interior cavity of 3A,6A-anhydro-β-cyclodextrin (1) in D2O containing 0.1 mol dm−3 Na2CO3 and caused a shift in the 1H NMR signals due to the C3- and C5-H’s of 1 to different directions, depending on the positions of glucose units (anisotropic ring-current effect). The decrease in entropy accompanied by the complexation was much larger than that for the complexation of native β-cyclodextrin with 2,6-NDC. These results indicate that the molecular rotation of 2,6-NDC is retarded within the deformed cavity of 1.

  2,6-萘二甲酸根离子 (2,6-NDC) 被包含在含有 0.1 mol dm−3 Na2CO3 的 D2O 中的 3A,6A-脱水-β-环糊精 (1) 的内腔中，并引起 1H NMR 的变化由于 1 的 C3- 和 C5-H 导致的信号会向不同方向传播，具体取决于葡萄糖单元的位置（各向异性环电流效应）。络合伴随的熵降低比天然β-环糊精与2,6-NDC络合时的熵降低大得多。这些结果表明 2,6-NDC 的分子旋转在 1 的变形空腔内被延迟。
• 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.