6-O-dodecyltrehalose | 1389320-92-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-dodecyltrehalose
• 英文别名: alpha-D-Glucopyranosyl 6-O-dodecyl-alpha-D-glucopyranoside；(2R,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-6-(dodecoxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1389320-92-6
• 化学式: C₂₄H₄₆O₁₁
• 分子量: 510.623
• InChiKey: HIJNTEBBIQHGEK-FXPCSOOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-O-dodecyltrehalose 、 乙酸酐 在 吡啶 作用下， 反应 24.0h， 生成
  参考文献：
  名称：

  Self-assembling properties of 6-O-alkyltrehaloses under aqueous conditions

  摘要：

  In this study, we report the self-assembling properties of 6-O-alkyltrehaloses with different chain lengths, that is, octyl, decyl, dodecyl, tetradecyl, and hexadecyl, under aqueous conditions. The materials were synthesized from trehalose via five reaction steps. The scanning electron microscopy (SEM), transmission electron microscopy (TEM), powder X-ray diffraction (XRD), and dynamic light scattering (DLS) measurements indicated that the self-assembling property of 6-O-dodecyltrehalose was completely different from that of the other derivatives. The former primarily formed spherical micelles in water, which further assembled into face-centered cubic-based aggregates when dried. The latter derivatives, on the other hand, formed vesicle-type particles via the formation of lamellar-like planes, which further merged with each other, most likely by the fusion of the planes, to construct larger aggregates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.05.014
• 作为产物：
  描述：

  海藻糖 在 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 6-O-dodecyltrehalose
  参考文献：
  名称：

  用于膜蛋白研究的十二烷基海藻糖苷去污剂的合成和性质

  摘要：

  糖基洗涤剂，主要来自麦芽糖或葡萄糖，在膜蛋白的提取、增溶、稳定和结晶中占主导地位。受海藻糖广泛用于保护生物大分子和脂质双层结构的启发，我们合成了新的海藻糖苷去污剂，用于膜蛋白研究的潜在应用。我们设计了四种十二烷基海藻糖苷的有效合成方法，每种十二烷基海藻糖苷的 12 碳烷基链连接到海藻糖的不同羟基，从而呈现结构多样但相关的洗涤剂家族。评估洗涤剂的物理特性，包括溶解度、疏水性、临界胶束浓度 (CMC) 和胶束大小，并与最流行的麦芽糖苷类似物 β- d 进行比较。-十二烷基麦芽糖苷 (DDM)，由于不同的分子几何形状和所得胶束中可能的极性基团相互作用而彼此不同。还在甲醇中获得了 2-十二烷基海藻糖苷 (2-DDTre) 的晶体，晶体堆积显示相邻海藻糖基团之间存在多个 H 键相互作用。测试了少数海藻糖苷去污剂对伤害感受素/孤啡肽 FQ 肽受体 (ORL1) 和 MsbA 的溶解和稳定作用，它们分别属于

  DOI：

  10.1021/la3020404

文献信息

• Self-assembling properties of 6-O-alkyltrehaloses under aqueous conditions
  作者：Manami Kanemaru、Kazuya Yamamoto、Jun-ichi Kadokawa

  DOI：10.1016/j.carres.2012.05.014

  日期：2012.8

  In this study, we report the self-assembling properties of 6-O-alkyltrehaloses with different chain lengths, that is, octyl, decyl, dodecyl, tetradecyl, and hexadecyl, under aqueous conditions. The materials were synthesized from trehalose via five reaction steps. The scanning electron microscopy (SEM), transmission electron microscopy (TEM), powder X-ray diffraction (XRD), and dynamic light scattering (DLS) measurements indicated that the self-assembling property of 6-O-dodecyltrehalose was completely different from that of the other derivatives. The former primarily formed spherical micelles in water, which further assembled into face-centered cubic-based aggregates when dried. The latter derivatives, on the other hand, formed vesicle-type particles via the formation of lamellar-like planes, which further merged with each other, most likely by the fusion of the planes, to construct larger aggregates. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and Properties of Dodecyl Trehaloside Detergents for Membrane Protein Studies
  作者：Houchao Tao、Yu Fu、Aaron Thompson、Sung Chang Lee、Nicholas Mahoney、Raymond C. Stevens、Qinghai Zhang

  DOI：10.1021/la3020404

  日期：2012.7.31

  proteins. Inspired by the broad use of trehalose for protecting biological macromolecules and lipid bilayer structures, we synthesized new trehaloside detergents for potential applications in membrane protein research. We devised an efficient synthesis of four dodecyl trehalosides, each with the 12-carbon alkyl chain attached to different hydroxyl groups of trehalose, thus presenting a structurally

  糖基洗涤剂，主要来自麦芽糖或葡萄糖，在膜蛋白的提取、增溶、稳定和结晶中占主导地位。受海藻糖广泛用于保护生物大分子和脂质双层结构的启发，我们合成了新的海藻糖苷去污剂，用于膜蛋白研究的潜在应用。我们设计了四种十二烷基海藻糖苷的有效合成方法，每种十二烷基海藻糖苷的 12 碳烷基链连接到海藻糖的不同羟基，从而呈现结构多样但相关的洗涤剂家族。评估洗涤剂的物理特性，包括溶解度、疏水性、临界胶束浓度 (CMC) 和胶束大小，并与最流行的麦芽糖苷类似物 β- d 进行比较。-十二烷基麦芽糖苷 (DDM)，由于不同的分子几何形状和所得胶束中可能的极性基团相互作用而彼此不同。还在甲醇中获得了 2-十二烷基海藻糖苷 (2-DDTre) 的晶体，晶体堆积显示相邻海藻糖基团之间存在多个 H 键相互作用。测试了少数海藻糖苷去污剂对伤害感受素/孤啡肽 FQ 肽受体 (ORL1) 和 MsbA 的溶解和稳定作用，它们分别属于