pentafluorophenol octadecanoate | 139122-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: pentafluorophenol octadecanoate
• 英文别名: perfluorophenyl stearate；Pentafluorophenyl octadecanoate；(2,3,4,5,6-pentafluorophenyl) octadecanoate
• CAS: 139122-40-0
• 化学式: C₂₄H₃₅F₅O₂
• 分子量: 450.533
• InChiKey: VCERHYWMYNSHSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  451.3±45.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  31
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  pentafluorophenol octadecanoate 在 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成
  参考文献：
  名称：

  [EN] ENDOSOMAL ESCAPE DOMAINS FOR DELIVERY OF MACROMOLECULES INTO CELLS
  [FR] DOMAINES D'ÉCHAPPEMENT ENDOSOMAL POUR INTRODUIRE DES MACROMOLÉCULES DANS DES CELLULES

  摘要：

  本公开提供了包含通用内体逃逸结构域的化合物和组合物，以及它们的应用，包括将大分子递送到细胞中。

  公开号：

  WO2022081589A1
• 作为产物：
  描述：

  三氟乙酸五氟苯酯 、 硬脂酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 pentafluorophenol octadecanoate
  参考文献：
  名称：

  脂肪酸结合增强了肌肉中反义寡核苷酸的效力。

  摘要：

  增强肌肉中反义寡核苷酸（ASO）的功能吸收将有助于开发针对肌肉中表达的基因的ASO治疗药物。我们假设改善白蛋白结合将促进ASO从血液腔室到肌肉组织间质的遍历，从而增强ASO功能的吸收。我们合成了具有一定疏水性的结构多样的饱和和不饱和脂肪酸共轭ASO。ASO脂肪酸缀合物与血浆蛋白的结合亲和力随脂肪酸链长度的增加而改善，而对于包含16至22个碳原子脂肪酸链长度的ASO缀合物，则观察到最高的结合亲和力。双键的不饱和度或构象度似乎对ASO脂肪酸缀合物的蛋白质结合或活性没有影响。脂肪酸ASO共轭物的活性与对白蛋白的亲和力相关，最紧密的白蛋白结合剂在肌肉中表现出最高的活性改善。棕榈酸结合增加了ASO血浆Cmax，并改善了ASO向小鼠肌肉间隙的传递。棕榈酸的缀合可改善小鼠肌肉中DMPK，Cav3，CD36和Malat-1 ASO的效力（3至7倍）。我们的方法为开发针对肌肉疾病的更有效的治疗性ASO提供了

  DOI：

  10.1093/nar/gkz354

文献信息

• 基于Kdo的糖脂衍生物及其制备和抗菌应用
  申请人：陕西师范大学

  公开号：CN112679456B

  公开（公告）日：2022-12-27

  本发明公开了一种基于Kdo的糖脂衍生物及其制备和抗菌应用，所述衍生物的结构式为：式中R1为脂肪族氨基(即CH3(CH2)nNH‑，n＝1～17)，R2＝‑NH3+Cl‑；或者R1为‑OH或‑O‑NH4+，R2为RCONH‑(R为C1～18的饱和或者不饱和烷基)。本发明中的糖脂与已报道的糖脂相比，是基于革兰式阴性菌来源的重要单糖Kdo(3‑脱氧‑D‑甘露‑2‑辛酮糖酸)制备的非天然糖脂类化合物，该类化合物可作为新型的抗菌物质。
• Quantitative Measurements of Recombinant HIV Surface Glycoprotein 120 Binding to Several Glycosphingolipids Expressed in Planar Supported Lipid Bilayers
  作者：John C. Conboy、Katherine D. McReynolds、Jacquelyn Gervay-Hague、S. Scott Saavedra

