methyl (R)-3-hydroxy-15-methyl-hexadecanoate | 103196-77-6

• 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: methyl (R)-3-hydroxy-15-methyl-hexadecanoate
• 英文别名: methyl (R)-3-hydroxy-15-methylhexadecanoate；methyl (3R)-3-hydroxy-15-methylhexadecanoate
• CAS: 103196-77-6
• 化学式: C₁₈H₃₆O₃
• 分子量: 300.482
• InChiKey: KQDAASZNDDREDE-QGZVFWFLSA-N

物化性质

• 熔点：
  32-34 °C
• 沸点：
  399.0±15.0 °C(Predicted)
• 密度：
  0.917±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  methyl (R)-3-hydroxy-15-methyl-hexadecanoate 在 sodium hydroxide 、 endo-N-Hydroxy-5-norbornene-2,3-dicarboximide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 47.5h， 生成 (2R,3R,3'R)-3-hydroxy-2-(3'-hydroxy-15'-methylhexadecanoylamino)-15-methyl-hexadecan-1-sulfonic acid
  参考文献：
  名称：

  通过动态外消旋β-酮-α-氨基酯盐酸盐的动力学拆分，可完全合成磺胺嘧啶A

  摘要：

  描述了磺胺嘧啶A（一种von Willebrand因子受体拮抗剂）的总合成。我们的合成方法独特地依靠催化不对称反应来创建三个立体异构中心，而无需使用手性结构单元。短途生产硫磺巴星A的关键步骤涉及钌介导的β-酮酯和外消旋β-酮-α-氨基酯盐酸盐的不对称氢化反应，分别得到相应的对映体纯的β-羟基酯和对映体。通过动态动力学拆分得到对映体富集的抗β-羟基α-氨基酯盐酸盐。

  DOI：

  10.1016/j.tetasy.2004.05.004
• 作为产物：
  描述：

  13-甲基十四烷酸 在 ruthenium trichloride 氢气 、 (R)-(+)-(6,6′-二甲氧联苯-2,2′-二基)双(二苯基膦) 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0~80.0 ℃ 、600.0 kPa 条件下， 反应 45.0h， 生成 methyl (R)-3-hydroxy-15-methyl-hexadecanoate
  参考文献：
  名称：

  短短的全合成硫氧还蛋白A

  摘要：

  描述了von Willebrand因子受体拮抗剂磺基巴辛A的全合成。短途生产硫磺霉素A的关键步骤包括钌催化的不对称氢化反应和非对映选择性亲电子胺化反应，以构建三个立体异构中心。

  DOI：

  10.1016/s0040-4039(03)01600-9

文献信息

• Synthetic tetra-acylated derivatives of lipid A from Porphyromonas gingivalis are antagonists of human TLR4
  作者：Yanghui Zhang、Jidnyasa Gaekwad、Margreet A. Wolfert、Geert-Jan Boons

  DOI：10.1039/b809090d

  日期：——

  Tetra-acylated lipid As derived from Porphyromonas gingivalis LPS have been synthesized using a key disaccharide intermediate functionalized with levulinate (Lev), allyloxycarbonate (Alloc) and anomeric dimethylthexylsilyl (TDS) as orthogonal protecting groups and 9-fluorenylmethoxycarbamate (Fmoc) and azido as amino protecting groups. Furthermore, an efficient cross-metathesis has been employed for the preparation of the unusual branched R-(3)-hydroxy-13-methyltetradecanic acid and (R)-3-hexadecanoyloxy-15-methylhexadecanoic acid of P. gingivalislipid A. Biological studies have shown that the synthetic lipid As cannot activate human and mouse TLR2 and TLR4 to produce cytokines. However, it has been found that the compounds are potent antagonist of cytokine secretion by human monocytic cells induced by enteric LPS.

  来自牙龈卟啉单胞菌LPS的四酰化脂质A已通过使用关键的二糖中间体合成，该中间体功能化带有乙酰丙酸酯（Lev）、烯丙氧基碳酸酯（Alloc）和异头二甲基苯基硅烷（TDS）作为正交保护基团，以及9-芴甲氧基羰酰胺（Fmoc）和叠氮基作为氨基保护基团。此外，已采用高效的交叉复分解反应制备了牙龈卟啉单胞菌脂质A中不寻常的分支R-(3)-羟基-13-甲基十四烷酸和(R)-3-十六烷酰氧基-15-甲基十六烷酸。生物学研究显示，合成脂质A不能激活人体和小鼠的TLR2和TLR4以产生细胞因子。然而，研究发现这些化合物是肠道LPS诱导的人单核细胞分泌细胞因子的强效拮抗剂。
• SYNTHETIC LIPID A DERIVATIVE
  申请人：Boons Geert-Jan

  公开号：US20100221269A1

  公开（公告）日：2010-09-02

  The invention provides functionalized monosaccharides and disaccharides suitable for use in synthesizing a lipid A derivative, as well as methods for synthesizing and using a synthetic lipid A derivative.

