5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-N-(2-(tritylthio)ethyl)pentanamide | 1330059-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-N-(2-(tritylthio)ethyl)pentanamide
• 英文别名: 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-(2-tritylsulfanylethyl)pentanamide
• CAS: 1330059-84-1
• 化学式: C₃₁H₃₅N₃O₂S₂
• 分子量: 545.77
• InChiKey: OGMVLIAARDLREG-YCVJPRETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-N-(2-(tritylthio)ethyl)pentanamide 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以72 %的产率得到N-(2-mercaptoethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide
  参考文献：
  名称：

  通过 Au(III) 聚合物试剂进行高效端基官能化和二嵌段共聚物合成

  摘要：

  在此，我们描述了实验室稳定的有机金属 Au( III ) 封端聚合物试剂的合成。这些试剂介导含硫醇小分子和聚合物的化学选择性S-芳基化，分别产生官能化的单遥爪聚合物和二嵌段共聚物。这些转化在几分钟内快速进行，并在定量转化中产生缀合物，使该策略成为聚合物功能化工具箱的有力补充。

  DOI：

  10.1039/d3cc05350d
• 作为产物：
  描述：

  三苯基甲醇 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-N-(2-(tritylthio)ethyl)pentanamide
  参考文献：
  名称：

  Au(III) 介导的半胱氨酸超快芳基化

  摘要：

  通过机械工作和合理设计，我们开发了最快的有机金属非生物半胱氨酸生物结合。因此，开发的有机金属 Au(III) 生物共轭试剂能够选择性标记低至皮摩尔浓度的 Cys 部分，并允许从肽、蛋白质和寡核苷酸快速构建复杂的异质结构。这项工作展示了有机金属化学如何与生物分子相互作用，并产生一系列经典有机化学工具无法比拟的反应性。

  DOI：

  10.1021/jacs.3c12170

文献信息

• Application of a water-soluble pyridyl disulfide amine linker for use in Cu-free click bioconjugation
  作者：Joshua D. Thomas、Terrence R. Burke

  DOI：10.1016/j.tetlet.2011.06.042

  日期：2011.8

  Described herein is the design and synthesis of a discrete heterobifunctional PEG-based pyridyl disulfide/amine-containing linker that can be used in the Cu-free click preparation of bioconjugates. The title PEG-based pyridyl disulfide amine linker is a potentially useful reagent for preparing water-soluble disulfide-linked cargos, and that it may be particularly valuable in expanding the field of Cu-free click-based bioconjugations to include reductively labile antibody, polymer, or nanoparticle-based drug conjugates. Published by Elsevier Ltd.
• [EN] REACTIVITY-BASED SCREENING FOR NATURAL PRODUCT DISCOVERY<br/>[FR] CRIBLAGE FONDÉ SUR LA RÉACTIVITÉ UTILISABLE EN VUE DE LA DÉCOUVERTE DE PRODUITS NATURELS
  申请人：UNIV ILLINOIS

  公开号：WO2015191789A3

  公开（公告）日：2016-08-11
• Synthesis of Pyridyl Disulfide-Functionalized Nanoparticles for Conjugating Thiol-Containing Small Molecules, Peptides, and Proteins
  作者：André J. van der Vlies、Conlin P. O’Neil、Urara Hasegawa、Nathan Hammond、Jeffrey A. Hubbell

  DOI：10.1021/bc9004443

  日期：2010.4.21

  Previously we reported emulsion polymerization of propylene sulfide with Pluronic F127 as an emulsifier, yielding nanoparticles (NPs) in the 25 nm size range. Immunologically functional NPs were prepared by adding an antigen Pluronic conjugate to the polymerization mixture (Reddy, S. T., et al. (2007) Nat. Biotechnol. 25, 1159). We sought a more flexible scheme for conjugation of antigens and other biomolecules to the NP surfaces that would allow for milder reaction conditions than achievable during the polymerization step. Here, we present the synthesis of such functionalizable NPs in the form of NPs that carry thiol-reactive groups, to which thiol-containing antigens (peptide or protein) or other biomolecules can be conjugated under mild conditions to yield immunofunctional NPs. The Pluronic-stabilized poly(propylene sulfide) (PPS) NPs with thiol-reactive pyridyl disulfide groups are prepared in two steps by (1) emulsion polymerization of propylene sulfide in the presence of a carboxylate-Pluronic and (2) reaction of the carboxylic acid groups on the NP surface with cysteaminc pyridyl disulfide and a water-soluble carbodiimide reagent. We choose pyridyl disulfide groups to have a reduction-sensitive disulfide bond linking the antigen to the NP surface, allowing efficient release of antigen inside the cell in response to the reductive conditions within the endosome. The functionalizable NPs are characterized by proton NMR, dynamic light scattering (DLS), UV/vis spectroscopy, and transmission electron microscopy (TEM). Conjugation of small molecules and protein to the NP surface is presented.
• Synthesis and biological evaluation of molecular probes based on the 9-methylstreptimidone derivative DTCM-glutarimide
  作者：Eisuke Ota、Masatoshi Takeiri、Miyuki Tachibana、Yuichi Ishikawa、Kazuo Umezawa、Shigeru Nishiyama

  DOI：10.1016/j.bmcl.2011.11.045

  日期：2012.1

  Molecular probes based on 3-[(dodecylthiocarbonyl)methyl]glutarimide (DTCM-glutarimide) were synthesized and assessed for inhibitory activity against LPS-induced NO production. Among the probes examined, several derivatives exhibited potential for use in determining the target proteins of DTCM-glutarimide. (C) 2011 Elsevier Ltd. All rights reserved.
• REACTIVITY-BASED SCREENING FOR NATURAL PRODUCT DISCOVERY
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：US20170227545A1

  公开（公告）日：2017-08-10

  A method of identifying a natural product comprising NP—[X] n is provided. The method includes several steps. The first step includes selecting an organism having a biosynthetic pathway for producing the natural product comprising NP—[X] n using a bioinformatics algorithm. The second step includes preparing a sample suspected to contain NP—[X] n including a complex cellular metabolite mixture from an organism. The third step includes reacting the sample suspected to contain NP—[X] n with reactivity probe Y according to Scheme I: Scheme I. NP—[X] n represents a natural product NP having a chemical moiety X that is susceptible to chemical modification by reactivity probe Y to form at least one product adduct NP—[X] n-m [Z] n in which chemical moiety X reacts with reactivity probe Y to form adduct Z, wherein n ranges from 1 to about 10 and m is at least 1 and m≦n. The fourth step includes optionally dereplicating the product collection of at least one known labeled metabolite to provide a depleted product collection including at least one unknown labeled metabolite. The fifth step includes determining the structure of the at least one unknown labeled metabolite, thereby identifying the natural product comprising NP—[X] n .