  DOI：10.1021/ja011225s

  日期：2002.2.1

  The interaction of recombinant HIV-1 surface glycoprotein gp120 (rgp120) with natural isolates of lactosylceramide (LacCer), glucosylceramide (GlcCer), and galactosylceramide (GaiCer) has been quantitatively measured under equilibrium conditions using total internal reflection fluorescence (TIRF) spectroscopy. The binding affinity (K-a) of rgp120 to these glycosphingolipids (GSLs), reconstituted at 5 mol % in supported planar lipid bilayers composed of 95 mol % POPC, is ca. 10(6) M-1 for dissolved rgp120 concentrations greater than 25 nM. In contrast, at concentrations of rgp120 between 0.2 and 15 nM, rgp120 does not bind significantly to LacCer and GlcCer, but has a high affinity for GalCer with a measured K-a value of 1.6 x 10(9) M-1. However, protein surface coverage measurements show that this strong binding process accounts for very little of the total protein adsorbed over the entire concentration range studied. At a protein concentration of ca. 20 nM, the surface coverage is only 3% of that achieved at apparent saturation (i.e., when the protein concentration is ca. 220 nM). Thus the "high affinity" binding sites comprise only a small fraction of the total number of binding sites. Several other variables were investigated, Rgp120 binding behavior at membranes doped with alpha-hydroxygalactosylceramide (alpha-GalCer) was very similar to that observed with GalCer, showing that the presence/absence of an alpha-hydroxy moiety does not significantly affect galactosylceramide recognition. Phase segregation of GalCer, which occurs when the mole fraction of this GSL in a POPC bilayer exceeds ca. 0.1, was also investigated and showed no effect on binding affinity at low rgp120 concentrations. To investigate the influence of fatty acid chain length, GSLs with monodisperse C-18 and C-24 chain lengths, both with and without an alpha-hydroxy moiety, were synthesized, and their binding affinity to rgp120 was examined. Relative to the natural isolates (which contain a mixture of chain lengths), minimal differences were observed; thus among the compounds tested, fatty acid chain length does not affect GSL recognition. The results of this work should aid efforts to design anti-HIV-1 agents based on membrane-tethered, carbohydrate-based receptors for rgp120.
• Antibiotics GE23077, novel inhibitors of bacterial RNA polymerase. Part 3: Chemical derivatization
  作者：Riccardo Mariani、Giorgio Granata、Sonia I. Maffioli、Stefania Serina、Cristina Brunati、Margherita Sosio、Alessandra Marazzi、Alfredo Vannini、Dinesh Patel、Richard White、Romeo Ciabatti

  DOI：10.1016/j.bmcl.2005.05.060

  日期：2005.8

  GE23077 is a novel RNA polymerase inhibitor that is isolated from the fermentation broth of an Actinomadura sp. It is a cyclic heptapeptide complex made up of four factors, differing in the structure of acyl group connected to the side chain of an alpha,beta-diaminopropanoic acid moiety and in the configuration of the stereocenter of an alpha-amino-malonic acid residue. Although GE23077 shows strong inhibitory activity on both Rifampicin-sensitive and -resistant polymerases, it exhibits poor antimicrobial activity. The most reasonable explanation for this property has been based on the lack of penetration of the molecule across the bacterial membrane, owing to its strong hydrophilic character. To improve penetration, several parts of the molecule were accordingly modified with the aim of altering the physico-chemical properties of GE23077. The current SAR study has identified moieties important for RNA polymerase activity. (c) 2005 Elsevier Ltd. All rights reserved.
• MACROCYCLIC PEPTIDES USEFUL AS IMMUNOMODULATORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP3218392B1

  公开（公告）日：2020-07-29
• Fatty acid conjugation enhances potency of antisense oligonucleotides in muscle
  作者：Thazha P Prakash、Adam E Mullick、Richard G Lee、Jinghua Yu、Steve T Yeh、Audrey Low、Alfred E Chappell、Michael E Østergaard、Sue Murray、Hans J Gaus、Eric E Swayze、Punit P Seth

  DOI：10.1093/nar/gkz354

  日期：2019.7.9

  structurally diverse saturated and unsaturated fatty acid conjugated ASOs with a range of hydrophobicity. The binding affinity of ASO fatty acid conjugates to plasma proteins improved with fatty acid chain length and highest binding affinity was observed with ASO conjugates containing fatty acid chain length from 16 to 22 carbons. The degree of unsaturation or conformation of double bond appears to have

  增强肌肉中反义寡核苷酸（ASO）的功能吸收将有助于开发针对肌肉中表达的基因的ASO治疗药物。我们假设改善白蛋白结合将促进ASO从血液腔室到肌肉组织间质的遍历，从而增强ASO功能的吸收。我们合成了具有一定疏水性的结构多样的饱和和不饱和脂肪酸共轭ASO。ASO脂肪酸缀合物与血浆蛋白的结合亲和力随脂肪酸链长度的增加而改善，而对于包含16至22个碳原子脂肪酸链长度的ASO缀合物，则观察到最高的结合亲和力。双键的不饱和度或构象度似乎对ASO脂肪酸缀合物的蛋白质结合或活性没有影响。脂肪酸ASO共轭物的活性与对白蛋白的亲和力相关，最紧密的白蛋白结合剂在肌肉中表现出最高的活性改善。棕榈酸结合增加了ASO血浆Cmax，并改善了ASO向小鼠肌肉间隙的传递。棕榈酸的缀合可改善小鼠肌肉中DMPK，Cav3，CD36和Malat-1 ASO的效力（3至7倍）。我们的方法为开发针对肌肉疾病的更有效的治疗性ASO提供了