(ethyl carbonic) (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic anhydride | 85954-18-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (ethyl carbonic) (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic anhydride
• CAS: 85954-18-3
• 化学式: C₂₇H₄₄O₇
• 分子量: 480.642
• InChiKey: AJXGWNZKLVNAGS-ZESNAWOTSA-N

物化性质

• 沸点：
  594.7±60.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  113.29
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (ethyl carbonic) (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic anhydride 在 palladium diacetate 、 tricyclohexylphosphine tetrafluoroborate 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 34.0h， 生成 ethyl 24a,24b,24c-trihomocholanoate-3,7,12,24-tetrone
  参考文献：
  名称：

  Pd(OAc)2/四氟硼酸磷催化 Fukuyama 偶联反应高效合成 γ-氧代羧酸酯和同位素标记的 5-氨基乙酰丙酸 (5-ALA)

  摘要：

  Pd(OAc) 2 /四氟硼酸磷有效催化福山与对甲苯基硫酯和 3-乙氧基-3-氧代丙基溴化锌的偶联反应，在温和条件下提供γ-氧代羧酸酯。Pd(OAc) 2 /PCy 3 ·HBF 4是最有效的催化剂，提供了一种以易得的羧酸为起始原料高效合成功能化γ-氧代酯的直接方法。利用优化条件，高效合成了同位素标记的 5-氨基乙酰丙酸 (( 15 N)-5-ALA)。

  DOI：

  10.1016/j.tetlet.2023.154570
• 作为产物：
  描述：

  胆酸 、 氯甲酸乙酯 在 三乙胺 作用下， 反应 0.5h， 生成 (ethyl carbonic) (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic anhydride
  参考文献：
  名称：

  胆汁酸烷基酰胺的超分子凝胶化特性的系统调节

  摘要：

  详细研究了九种基于胆酸烷基酰胺的低分子量胶凝剂（LMWG）的自组装性能。基于该结果，尽管脂族侧链的性质也调节了凝胶化能力，但是连接至甾族骨架的羟基数目在凝胶化中起着重要作用。在研究的50种凝胶体系中，有35种基于石胆酸，而15种基于胆酸衍生物。脱氧胆酸衍生物没有形成任何凝胶。凝胶化主要发生在芳族溶剂中，并且凝胶表现出典型的纤维或球形形态。在13在结晶材料和相应的湿有机凝胶上测得的C交叉极化魔角旋转（CPMAS）NMR光谱是相似的，这表明两种材料中发现的化学环境（即分子间相互作用）相似。研究的所有九种胆酸酰胺衍生物的单晶X射线结构揭示了固态中非常相似的分子构象，并洞悉了凝胶态下可能的分子间相互作用。

  DOI：

  10.1002/chem.201803151

文献信息

• Synthesis of nucleoside and nucleotide conjugates of bile acids, and polymerase construction of bile acid-functionalized DNA
  作者：Satu Ikonen、Hana Macíčková-Cahová、Radek Pohl、Miloslav Šanda、Michal Hocek

  DOI：10.1039/b924072a

  日期：——

  Sonogashira cross-coupling reactions of 5-iodopyrimidine or 7-iodo-7-deazaadenine nucleosides with bile acid-derived terminal acetylenes linked via an ester or amide tether gave the corresponding bile acid–nucleoside conjugates. Analogous reactions of halogenated nucleoside triphosphates gave directly bile acid-modified dNTPs. Enzymatic incorporation of these modified nucleotides to DNA was successfully

  Sonogashira的水交叉偶联反应 5-碘嘧啶带有胆汁酸衍生的末端乙炔的7-iodo-7-deazaadenine核苷通过酯或酰胺系链连接在一起，得到了相应的胆汁酸-核苷共轭物。卤代核苷三磷酸的类似反应直接得到胆汁酸修饰的dNTP。使用Phusion聚合酶进行引物延伸，成功地将这些修饰的核苷酸酶促掺入DNA。dNTP之一（dCTP 轴承 胆酸）对于PCR扩增也是有效的。
• [EN] PROCESS FOR THE PREPARATION OF CHOLYL-L-LYSINE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE CHOLYL-L-LYSINE
  申请人：NORGINE BV

  公开号：WO2010092381A1

  公开（公告）日：2010-08-19

  A process for the preparation of cholyl-L-lysine comprising the steps of:- (a) reacting N-ε-CBZ-cholyl-L-lysine with a hydrogen source in the presence of a catalyst in a solvent comprising one or more alkanols; (b) removing the catalyst; (c) optionally diluting the resulting reaction mixture with water and optionally adjusting the pH of the resultant reaction mixture to a pH less than or equal to about 4; (d) removing the bulk of the alkanol whilst ensuring that the alkanol content of the resultant mixture is maintained above about 3% w/w of the remaining mixture; (e) extracting the resultant mixture from step (d) with an organic solvent; (f) adjusting the pH of the aqueous layer to a pH of about 4.5 or greater to precipitate cholyl-L-lysine; (g) isolate the precipitate.

