(E,E)-法呢基硫醇 | 138077-74-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (E,E)-法呢基硫醇
• 英文名称: trans,trans-farnesyl mercaptan
• 英文别名: farnesyl thiol；(2E,6E)-3,7,11-trimethyldodeca-2,6,10-triene-1-thiol；farnesyl mercaptan
• CAS: 138077-74-4
• 化学式: C₁₅H₂₆S
• 分子量: 238.437
• InChiKey: CJWPDADGDASKGI-YFVJMOTDSA-N

物化性质

• 沸点：
  334.0±21.0 °C(Predicted)
• 密度：
  0.881±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E,E)-法呢基硫醇 在 正丁基锂 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.34h， 生成 S-methyl S-(farnesylthio)acetothiohydroximate
  参考文献：
  名称：

  Structure-activity studies on the retinal rod outer segment isoprenylated protein methyltransferase

  摘要：

  Structure-activity studies were performed on the retinal rod outer segment isoprenylated protein methyltransferase that transfers a methyl group from S-adenosylmethionine (AdoMet) to the carboxyl group of isoprenylated (farnesylated or geranylgeranylated) cysteine residues. This methyltransferase enzyme has been shown to methylate N-acetyl-S-farnesyl-L-cysteine (L-AFC, 1) and S-(farnesyl-3-thio)propionic acid (FTP, 2). It is shown here that the enzyme does not enzymatically process D-AFC (8), although D-AFC (8) is a mixed-type inhibitor of the enzyme. Small modifications in the FTP (2) structural series generally lead to inactive substrates. For example, neither the cis- nor the trans-acrylate derivatives of FTP (2) are substrates of the enzyme, but both are inhibitors of it. Alkyl substitutions at the 3-position of FTP (2), moreover, lead to inhibitors of the methyltransferase. Substituents at the 2-position of FTP (2), as in 2-methyl-S-(farnesyl-3-thio)propionic acid (MFTP, 28) or S-farnesyl-2-(thiomethyl)acrylic acid (FTMA, 31), produce active substrates. Modifications at the carboxyl moiety produce neither substrates nor inhibitors of the enzyme. The conclusion from this and earlier studies is that the methyltransferase is selective for an isoprenylated thiopropionate moiety. Small deviations from this minimally essential structure lead to the abolition of substrate activity.

  DOI：

  10.1021/ja00036a052
• 作为产物：
  描述：

  反式,反式-金合欢醇 在 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (E,E)-法呢基硫醇
  参考文献：
  名称：

  Antiparasitic Activity of Sulfur- and Fluorine-Containing Bisphosphonates against Trypanosomatids and Apicomplexan Parasites

  摘要：

  基于2-烷基（氨基）乙基-1,1-双膦酸酯与克鲁兹锥虫法尼基二磷酸合成酶的晶体学数据，设计、合成了一些线性1,1-双膦酸及其他密切相关的衍生物，并对其在针对克鲁兹锥虫（造成查加斯病的病原体）和弓形虫（造成弓形虫病的病原体）的生物活性进行了评估，同时也针对克鲁兹锥虫（TcFPPS）和弓形虫（TgFPPS）的目标酶法尼基焦磷酸合成酶进行评估。含异戊烯基的1,1-双膦酸酯表现出适度的抗寄生虫活性，而线性α-氟-2-烷基（氨基）乙基-1,1-双膦酸酯则出人意料地缺乏抗寄生虫活性。尽管未表现出有效的抗寄生虫活性，这些数据对于建立结构活性关系却显得非常重要。

  DOI：

  10.3390/molecules22010082

文献信息

• Facile triflic acid-catalyzed α-1,2-<i>cis</i>-thio glycosylations: scope and application to the synthesis of<i>S</i>-linked oligosaccharides, glycolipids, sublancin glycopeptides, and T_N/T_Fantigens
  作者：Sanyong Zhu、Ganesh Samala、Eric T. Sletten、Jennifer L. Stockdill、Hien M. Nguyen

  DOI：10.1039/c9sc04079j

  日期：——

  access α-1,2-cis-S-linked glycosides using triflic acid as a catalyst to promote the glycosylation of a series of thiols with D-glucosamine, galactosamine, glucose, and galactose electrophiles. This method is broadly applicable for the stereoselective synthesis of S-linked glycopeptides, oligosaccharides and glycolipids in high yield and excellent α-selectivity. Many of the synthetic limitations associated

