β-cyclodextrin monoaldehyde | 159496-21-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-cyclodextrin monoaldehyde
• 英文别名: 6A-Deoxy-6A-oxo-|A-cyclodextrin；(1S,3R,5R,6S,8S,10S,11S,13R,15R,16S,18R,20R,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-5,15,20,25,30,35-hexakis(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-10-carbaldehyde
• CAS: 159496-21-6
• 化学式: C₄₂H₆₈O₃₅
• 分子量: 1132.98
• InChiKey: LAIARMSZQYZZKT-FOUAGVGXSA-N

物化性质

• 熔点：
  297-299 °C (decomp)
• 沸点：
  1536.3±65.0 °C(Predicted)
• 密度：
  1.649±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -14.8
• 重原子数：
  77
• 可旋转键数：
  7
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  551
• 氢给体数：
  20
• 氢受体数：
  35

反应信息

• 作为反应物：
  描述：

  β-cyclodextrin monoaldehyde 在 phosphate buffer 、 溴 作用下， 反应 120.0h， 以20%的产率得到mono-6-deoxy-6-carboxy-β-cyclodextrin
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of a new targeted drug carrier system: β-Cyclodextrin coupled to oxytocin

  摘要：

  beta-Cyclodextrin (beta-CD) was monofunctionalized into its carboxylic derivative and then conjugated to the N-side of oxytocin (OT), a nonapeptide involved in human behavior and myometrium contraction. On isolated rat myometrium, this conjugate (beta-CD-OT) partly preserves the contracting activity of OT (EC50 = 0.40 mu M vs 1.7 nM). Moreover, the contraction induced frequency is also lowered by beta-CD-OT. This novel hydrophilic targeted carrier could form a host-guest complex with prostaglandins and their derivatives used as labor inducers or with anticancer drugs used in cervix and endometrial cancer. This strategy can improve the solubility, the stability, and/or the biological activity of these drugs as well as reducing their side-effects. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.017
• 作为产物：
  描述：

  6^A-aldehydo-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-benzyl-β-cyclodextrin 在 氢气 、 palladium(II) hydroxide 作用下， 生成 β-cyclodextrin monoaldehyde
  参考文献：
  名称：

  Simple cyclodextrin aldehydes as excellent artificial oxidases

  摘要：

  众所周知，以酮为官能团的环糊精氧化酶是良好的人工酶模拟物（Fenger et al.Org Biomol Chem 7:933-943; Marinescu and Bols Angew Chem Int Ed 45:4590-4593; Bjerre et al.Eur J Org Chem 704-710; Marinescu et al.J Am Chem Soc 127:17578-17579）。我们在此报告了一系列以醛为官能团的改性环糊精。在大多数情况下，以醛为基础的人工酶比酮类具有更好的催化作用，因为它们能与过氧化氢产生强大的共价结合。在所研究的改性环糊精中，有 6 个位置上的单醛和二醛，有或没有甲基化羟基。此外，还通过在 2 位上连接乙氧基-2-al 或丙氧基-3-al，在靠近仲侧的位置引入了醛官能团。修饰后的环糊精对不同氨基苯酚和 4-甲氧基苯甲醇（以过氧化氢作为定量氧化剂）的氧化显示出卓越的酶活性。氧化 4-甲氧基苯甲醇的速率可提高到 4 600，而氧化胺的速率可提高到 3 400。人工氧化酶在酶促条件下（水、pH 值 7、25 °C），按照 Michaelis-Menten 动力学催化氧化。为了证实酶的活性，还用萘-2-磺酸钠进行了抑制研究。这些研究显示了对酶的竞争性抑制，验证了环糊精的酶类似特性。

  DOI：

  10.1007/s10847-010-9771-y

文献信息

• pH- and Thermosensitive Supramolecular Assembling System:  Rapidly Responsive Properties of β-Cyclodextrin-Conjugated Poly(ε-lysine)
  作者：Hak Soo Choi、Kang Moo Huh、Tooru Ooya、Nobuhiko Yui

  DOI：10.1021/ja034149x

  日期：2003.5.1

  β-Cyclodextrin-conjugated poly(e-lysine) (β-CDPL) was synthesized as a novel polymeric host for constructing a smart supramolecular assembling system. Systematic studies on the inclusion complexation between the polymeric host with an α- or β-CD cavity and a model guest molecule provided evidence that dual cooperative interactions, specific host−guest interaction and intermolecular ionic interaction

  β-环糊精共轭聚（e-赖氨酸）（β-CDPL）被合成为一种新型聚合物主体，用于构建智能超分子组装系统。对具有 α- 或 β-CD 腔的聚合物主体与模型客体分子之间的包合络合的系统研究提供了证据，表明双重协同相互作用、特定的主客体相互作用和分子间离子相互作用在导致快速聚集现象。此外，响应于 pH 值或温度的微小变化，观察到由超分子组装诱导的快速相变可逆。
• Synthesis of 6-Mono-6-deoxy-β<i>-</i>cyclodextrins Substituted with Isomeric Aminobenzoic Acids. Structural Characterization, Conformational Preferences, and Self-inclusion as Studied by NMR Spectroscopy in Aqueous Solution and by X-ray Crystallography in the Solid State
  作者：Kyriaki Eliadou、Petros Giastas、Konstantina Yannakopoulou、Irene M. Mavridis

  DOI：10.1021/jo034503+

  日期：2003.10.1

  characterization of mono-6-modified-beta-cyclodextrins bearing N-attached o-, m-, and p-aminobenzoic acids (2, 3, and 4, respectively) are presented. The structures in aqueous solution were investigated using one- and two-dimensional NMR spectroscopy. Detailed assignment of the spectra together with intramolecular NOE correlations revealed the way each of the isomeric appendages is positioned relative to the