  一种制备胆酰-L-赖氨酸的方法，包括以下步骤：(a) 在存在催化剂的溶剂中，将N-ε-CBZ-胆酰-L-赖氨酸与氢源反应，所述溶剂包含一种或多种烷醇；(b) 去除催化剂；(c) 可选地用水稀释所得的反应混合物，并可选地将所得的反应混合物的pH调整至小于或等于约4；(d) 去除大部分烷醇，同时确保所得混合物中烷醇含量保持在剩余混合物的约3% w/w以上；(e) 用有机溶剂从步骤(d)中提取所得混合物；(f) 将水层的pH调整至约4.5或更高以沉淀出胆酰-L-赖氨酸；(g) 分离沉淀物。
• Self-assembly properties of bile acid derivatives of <scp>l</scp>-cysteine, <scp>l</scp>-valine and <scp>l</scp>-serine alkyl esters
  作者：Virpi Noponen、Arto Valkonen、Manu Lahtinen、Hannu Salo、Elina Sievänen

  DOI：10.1080/10610278.2012.735365

  日期：2013.3.1

  Comprehensive self-assembly studies for nine bile acid amides of amino acid esters are reported. The number of the hydroxyl groups attached to the steroidal skeleton and the character of the amino acid ester moiety were used as variables when examining the self-assembly properties of the compounds. Two of the compounds were shown to undergo self-assembly leading to organogelation. In addition, preliminary

  报告了氨基酸酯的九种胆汁酸酰胺的综合自组装研究。在检查化合物的自组装特性时，将连接到甾体骨架上的羟基数量和氨基酸酯部分的特征用作变量。其中两种化合物显示出自组装导致有机凝胶化。此外，在极性有机溶剂的水性混合物中进行了初步自组装研究。为了更深入地了解自组装结构，使用了显微方法（光学显微镜和扫描电子显微镜）。此外，解决了三种化合物的单晶 X 射线结构。
• Fluorogenic substrates and pre‐column derivatization for monitoring the activity of bile salt hydrolase from Clostridium perfringens
  作者：Tim Keuler、Valentina Wolf、Carina Lemke、Rabea Voget、Annett Braune、Michael Gütschow

  DOI：10.1016/j.bioorg.2023.106574

  日期：2023.9

  to the diversity of bile acids. There has been great interest in surveying BSH activity. We compared two substrates with either 2-(7-amino-4-methyl-coumarinyl)acetic acid or 7-amino-4-methyl-coumarin as fluorescent reporters of BSH activity. The BSH-catalyzed conversion of the natural substrate taurocholic acid was followed through an HPLC-based assay by applying 7-nitrobenzo[c][1,2,5]oxadiazole as

  胆汁酸库对人类健康和疾病有着深远的影响。肠道微生物群通过细菌胆汁盐水解酶 (BSH) 催化的关键第一步启动结合胆汁酸的代谢，并对胆汁酸的多样性做出独特的贡献。人们对调查博西家电的活动表现出了浓厚的兴趣。我们比较了两种底物，其中 2-(7-氨基-4-甲基-香豆素基)乙酸或 7-氨基-4-甲基-香豆素作为 BSH 活性的荧光报告基因。通过使用 7-硝基苯并[ c ][1,2,5]恶二唑作为酶促反应中释放的牛磺酸清除剂，通过基于 HPLC 的测定来跟踪 BSH 催化的天然底物牛磺胆酸的转化。因此，引入了监测胆盐水解酶活性的新机会。
• Bile acid–cysteamine conjugates: Structural properties, gelation, and toxicity evaluation
  作者：Virpi Noponen、Heini Belt、Manu Lahtinen、Arto Valkonen、Hannu Salo、Jitka Ulrichová、Adéla Galandáková、Elina Sievänen

  DOI：10.1016/j.steroids.2011.11.006

  日期：2012.2

  Design, synthesis, and characterization of six novel bile acid-cysteamine conjugates together with investigation of their structural studies, gelation properties, and preliminary toxicity evaluation, are reported. Solid state properties of selected compounds were studied by means of X-ray diffraction and C-13 CPMAS NMR spectroscopy. N-(2-thioethyl)-3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholan-24-amide was shown to exhibit (pseudo)polymorphism, and a single crystal structure of its non-stoichiometric hydrate is reported herein. Cholyl and dehydrocholyl derivatives bearing three functionalities in their steroidal backbone were shown to undergo self-assembly leading to gelation in certain organic solvents. Preliminary morphology studies of the formed gels by scanning electron microscopy (SEM) were performed. The standard model mouse fibroblast cell line together with the MTT and NR tests were utilized for evaluating the toxicity of the prepared compounds. Lithocholyl, ursodeoxycholyl, and dehydrocholyl derivatives turned out to be relatively non-toxic in the conditions studied. (C) 2011 Elsevier Inc. All rights reserved.