6-O-n-decyl-α,α-D-trehalose | 1392492-60-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-n-decyl-α,α-D-trehalose
• 英文别名: decyl(-6)Glc(a1-1a)Glc；(2R,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-6-(decoxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1392492-60-2
• 化学式: C₂₂H₄₂O₁₁
• 分子量: 482.569
• InChiKey: QZLWFIKLLIDFMK-OALZDZJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  33
• 可旋转键数：
  14
• 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-n-decyl-α,α-D-trehalose 、 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：

  [(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-methanol 在 palladium 10% on activated carbon 、 氢气 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 96.5h， 生成 6-O-n-decyl-α,α-D-trehalose
  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

文献信息

• Synthesis, trehalase hydrolytic resistance and inhibition properties of 4- and 6-substituted trehalose derivatives
  作者：Shari Dhaene、Johan Van der Eycken、Koen Beerens、Jorick Franceus、Tom Desmet、Jurgen Caroen

  DOI：10.1080/14756366.2020.1837125

  日期：2020.1.1

  activity could be of interest. In this study, 34 4- and 6-O-substituted trehalose derivatives were synthesised using an ether- or carbamate-type linkage. Their hydrolysis susceptibility and inhibitory properties were determined against two trehalases, i.e. porcine kidney and Mycobacterium smegmatis. With the exception of three weakly hydrolysable 6-O-alkyl derivatives, the compounds generally showed to be

  摘要 尽管海藻糖由于其药物潜力最近已引起人们的兴趣，但由于其生物利用度低而阻碍了其临床应用。因此，保持生物活性的耐水解的海藻糖类似物可能是令人感兴趣的。在这项研究中，使用醚或氨基甲酸酯型键合成了34种4-和6- O取代的海藻糖衍生物。测定了它们对两种海藻糖酶的水解敏感性和抑制特性，即猪肾和耻垢分枝杆菌。除了三个弱水解的6- O-烷基衍生物，该化合物通常显示出完全抗性。此外，许多衍生物被证明是这些海藻糖酶之一或两者的抑制剂。对于猪肾海藻糖酶的最强抑制剂，可以测定约50 mM的IC 50值，而几种化合物显示出针对耻垢分枝杆菌海藻糖酶的亚mM IC 50值。进行了对接研究以解释观察到的取代模式对猪肾海藻糖酶抑制活性的影响。