5-羧基四甲基罗丹明 | 150322-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 5-羧基四甲基罗丹明
• 英文名称: 5-carboxytetramethylrhodamine
• 英文别名: 3',6'-bis(dimethylamino)-3-oxo-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid；3',6'-bis(dimethylamino)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid；5-TAMRA；TAMRA；3',6'-Bis(dimethylamino)-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid
• CAS: 150322-05-7
• 化学式: C₂₅H₂₂N₂O₅
• 分子量: 430.46
• InChiKey: DCVXPZDNLDPUES-UHFFFAOYSA-N

物化性质

• 沸点：
  694.4±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.3
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 安全说明：
  S22,S24/25

反应信息

• 作为反应物：
  描述：

  5-羧基四甲基罗丹明 在 N-甲基吗啉 、 四氮唑 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.25h， 生成 Phosphoric acid 1-[4-(3,6-bis-dimethylamino-9-hydroxy-9H-xanthen-9-yl)-3-tert-butylcarbamoyl-benzoyl]-piperidin-4-yl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  A Tetramethyl Rhodamine (Tamra) Phosphoramidite Facilitates Solid-Phase-Supported Synthesis of 5‘-Tamra DNA

  摘要：

  6-Carboxy Tamra 1 was conjugated to:4-hydroxypiperidine with BOP and N-methylmorpholine, and the resulting 5-(N-pipyridyl-4-hydroxy)-Tamra carboxamide 2 was treated with 2-cyanoethyl tetraisopropylphosphorodiamidite to give 5- [N-pipyridyl-4-O-(2-cyanoethyl diisopropylphosphoramidite)]-Tamra carboxamide 3. Solutions of 3 were coupled onto the 5'-hydroxyl of solid-phase-supported DNA fragments with standard amidite coupling techniques. Cleavage and deprotection with aqueous tert-butylamine cocktail gave 5-Tamra-functionalized DNA as well as an additional compound without the Tamra chromophore. A mass spectrum of this product showed the incorporation of tert-butylamine.: The extra product was completely suppressed by including a 5 min acetylation step after coupling. A model study of 3 coupled onto thymidine-functionalized CPG showed similar results. NMR and mass spectra of cleaved products confirmed;the addition of tert-butylamine to the minor product. Coupling a Tamra active ester onto T CPG; which was previously coupled with N-(4-methoxytrityl)piperidyl-4-O-(2-cyanoethyl diisopropylphosphoramidite) A produced. the same major Tamra-bearing product, which coeluted on reverse phase HPLC with the major product generated with 3.

  DOI：

  10.1021/jo0011134
• 作为产物：
  描述：

  3-羟基-N,N-二甲基苯胺 、 偏苯三酸酐 以 甲苯 为溶剂， 反应 12.0h， 以36%的产率得到5-羧基四甲基罗丹明
  参考文献：
  名称：

  Cell-permeable small molecule probes for site-specific labeling of proteinsElectronic supplementary information (ESI) available: experimental details and characterization of compounds. See http://www.rsc.org/suppdata/cc/b3/b309196a/

  摘要：

  我们已经成功合成了一些用于在活细胞中表达的含N端半胱氨酸蛋白质进行位点特异性标记的小分子探针。它们在纯化蛋白质的体外实验中，以及在活细菌细胞的体内实验中，都成功展示了其进行蛋白质位点特异性共价修饰的效用。

  DOI：

  10.1039/b309196a

文献信息

• SOLID SUPPORTS AND PHOSPHORAMIDITE BUILDING BLOCKS FOR OLIGONUCLEOTIDE CONJUGATES
  申请人：AM Chemicals LLC

  公开号：US20180016232A1

  公开（公告）日：2018-01-18

  Novel non-nucleoside solid supports and phosphoramidite building blocks for preparation of synthetic oligonucleotides containing at least one non-nucleosidic moiety conjugated to a ligand of practical interest and synthetic processes for making the same are disclosed. Furthermore, oligomeric compounds are prepared using said solid supports and phosphoramidite building blocks, preferably followed by removal of protecting groups to provide oligonucleotides conjugated to ligands of interest.

