D-(+)-海藻糖6-单油酸酯 | 338733-38-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 中文名称: D-(+)-海藻糖6-单油酸酯
• 英文名称: 6-O-oleoyl-α,α-trehalose
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl (Z)-octadec-9-enoate
• CAS: 338733-38-3
• 化学式: C₃₀H₅₄O₁₂
• 分子量: 606.752
• InChiKey: MLVMMWOWJSIKLS-WYVBACLFSA-N

物化性质

• 熔点：
  165-167 °C
• 沸点：
  760.6±60.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  42
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

安全信息

• WGK Germany：
  3
• 储存条件：
  |-20°C|

反应信息

• 作为反应物：
  描述：

  13-甲基十四烷酸 、 D-(+)-海藻糖6-单油酸酯 在 六甲基磷酰三胺 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 反应 72.0h， 以69%的产率得到6-O-(13-methyltetradecanoyl)-6'-O-oleoyl-α,α-trehalose
  参考文献：
  名称：

  Synthesis of a maradolipid without using protecting groups

  摘要：

  A convenient route has been developed to synthesize 6-O-mono- and 6,6'-di-O-acyl symmetrical and unsymmetrical (un)-symmetrically trehalose derivatives from trehalose using a combination of enzymic and nonenzymic reactions. Thus, a typical maradolipid was accessed in two-steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.076
• 作为产物：
  描述：

  海藻糖 、 (9Z)-9-十八碳烯酸乙烯基酯 在 alcalase from Bacillus licheniformis 作用下， 以 丙酮 为溶剂， 反应 432.0h， 以72%的产率得到D-(+)-海藻糖6-单油酸酯
  参考文献：
  名称：

  Synthesis of a maradolipid without using protecting groups

  摘要：

  A convenient route has been developed to synthesize 6-O-mono- and 6,6'-di-O-acyl symmetrical and unsymmetrical (un)-symmetrically trehalose derivatives from trehalose using a combination of enzymic and nonenzymic reactions. Thus, a typical maradolipid was accessed in two-steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.076

文献信息

• Trehalose Monooleate: A Potential Antiaggregation Agent for Stabilization of Proteins
  作者：Smita S. Kale、Krishnacharya G. Akamanchi

  DOI：10.1021/acs.molpharmaceut.6b00686

  日期：2016.12.5

  aggregation decreases their therapeutic activity and shelf life and induces immunogenicity. Stabilization against aggregation is commonly attained by addition of different excipients like sugars, surfactants, buffers, salts, amino acids, polymers, etc. Generally these excipients are required in combination for stabilization. Sugars are required at a higher concentration, and commonly used surfactants like polysorbates

  蛋白质聚集是治疗性蛋白质的主要问题，因为聚集会降低其治疗活性和保质期并诱导免疫原性。通常通过添加不同的赋形剂（如糖，表面活性剂，缓冲液，盐，氨基酸，聚合物等）来实现对聚集的稳定化。通常，需要将这些赋形剂结合在一起以稳定化。需要较高浓度的糖，并且由于氧化降解，常用的表面活性剂如聚山梨酯具有缺点。为了使多功能赋形剂在较低的浓度下有效，我们设计了抗凝集剂（AAAs），它包含两种或更多种常规赋形剂的功能，并且会减少为稳定而添加的赋形剂的数量。我们第一个设计的AAA，海藻糖单油酸酯（TMO）是一种糖脂肪酸衍生物。已被评估在计算机上通过停靠在模型蛋白牛血清白蛋白（BSA）的易于凝集的区域上，并通过实验验证了其有效性，可作为抗搅动和热应激的稳定剂。TMO的CMC较低，为6 mg / L，具有非溶血性，在人肝癌细胞系（Hep-G2）中以阿霉素为阳性对照，通过磺基罗丹明B（SRB）比色测定发现无毒。在存在和
• Direct Synthesis of Maradolipids and Other Trehalose 6-Monoesters and 6,6′-Diesters
  作者：Nawal K. Paul、Jean-d’Amour K. Twibanire、T. Bruce Grindley

  DOI：10.1021/jo302231v

  日期：2013.1.18

  It was shown that reaction of trehalose with 1 equiv of a fatty acid in pyridine promoted by 1 equiv of the uronium-based coupling agent 2-(1H-benzotriazole-1-y1)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) at room temperature gives a good yield of the primary ester accompanied by small amounts of the diprimary ester using hexanoic, palmitic, and oleic acids as examples. Reactions using 2 equiv of the fatty acids gave the symmetrical diesters. The monoesters were reacted with different fatty acids to give nonsymmetric 6,6'-diesters in very good yields. Compounds synthesized include the most abundant component of the very complex maradolipid mixture, 6-O-(13-methyltetradecanoyl)-6'-O-oleoyltrehalose, and a component potentially present in this mixture, 6-O-(12-methyltetradecanoyl)-6'-O-oleoyltrehalose, a derivative of an ante fatty acid. The CS-C6 rotameric populations of 6-O-monoesters, symmetrical 6,6'-diesters, and 2,6,6'-triesters of fatty acids were calculated from the values of the H5-H6R and H5-H6S coupling constants and found to be similar to those found for glucose. The rotameric populations of the monosubstituted glucose residues in the 2,6,6'-triesters was altered considerably to favor the gt rotamer, presumably because of attraction between the 2- and 6'-fatty acid chains.