  本文介绍了合成，纯化和表征带有N-连接的邻氨基，邻氨基和对氨基苯甲酸（分别为2、3和4）的单-6修饰的β-环糊精。使用一维和二维NMR光谱研究水溶液中的结构。光谱的详细分配以及分子内NOE相关性揭示了每个异构体附属物相对于大环腔的定位方式。没有观察到自我包容。o-异构体2向内翻过一次侧的顶部，并与取代的吡喃葡萄糖单元A和邻近单元的特定质子相互作用。间异构体3显示两个构象，其中取代基以倾斜的方式位于伯侧上方，并且与前一个或下一个单元相互作用。我们建议，在2和3中的羧基分别通过与相邻的吡喃葡萄糖单元的一个或两个伯羟基进行H键结合而定位。在对位异构体4的芳环的类似位置中，亲水性羧基末端完全暴露于水性环境。X射线4的结构表明溶液构象已经演化，使得在结晶状态下，芳族部分通过其羧基部分插入另一个CD内，在该CD上建立了具有向内转化的伯OH基团的分子间H键。除了这种稳定作用外，4还在晶体中形成平行和反平
• Facile preparation of the β-cyclodextrinyl aldehyde
  作者：Kristy A. Martin、Anthony W. Czarnik

  DOI：10.1016/0040-4039(94)85003-8

  日期：1994.9

  This paper describes the synthesis and characterization of the 1° - side β-Cyclodextrinyl Monoaldehyde in two steps from β-cyclodextrin.

  本文从β-环糊精分两步描述了1°-侧β-环糊精基单醛的合成和表征。
• Cooperative molecular recognition of dyes by dyad and triad cyclodextrin–crown ether conjugates
  作者：Yu Liu、Ying-Wei Yang、Lei Li、Yong Chen

  DOI：10.1039/b402841d

  日期：——

  Three beta-cyclodextrin (beta-CyD) derivatives with crown ether units, that is N-(4'-benzo-15-crown-5)-6-imino-6-deoxy-beta-CyD (2), 6,6'-[N-(4,4'-dibenzo-18-crown-6)-imino]-bridged bis(beta-CyD)(3), and 2,2'-[O-(4',5'-benzo-15-crown-5)-ethyl]-bridged bis (beta-CyD)(5), were synthesized as cooperative recognition receptor models. Their molecular binding behavior with four representative fluorescent dyes

  具有冠醚单元的三种β-环糊精（β-CyD）衍生物，即N-（4'-苯并15-冠5）-6-亚氨基-6-脱氧-β-CyD（2），6,6 '-[N-（4,4'-dibenzo-18-crown-6）-亚氨基]-桥双（beta-CyD）（3）和2,2'-[O-（4'，5'-苯并15冠5）-乙基]-桥双（β-CyD）（5），被合成为协同识别受体模型。它们与四种代表性荧光染料的分子结合行为，即8-苯胺基-1-磺酸铵（ANS），6-甲苯基-2-萘磺酸钠（TNS），A啶红（AR）和若丹明B（RhB）用圆二色性，NMR和荧光光谱法在25℃的缓冲溶液（pH ＝ 7.20）中研究了H 2 O 3。2D-ROESY实验表明，二元组宿主2和三元组宿主3采用CyD-来宾-冠醚结合模式，而三合会宿主5在与客体分子发生包涵体复合时采用CyD-guest-CyD结合模式。因此，宿主2和宿主3对带电荷的客人表现出较高的分子识别
• β-Cyclodextrin/protein conjugates as a innovative drug systems: synthesis and MS investigation
  作者：Tomasz Girek、Tomasz Goszczyński、Beata Girek、Wojciech Ciesielski、Janusz Boratyński、Piotr Rychter

  DOI：10.1007/s10847-012-0132-x

  日期：2013.4

  The design of proteins whose structure and function can be manipulated by binding with specific ligands such as cyclodextrins, has been of great interest in the field of protein engineering and also could be used as drug delivery systems in targeted cancer therapy (Loftsson and Duchêne, Int. J. Pharm. 329:1–11, 1; Loftsson et al., Expert. Opin. Drug Deliv. 2:335–351, 2). CD/proteins conjugates are synthesized using original high temperature method in which mono-6-O-formyl-β-CD reacts with two proteins: basic pancreatic trypsin inhibitor and lysozyme. The proposed synthesis method has a high reproducibility which makes it useful for pharmaceutical purposes. That method allows to obtain the conjugate without losing protein’s biological and enzymatic activity which will used in the reaction, and without violating the chemical structure of cyclodextrin molecules.

  通过与环糊精等特定配体结合来操纵蛋白质结构和功能的设计，在蛋白质工程领域引起了极大的兴趣，也可用作癌症靶向治疗的药物输送系统（Loftsson 和 Duchêne，Int.J. Pharm.329:1-11，1；Loftsson 等人，Expert.Opin.Drug Deliv.2:335-351, 2).CD/ 蛋白质共轭物采用独创的高温方法合成，其中单-6-O-甲酰基-β-CD 与两种蛋白质（碱性胰蛋白酶抑制剂和溶菌酶）发生反应。所提出的合成方法具有很高的可重复性，因此可用于制药目的。这种方法可以在不损失反应中使用的蛋白质的生物活性和酶活性的情况下获得共轭物，而且不会破坏环糊精分子的化学结构。