  这项发明提供了适用于合成脂多糖A衍生物的功能化单糖和双糖，以及合成和使用合成脂多糖A衍生物的方法。
• Sulfobacins A and B, Novel von Willebrand Factor Receptor Antagonists. II. Structural Elucidaffon.
  作者：TSUTOMU KAMIYAMA、TAKAYUKI UMINO、YOSHIKO ITEZONO、YUMIKO NAKAMURA、TOMOKO SATOH、KAZUTERU YOKOSE

  DOI：10.7164/antibiotics.48.929

  日期：——

  Sulfobacins A and B are novel von Willebrand factor (vWF) receptor antagonists produced by Chryseobacterium sp. NR 2993. The structures of sulfobacins A and B have been determined to be (2R, 3R)-3-hydroxy-2[(R)-3-hydroxy-15-methylhexadecanamido]-15-methylhexadecanesulfonic acid and (2R, 3R)-3-hydroxy-15-methyl-2-[13-methyltetradecanamido]-hexadecanesulfonic acid, respectively, by various 2D NMR experiments and by methanolysis. The absolute configurations of the sulfobacins were determined by a modified MOSHER'S method. The structures are related to sulfonolipids, major components of the cell envelope of gliding bacteria of the genus Cytophaga.

  硫杆菌素 A 和 B 是由 Chryseobacterium sp. NR 2993 产生的新型 von Willebrand 因子（vWF）受体拮抗剂。通过各种二维核磁共振实验和甲醇分解法，确定了磺酸素 A 和 B 的结构分别为(2R, 3R)-3-羟基-2-[(R)-3-羟基-15-甲基十六酰胺基]-15-甲基十六烷磺酸和(2R, 3R)-3-羟基-15-甲基-2-[13-甲基十四酰胺基]-十六烷磺酸。磺酸苷的绝对构型是通过改进的 MOSHER'S 方法确定的。这些结构与细胞噬菌属滑行细菌细胞包膜的主要成分--磺脂有关。
• Structural Identification of Antibacterial Lipids from Amazonian Palm Tree Endophytes through the Molecular Network Approach
  作者：Morgane Barthélemy、Nicolas Elie、Léonie Pellissier、Jean-Luc Wolfender、Didier Stien、David Touboul、Véronique Eparvier

  DOI：10.3390/ijms20082006

  日期：——

  A library of 197 endophytic fungi and bacteria isolated from the Amazonian palm tree Astrocaryum sciophilum was extracted and screened for antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Four out of five antibacterial ethyl acetate extracts were also cytotoxic for the MRC-5 cells line. Liquid chromatography coupled to tandem mass spectrometry (UPHLC-HRMS/MS) analyses combined with molecular networking data processing were carried out to allow the identification of depsipeptides and cyclopeptides responsible for the cytotoxicity in the dataset. Specific ion clusters from the active Luteibacter sp. extract were also highlighted using an MRSA activity filter. A chemical study of Luteibacter sp. was conducted leading to the structural characterization of eight fatty acid exhibiting antimicrobial activity against MRSA in the tens of µg/mL range.

  从亚马逊棕榈树Astrocaryum sciophilum中分离出的197株内生真菌和细菌库被提取并筛选其对甲氧西林耐药金黄色葡萄球菌（MRSA）的抗菌活性。其中五个抗菌乙酸乙酯提取物中有四个对MRC-5细胞系也具有细胞毒性。采用液相色谱-高分辨质谱（UPHLC-HRMS/MS）分析，结合分子网络数据处理，可确定引起数据集细胞毒性的依赖肽和环肽。利用MRSA活性过滤器，还突出了活性Luteibacter sp.提取物中的特定离子簇。对Luteibacter sp.的化学研究导致了8种脂肪酸的结构表征，这些脂肪酸在十几微克/毫升的范围内对MRSA具有抗菌活性。
• [EN] GLYCOSPHINGOLIPIDS FOR USE IN MODULATING IMMUNE RESPONSES<br/>[FR] GLYCOSPHINGOLIPIDES UTILES À LA MODULATION DES RÉPONSES IMMUNITAIRES
  申请人：UNIV CALIFORNIA

  公开号：WO2013119857A1

  公开（公告）日：2013-08-15

  Provided herein are sphingolipid compounds that are useful for activating natural killer T cells. Also provided are methods for treating or preventing a disease or disorder that is treatable by activating the immune system by stimulating natural killer T cells. The compounds are therefore useful for treating or reducing the likelihood of occurrence of an immune diseases and disorders, such as autoimmune diseases or disorders. The compounds may also be used for treating or reducing the likelihood of occurrence of a microbial infection or for treating or reducing the likelihood of occurrence of a cancer in a subject by administering the sphingolipid compounds described herein.

  本文提供了可用于激活自然杀伤T细胞的鞘脂化合物。同时，还提供了通过刺激自然杀伤T细胞激活免疫系统来治疗或预防可治疗的疾病或疾病的方法。因此，这些化合物可用于治疗或减少免疫性疾病和疾病的发生可能性，如自身免疫性疾病或疾病。这些化合物也可用于通过给予所述鞘脂化合物来治疗或减少受试者微生物感染的可能性或治疗或减少受试者癌症发生的可能性。