  由于S-连接的糖缀合物具有比O-糖苷对应物更高的化学稳定性和酶抗性，因此引起了越来越多的研究兴趣。我们在此报告了一种简便的方法，该方法使用三氟甲磺酸作为催化剂来促进α-1,2-顺式S连接的糖苷，以促进一系列硫醇与D-葡萄糖胺，半乳糖胺，葡萄糖和半乳糖亲电试剂的糖基化。该方法广泛适用于以高产率和优异的α-选择性立体合成S-连接的糖肽，寡糖和糖脂。与这些S的制备有关的许多合成限制该催化方法克服了连接产物。
• Hypocholesterolemic unsymmetrical dithiol ketals
  申请人：Bristol-Myers Squibb Company

  公开号：US05321046A1

  公开（公告）日：1994-06-14

  Disclosed herein are novel unsymmetrical dithiol ketals which are useful in the treatment or prevention of hypercholesterolemia, hyperlipoproteinemia, and atherosclerosis.

  本文披露了一种新型的不对称二硫醇醚酮，可用于治疗或预防高胆固醇血症、高脂蛋白血症和动脉粥样硬化。
• Synthesis of prenylated cysteines from serine derivatives
  作者：William W. Epstein、Zhaolin Wang

  DOI：10.1039/a700428a

  日期：——

  Prenylated cysteines are prepared by the reaction of serineβ-lactone with prenyl thiolate.

  卤代半胱氨酸是通过丝氨酸β-内酯与卤代硫酸酯反应制备的。
• INHIBITORS OF POLYISOPRENYLATED METHYLATED PROTEIN METHYL ESTERASE
  申请人：Lamango Nazarius Saah

  公开号：US20090253640A1

  公开（公告）日：2009-10-08

  Inhibitors of the enzyme prenylated methylated protein methyl esterase (PMPMEase), the last step in the prenylation process for many eukaryotic proteins, having the general structure R 1 -X-A-B(R 2 )-Y or R 1 -X-A(R 2 )-B-Y, where R 1 is preferably a polyisoprenyl group, X is a linking group, Y is a group that promotes affinity interactions to the active site of PMPMEase and imparts hydrolysis resistance to the inhibitor, A and B are bridge atoms, and R 2 is a characteristic-providing substituent.

  抑制酶前醇基化蛋白甲基酯酶（PMPMEase）的化合物，这是许多真核蛋白质前醇化过程的最后一步，具有一般结构R1-X-A-B（R2）-Y或R1-X-A（R2）-B-Y，其中R1最好是多异戊烯基团，X是连接基团，Y是促进与PMPMEase活性位点的亲和作用并赋予抑制剂水解抗性的基团，A和B是桥接原子，R2是提供特征的取代基。
• Chemical Modification of Proteins
  申请人：Bernardes Goncalo

  公开号：US20110144304A1

  公开（公告）日：2011-06-16

  The invention relates to methods for selectively converting a cysteine residue in a peptide or protein to the dehydroalanine (Dha) residue. The method also works on selenocysteine and substituted cysteine and selenocysteine residues, resulting in the Dha residue which may be converted to any natural or unnatural amino acid residue desired without the alteration of the remainder of the peptide or protein. The invention also allows ligation of a desired peptide at any point rather than at a point where there should be a naturally occurring cysteine, thereby allowing native chemical ligation to be used in the synthesis of peptides that do not contain cysteine. The methodology allows for the synthesis of very large peptides.

  本发明涉及一种将肽或蛋白质中的半胱氨酸残基选择性转化为去氢丙氨酸（Dha）残基的方法。该方法也适用于硒半胱氨酸和取代的半胱氨酸和硒半胱氨酸残基，从而产生Dha残基，该残基可以转化为所需的任何天然或非天然氨基酸残基，而不改变肽或蛋白质的其余部分。本发明还允许在任何点上连接所需的肽，而不是在应该存在天然半胱氨酸的点上进行连接，从而允许在合成不含半胱氨酸的肽时使用天然化学连接。该方法允许合成非常大的肽。