(2R)-2-hydroxyoctadecanoic acid | 26633-48-7

• 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: (2R)-2-hydroxyoctadecanoic acid
• 英文别名: (+)-2-hydroxioctadecenoic acid；(R)-2-hydroxyoctadecanoic acid；2R-hydroxyoctadecanoic acid；(R)-2-hydroxystearic acid
• CAS: 26633-48-7
• 化学式: C₁₈H₃₆O₃
• 分子量: 300.482
• InChiKey: KIHBGTRZFAVZRV-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-2-hydroxyoctadecanoic acid 在 吡啶 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 2,5-dioxopyrrolidin-1-yl (2R)-2-acetoxyoctadecanoate
  参考文献：
  名称：

  具有神经生成活性的神经节苷脂DSG-A的首次全合成†

  摘要：

  神经节苷脂DSG-A的第一个全合成（1）是通过化学选择性糖基化和[1 + 1 + 2]合成策略实现的。我们还开发了一种可以大规模（50 g）处理的植物鞘氨醇合成方法。

  DOI：

  10.1039/c4ob01882f
• 作为产物：
  描述：

  (R)-4-benzyl-3-((R)-2-hydroxyoctadecanoyl)oxazolidin-2-one 在 双氧水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以15%的产率得到(2R)-2-hydroxyoctadecanoic acid
  参考文献：
  名称：

  Stereoselective synthesis of unnatural (2S,3S)-6-hydroxy-4-sphingenine-containing sphingolipids

  摘要：

  使用水锆化反应和不寻常的三步一锅脱保护序列，简洁地合成含有鞘氨醇脂类的unnatural (2S,3S)-6-羟基-4-鞘氨醇。

  DOI：

  10.1039/c9ob00990f

文献信息

• NOVEL SHINGOGLYCOLIPID AND USE THEREOF
  申请人：KIRIN BEER KABUSHIKI KAISHA

  公开号：EP0666268A1

  公开（公告）日：1995-08-09

  A shingoglycolipid represented by general formula (I), which is efficiacious even when administered in a small amount, is reduced in side effects, and has antitumor and immunopotentiating activities, wherein X and Y represent respectively integers of 10 to 24 and 9 to 13; R₁ represents hexosyl, pentosyl, deoxyhexosyl, aminohexosyl, N-acetyl aminohexosyl, a halogenated derivative of any of them, or a sialic acid residue; R₂ represents H or OR₂', wherein R₂' represents H, galactosyl or glucosyl; R₃ represents H or OR₃', wherein R₃' represents H, galactosyl or glucosyl; R₄ represents galactosyl or H; R₅ represents methyl or isopropyl; and R₆ and R₇ represent each independently H or alternatively they are combined together to represent a double bond between the carbon atoms to which they are respectively bonded; provided that the case where R₁ represents α-galactosyl and R₄ represents H is excepted.

  一种由通式(I)代表的 shingoglycolipid，即使少量给药也有效，副作用小，并具有抗肿瘤和免疫增强活性，其中 X 和 Y 分别代表 10 至 24 和 9 至 13 的整数；R₁ 代表己糖基、戊糖基、脱氧己糖基、氨基己糖基、N-乙酰氨基己糖基、其中任何一种的卤代衍生物或硅铝酸残基； R₂ 代表 H 或 OR₂'，其中 R₂' 代表 H、半乳糖基或葡萄糖基；R₃ 代表 H 或 OR₃'，其中 R₃' 代表 H、半乳糖基或葡萄糖基； R₄ 代表半乳糖基或 H； R₅ 代表甲基或异丙基；以及 R₆ 和 R₇ 各自独立地代表 H，或者它们组合在一起代表它们分别键合的碳原子之间的双键；但 R₁ 代表 α-半乳糖基而 R₄ 代表 H 的情况除外。
• Probe compound for detecting and isolating enzymes and means and methods using the same
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP2230312A1

  公开（公告）日：2010-09-22

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.

  本发明涉及一种探针化合物，它可以包括酶反应的任何底物或代谢物，此外还包括指示成分，例如荧光染料或类似物。此外，本发明还涉及以阵列形式检测酶的方法，该阵列由任意数量的本发明探针化合物组成，每种探针化合物由代表所有生命形式中中心途径的相互关联的代谢物中的不同代谢物组成。此外，本发明还涉及一种检测酶的方法，该方法涉及将细胞提取物或类似物应用于本发明的阵列，从而导致与底物发生可重复的酶反应。这些特定的酶反应会触发指示剂（如荧光信号），并将酶与各自的同源底物结合。此外，本发明还涉及以涂覆有本发明探针化合物的纳米颗粒形式分离酶的方法。通过探针化合物将同源底物或代谢物固定在纳米颗粒表面，可以捕获和分离相应的酶，例如用于后续测序。
• Cerebrosides fromfomitopsis pinicola (Sw. Ex Fr.) Karst.
  作者：S. Striegler、E. Haslinger

  DOI：10.1007/bf00817267

  日期：——

  A cerebroside fraction was obtained from the fruit bodies of fomitopsis pinicola using column chromatography and then separated into six compounds by reversed-phase HPLC. The sugar component of all cerebrosides was D-glucose. The major fatty acids were 2-hydroxyfatty acids (C-14-C-18), the long chain base was identified as 9-methyl-C-18-4,8-sphingadienine which is widely distributed in fungi and reported to be essential for the fruit-inducing activity of fungi. Based on degradation studies, fast atom bombardment mass spectrometry, and different H-1 and C-13 NMR investigations, the structure of the main cerebroside (1) was determined to be (4E,8E,2S,3R,2'R)-N-2'-hydroxypalmityl-1-O-beta-D-glucopyranosyl-9-methyl-4,8-sphingadienine.
• Abe, Tatsuichirou; Mori, Kenji, Bioscience, Biotechnology and Biochemistry, 1994, vol. 58, # 9, p. 1671 - 1674
  作者：Abe, Tatsuichirou、Mori, Kenji

  DOI：——

  日期：——
• Keratin fiber strengthening agent and method for strengthening keratin fiber
  申请人：Takasago International Corporation

  公开号：EP0920852B1

  公开（公告）日：2005-06-01