(R)-3-(dodecanoyloxy)tetradecanoic acid | 338952-12-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-3-(dodecanoyloxy)tetradecanoic acid
• 英文别名: (3R)-3-dodecoxytetradecanoic acid
• CAS: 338952-12-8
• 化学式: C₂₆H₅₂O₃
• 分子量: 412.697
• InChiKey: QILHWRXUKHLXAZ-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  29
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-(dodecanoyloxy)tetradecanoic acid 在 四氮唑 、 4-二甲氨基吡啶 、 二甲胺基甲硼烷 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 [(2R,3S,4R,5R,6R)-3-bis(phenylmethoxy)phosphoryloxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-dodecoxytetradecanoate
  参考文献：
  名称：

  Lipid A structures containing novel lipid moieties: synthesis and adjuvant properties

  摘要：

  Structurally well-defined immune stimulatory molecules are important components of new generation molecular vaccines. In this paper, the design and synthesis of two lipid A analogues containing an unnatural tri-lipid acyl group are described. In a totally synthetic liposomal vaccine system, these re-designed lipid A analogues demonstrate potent immune stimulatory properties including antigen specific T-cell activation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00362-1
• 作为产物：
  描述：

  (3R)-3-hydroxytetradecanoic acid phenacyl ester 在 potassium carbonate 、 溶剂黄146 、 锌 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 (R)-3-(dodecanoyloxy)tetradecanoic acid
  参考文献：
  名称：

  Lipid A structures containing novel lipid moieties: synthesis and adjuvant properties

  摘要：

  Structurally well-defined immune stimulatory molecules are important components of new generation molecular vaccines. In this paper, the design and synthesis of two lipid A analogues containing an unnatural tri-lipid acyl group are described. In a totally synthetic liposomal vaccine system, these re-designed lipid A analogues demonstrate potent immune stimulatory properties including antigen specific T-cell activation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00362-1

文献信息

• Efficient synthesis of novel monosaccharide analogs of lipids A.
  作者：Shinichi Nakamoto、Toshio Takahashi、Kiyoshi Ikeda、Kazuo Achiwa

  DOI：10.1248/cpb.33.4098

  日期：——

  The efficient synthesis of the monosaccharide analogs of lipids A bearing two 3-acyloxytetradecanoyl and phosphoryl groups at the C-2, 3 and C-4 positions of the glucosamine skeleton is described. Also a preliminary analysis of their biological activities is presented.

  描述了具有两个3-酰氧基十四酸和磷酸基团在葡萄糖胺骨架的C-2、C-3和C-4位置的脂质A单糖类似物的高效合成。此外，还呈现了对其生物活性的初步分析。
• Synthesis and bioactivity of a fluorescence-labeled lipid A analogue
  作者：Masato Oikawa、Hiroki Furuta、Yasuo Suda、Shoichi Kusumoto

  DOI：10.1016/s0040-4039(99)00937-5

  日期：1999.7

  A fluorescence-labeled phosphonooxyethyl (PE) analogue of lipid A has been successfully synthesized in 15 steps from D-glucosamine derivative 2 in total 16% yield. The analogue exhibits Limulus activity and cytokine-inducing activity similar to the natural lipopolysaccharide and the unlabeled PE analogue of lipid A.

  脂质A的荧光标记的膦酰氧乙基（PE）类似物已成功地以15个步骤从D-葡萄糖胺衍生物2合成，总收率为16％。该类似物表现出Li活性和诱导细胞因子的活性，类似于天然脂多糖和脂质A的未标记PE类似物。
• Synthesis and evaluation of monophosphoryl lipid A derivatives as fully synthetic self-adjuvanting glycoconjugate cancer vaccine carriers
  作者：Zhifang Zhou、Mohabul Mondal、Guochao Liao、Zhongwu Guo

  DOI：10.1039/c4ob00390j

  日期：——

  immunological properties of tumor-associated carbohydrate antigens (TACAs). In this context, four monophosphoryl derivatives of Neisseria meningitidis lipid A were synthesized via a highly convergent and effective strategy and evaluated as vaccine carriers and adjuvants. The conjugates of these monophosphoryl lipid A (MPLA) derivatives with a modified form of the sTn antigen were found to elicit high

  完全合成的基于碳水化合物的癌症疫苗是一个有吸引力的概念，但该领域的一个重要课题是开发合适的疫苗载体，以提高肿瘤相关碳水化合物抗原 (TACA) 的免疫原性和其他免疫学特性。在此背景下，通过合成脑膜炎奈瑟菌脂质 A 的四种单磷酰衍生物高度收敛和有效的策略，并被评估为疫苗载体和佐剂。发现这些单磷酰脂质 A (MPLA) 衍生物与 sTn 抗原的修饰形式的缀合物在没有外部佐剂的情况下引发高滴度的抗原特异性 IgG 抗体，表明 T 细胞依赖性免疫反应。结论是 MPLA 可用作有效的疫苗载体和内置佐剂，以创建完全合成的基于碳水化合物的自佐剂癌症疫苗。MPLA 的脂质组成和结构显示对其免疫活性有显着影响，在检查的 MPLA 中，天然脑膜炎奈瑟菌MPLA 表现出最有前途的特性。此外，常规疫苗佐剂 Titermax Gold 可能通过与 MPLA 相互作用来抑制而不是促进 MPLA 偶联物的免疫活性。
• Synthesis of GLA-60 type pyran carboxylic acids with an alkyl chain instead of an ester chain as LPS-antagonists
  作者：Yukiko Watanabe、Kumiko Miura、Masao Shiozaki、Saori Kanai、Shin-ichi Kurakata、Masahiro Nishijima

  DOI：10.1016/s0008-6215(01)00055-6

  日期：2001.6

  Synthesis of GLA-60 type pyran carboxylic acid analogues with an alkyl chain instead of an ester chain and their LPS-antagonist activity toward human U937 cells are described. (C) 2001 Elsevier Science Ltd. All rights reserved.
• SYNTHETIC LIPID-A ANALOGS AND USES THEREOF
  申请人：Oncothyreon Inc.

  公开号：EP1232168B1

  公开（公告）日：2011-08-03