6-monodeoxy-6-monoamino-(2-O-methyl)-hexakis(2,6-di-O-methyl)-β-cyclodextrin | 133125-61-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-monodeoxy-6-monoamino-(2-O-methyl)-hexakis(2,6-di-O-methyl)-β-cyclodextrin
• 英文别名: mono(6-amino-6-deoxy-2-O-methyl)-hexakis-(2,6-di-O-methyl)-β-cyclodextrin；mono(6-amino-6-desoxy-2-O-methyl)hexakis(2,6-di-O-methyl)-β-cyclodextrine；mono(6-amino-6-deoxy-2-O-methyl)hexakis(2,6-di-O-methyl)-β-cyclodextrin；(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36S,37R,38S,39R,40S,41R,42S,43R,44S,45R,46S,47R,48S,49R)-5-(aminomethyl)-37,39,41,43,45,47,49-heptamethoxy-10,15,20,25,30,35-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-36,38,40,42,44,46,48-heptol
• CAS: 133125-61-8
• 化学式: C₅₅H₉₇NO₃₄
• 分子量: 1316.36
• InChiKey: YFLBHGBVLZITGY-DXJNWUIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.76
• 重原子数：
  90.0
• 可旋转键数：
  20.0
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  416.84
• 氢给体数：
  8.0
• 氢受体数：
  35.0

反应信息

• 作为反应物：
  描述：

  Boc-D-苯丙氨酸 、 6-monodeoxy-6-monoamino-(2-O-methyl)-hexakis(2,6-di-O-methyl)-β-cyclodextrin 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以43%的产率得到mono(6-N-tert-butyloxycarbonyl-R-phenylalanylamino-6-desoxy-2-O-methyl)-hexakis(2,6-di-O-methyl)-β-cyclodextrine
  参考文献：
  名称：

  Parrot-Lopez, H.; Galons, H.; Dupas, S., Bulletin de la Societe Chimique de France, 1990, # 4, p. 568 - 571

  摘要：

  DOI：
• 作为产物：
  描述：

  mono(6-azido-6-deoxy-2-O-methyl)hexakis(2,6-di-O-methyl)-β-cyclodextrin 在 palladium on activated charcoal 、 氢气 作用下， 以 水 为溶剂， 反应 18.0h， 以82%的产率得到6-monodeoxy-6-monoamino-(2-O-methyl)-hexakis(2,6-di-O-methyl)-β-cyclodextrin
  参考文献：
  名称：

  Synthesis and inclusion properties study of some mono 6-amino β-cyclodextrin dimers bridged by N,N-succinyldiamide linkers

  摘要：

  合成了通过二氨基丁二酸桥连接的甲基化和部分甲基化环糊精同二聚体和异二聚体，并使用核磁共振和等温微量热测量法（ITC）评估了它们的包合特性。配体（如双金刚烷基衍生物）与未受保护的环糊精二聚体空腔的选择性结合显示，双端酸盐包合物的形成是等摩尔的（2:2，两个配体客体对两个空腔主体）。

  DOI：

  10.1007/s10847-010-9816-2

文献信息

• α-Phenyl-N-tert-butylnitrone-Type Derivatives Bound to β-Cyclodextrins: Syntheses, Thermokinetics of Self-Inclusion and Application to Superoxide Spin-Trapping
  作者：David Bardelang、Laurence Charles、Jean-Pierre Finet、Laszlo Jicsinszky、Hakim Karoui、Sylvain R. A. Marque、Valérie Monnier、Antal Rockenbauer、Roseline Rosas、Paul Tordo

  DOI：10.1002/chem.200700369

  日期：2007.11.16

  alpha-Phenyl-N-tert-butylnitrone (PBN) derivatives bound to beta-cyclodextrin derivatives have been synthesized. Inclusion of the PBN group into the beta-cyclodextrin moiety is host- and temperature-dependent. In the case of the nitrone linked to permethylated cyclodextrin (Me3CD-PBN), the thermokinetic parameters are in favour of a slow chemical exchange between a tight and a loose complex. In contrast

  已经合成了与β-环糊精衍生物结合的α-苯基-N-叔丁基硝基（PBN）衍生物。PBN基团包含在β-环糊精部分中是宿主和温度依赖的。在将硝酮连接至全甲基化环糊精（Me3CD-PBN）的情况下，热动力学参数有利于紧密配合物和疏松配合物之间的缓慢化学交换。相反，2,6-二-O-Me-β-环糊精接枝的PBN（Me2CD-PBN）要么以快速交换的形式存在，要么以强烈的自缔合形式存在。共价环糊精-PBN化合物已用于捕获以碳和氧为中心的自由基。β-CD-spin-traps的自缔合形式与有效的spin-trapping兼容，相对于非共价CD-硝酮系统或仅使用硝酮，可提供具有增强的EPR信号强度的自旋加合物。这种与环糊精结合的硝酮是共价超分子自旋捕集的第一种类型，应该为体内生物自由基的研究开辟新的可能性。
• Bahaddi, Youssef; Galons, Herve; Rysanek, Nicole, Bulletin de la Societe Chimique de France, 1995, vol. 132, p. 330 - 332
  作者：Bahaddi, Youssef、Galons, Herve、Rysanek, Nicole

  DOI：——

  日期：——
• A sensitive and specific enzyme immunoassay for the detection of methyl ether derivatives of cyclomaltoheptaose
  作者：Florence Djedaı̈ni-Pilard、Marie-Claire Nevers、Sandrine Weisse、Jacques Grassi、Bruno Perly、Christophe Créminon

  DOI：10.1016/s0008-6215(03)00311-2

  日期：2003.9

  We have raised antibodies against two methylated derivatives of beta-CD, heptakis(2,6-di-O-methyl)cyclomaltoheptaose (Dimeb) and heptakis(2,3,6-tri-O-methyl)cyclomaltoheptaose (Trimeb). These antibodies were used to develop two specific and sensitive enzyme immunoassays, presenting a detection limit close to 500 and 30 pg/mL for Trimeb and Dimeb, respectively. Cross reactivities of different linear and cyclic maltooligosaccharides were investigated, demonstrating a high specificity against the structural features of the secondary hydroxyls rim. Several commercial Dimeb samples, containing different mixtures of partially methylated beta-cyclodextrin derivatives including RAMEB, which contains only a few amount of pure Dimeb, could be easily evaluated by the Dimeb immunoassay. Both of these assays have been shown to allow accurate measurement in plasma and urine, thus appearing as useful tools for further applications in biological material. (C) 2003 Elsevier Ltd. All rights reserved.
• PARROT-LOPEZ, H.;GALONS, H.;DUPAS, S.;MIOCQUE, M.;TSOUCARIS, G., BULL. SOC. CHIM. FR.,(1990) N, C. 568-571
  作者：PARROT-LOPEZ, H.、GALONS, H.、DUPAS, S.、MIOCQUE, M.、TSOUCARIS, G.

  DOI：——

  日期：——
• Dynamic Multivalent Lactosides Displayed on Cyclodextrin Beads Dangling from Polymer Strings
  作者：Alshakim Nelson、J. Fraser Stoddart

  DOI：10.1021/ol0353464

  日期：2003.10.1

  [GRAPHICS]Lactose-appended cyclodextrin derivatives have been synthesized and threaded onto hydrophobic polymers in aqueous solution to form dynamic multivalent lactosides for binding to lectins. The threading process, which proceeds quickly, can be observed by one- and two-dimensional NMR spectroscopies.