N-cholyl-γ-aminobutyrate | 89311-02-4

• 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: N-cholyl-γ-aminobutyrate
• 英文别名: 3-[(3α,7α,12α-trihydroxy-24-oxo-5β-cholan-24-yl)amino]propanecarboxylic acid；4-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]butanoic acid
• CAS: 89311-02-4
• 化学式: C₂₈H₄₇NO₆
• 分子量: 493.684
• InChiKey: SJSVGOMSHKDZBO-VVHBOOHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-cholyl-γ-aminobutyrate 、 5,11,17,23-tetraamino-25,26,27,28-tetra(hexyloxy)calix[4]arene 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以36%的产率得到(4R)-N-[4-oxo-4-[[25,26,27,28-tetrahexoxy-11,17,23-tris[4-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]butanoylamino]-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]amino]butyl]-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanamide
  参考文献：
  名称：

  Solvent-Induced Amphiphilic Molecular Baskets:  Unimolecular Reversed Micelles with Different Size, Shape, and Flexibility

  摘要：

  Amphiphilic molecular baskets were obtained by attaching facially amphiphilic cholate groups to a covalent scaffold (calix[4] arene or 1,3,5-2,4,6-hexasubstituted benzene). In a solvent mixture consisting of mostly a nonpolar solvent (i.e., CCl4) and a polar solvent (i.e., DMSO), the hydrophilic faces of cholates turned inward to form a reversed-micelle-like conformer whose stability was strongly influenced by the number of the cholates and the topology of the scaffold. Preferential solvation of the hydrophilic faces of cholates within the molecule by the polar solvent was cooperative and gave the fundamental driving force to the conformational change. The reversed-micelle-like conformer was most stable in structures that allowed multiple cholates to form a microenvironment that could efficiently enrich the polar solvent molecules from the bulk solvent mixture.

  DOI：

  10.1021/jo0607663
• 作为产物：
  描述：

  cholic acid N-succinimidyl ester 、 4-氨基丁酸 在 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 以49.5%的产率得到N-cholyl-γ-aminobutyrate
  参考文献：
  名称：

  Solvent-Induced Amphiphilic Molecular Baskets:  Unimolecular Reversed Micelles with Different Size, Shape, and Flexibility

  摘要：

  Amphiphilic molecular baskets were obtained by attaching facially amphiphilic cholate groups to a covalent scaffold (calix[4] arene or 1,3,5-2,4,6-hexasubstituted benzene). In a solvent mixture consisting of mostly a nonpolar solvent (i.e., CCl4) and a polar solvent (i.e., DMSO), the hydrophilic faces of cholates turned inward to form a reversed-micelle-like conformer whose stability was strongly influenced by the number of the cholates and the topology of the scaffold. Preferential solvation of the hydrophilic faces of cholates within the molecule by the polar solvent was cooperative and gave the fundamental driving force to the conformational change. The reversed-micelle-like conformer was most stable in structures that allowed multiple cholates to form a microenvironment that could efficiently enrich the polar solvent molecules from the bulk solvent mixture.

  DOI：

  10.1021/jo0607663

文献信息

• Reducing Risk of Contracting Clostridium-Difficile Associated Disease
  申请人：The Regents of the Nevada System of Higher Education on behalf of the University of Neveda

  公开号：US20140045808A1

  公开（公告）日：2014-02-13

  A method of treating a patient to reduce risk of developing Clostridium difficile -associated disease or reducing existing Clostridium difficile -associated disease in a mammalian subject involves administering to a mammalian subject an effective amount of a germination-inhibiting compound derived from taurocholate. Novel compounds of this class are also provided.

  治疗患者以减少发生梭菌类难辨梭菌相关疾病的风险或减少哺乳动物主体中已存在的梭菌类难辨梭菌相关疾病的方法涉及向哺乳动物主体投入源自牛磺胆酸的抑制萌发化合物的有效量。此类新颖化合物也提供。
• Synthesis and spectroscopic analysis of modified bile salts
  作者：Annie M. Ballatore、Carl F. Beckner、Richard M. Caprioli、Neville E. Hoffman、Joachim G. Liehr

  DOI：10.1016/0039-128x(83)90007-7

  日期：1983.2

  intensity molecular ions. The purity of the products and their molecular weights were checked by a novel ionization technique in mass spectrometry, fast atom bombardment (FAB) mass spectrometry. FAB spectra were obtained from underivatized bile salts. The spectra were characterized by ions formed by attachment of a proton or an alkali ion to the bile salt to give intense M+H, M+Na, or M+K ions, which then

  为了研究体内肝胆汁酸的转运，合成了一系列修饰的胆汁盐。由胆酸，氯甲酸乙酯和相应的氨基酸制备L-亮氨酸，L-丙氨酸，D-丙氨酸，β-丙氨酸，L-脯氨酸和γ-氨基丁酸的N-胆酰基衍生物。产物的结构分析主要通过甲酯/乙酸酯衍生物的电子冲击质谱法（20eV）进行。在所有EI光谱中，较低质量区域中的碎片包括酰胺键附近的McLafferty重排离子（β裂解）和γ裂解的产物离子。在质量较高的区域，碎片化的特征是从低强度分子离子中连续去除乙烯酮和/或乙酸。通过质谱中的新型电离技术，快速原子轰击（FAB）质谱法检查了产物的纯度及其分子量。FAB光谱从未衍生的胆汁盐获得。光谱的特征是通过将质子或碱金属离子附着在胆汁盐上形成离子，从而产生强烈的M + H，M + Na或M + K离子，然后显示出很少的碎片。
• US9079935B2
  申请人：——

  公开号：US9079935B2

  公开（公告）日：2015-07-14