  揭示了用于制备含有至少一个非核苷酸基团与实用兴趣配体共轭的合成寡核苷酸的新型非核苷酸固相支持体和磷酰胺酸酯构建块，以及制备这些固相支持体和磷酰胺酸酯构建块的合成过程。此外，使用所述固相支持体和磷酰胺酸酯构建块制备寡聚合物化合物，最好是在去除保护基的情况下，以提供与感兴趣的配体共轭的寡核苷酸。
• Steric-Free Bioorthogonal Labeling of Acetylation Substrates Based on a Fluorine–Thiol Displacement Reaction
  作者：Zhigang Lyu、Yue Zhao、Zakey Yusuf Buuh、Nicole Gorman、Aaron R. Goldman、Md Shafiqul Islam、Hsin-Yao Tang、Rongsheng E. Wang

  DOI：10.1021/jacs.0c05605

  日期：2021.1.27

  We have developed a novel bioorthogonal reaction that can selectively displace fluorine substitutions alpha to amide bonds. This fluorine-thiol displacement reaction (FTDR) allows for fluorinated cofactors or precursors to be utilized as chemical reporters, hijacking acetyltransferase-mediated acetylation both in vitro and in live cells, which cannot be achieved with azide- or alkyne-based chemical

  我们开发了一种新型生物正交反应，可以选择性地将氟取代 α 键到酰胺键。这种氟-硫醇置换反应 （FTDR） 允许将氟化辅因子或前体用作化学报告基因，在体外和活细胞中劫持乙酰转移酶介导的乙酰化，这是基于叠氮化物或炔烃的化学报告基因无法实现的。使用 FTDR 可以将氟乙酰胺标记物进一步转换为生物素或荧光团标签，从而能够对乙酰基底物进行一般检测和成像。这种策略可能会导致底物蛋白的无空间标记平台，扩展我们的化学工具箱，以系统的方式对翻译后修饰进行功能注释。
• [EN] (4-HYDROXYPYRROLIDIN-2-YL)-HYDROXAMATE COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS DE (4-HYDROXYPYRROLIDIN-2-YL)-HYDROXAMATE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：GENENTECH INC

  公开号：WO2019084030A1

  公开（公告）日：2019-05-02

  The present disclosure relates to bifunctional compounds, which can be used as modulators of targeted ubiquitination. In particular, the present disclosure is directed to compounds which contain on one end a VHL ligand moiety, which binds to the VHL E3 ubiquitin ligase, and on the other end a moiety that binds a target protein such that degradation of the target protein/polypeptide is effectuated. Also disclosed are VHL ligands.

  本公开涉及双功能化合物，可用作靶向泛素化的调节剂。具体而言，本公开涉及包含一端为VHL配体基团的化合物，该基团结合VHL E3泛素连接酶，另一端含有结合靶蛋白的基团，从而实现对靶蛋白/多肽的降解。还公开了VHL配体。
• [EN] (4-HYDROXYPYRROLIDIN-2-YL)-HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS (4-HYDROXYPYRROLIDIN-2-YL)-HÉTÉROCYCLIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：GENENTECH INC

  公开号：WO2019084026A1

  公开（公告）日：2019-05-02

  The present disclosure relates to bifunctional compounds of formula (I), which can be used as modulators of targeted ubiquitination. In particular, the present disclosure is directed to compounds which contain on one end a VHL ligand moiety, which binds to the VHL E3 ubiquitin ligase, and on the other end a moiety that binds a target protein such that degradation of the target protein/polypeptide is effectuated. Also disclosed are VHL ligands of formula (III).

  本公开涉及公式（I）的双功能化合物，可用作靶向泛素化的调节剂。具体而言，本公开涉及包含一端为VHL配体基团的化合物，该基团结合到VHL E3泛素连接酶，另一端为结合靶蛋白的基团，从而实现靶蛋白/多肽的降解。还公开了公式（III）的VHL配体。
• Metal-Dependent DNA Recognition and Cell Internalization of Designed, Basic Peptides
  作者：Soraya Learte-Aymamí、Natalia Curado、Jéssica Rodríguez、M. Eugenio Vázquez、José L. Mascareñas

  DOI：10.1021/jacs.7b07422

  日期：2017.11.15

  while the peptide brHis2 fails to translocate across cell membranes on its own, addition of the palladium reagent induces an efficient cell internalization of this peptide. In short, we report (1) a designed, short peptide that displays highly selective, major groove DNA binding, (2) a reversible, metal-dependent DNA interaction, and (3) a metal-promoted cell internalization of this basic peptide.

  GCN4 bZIP转录因子的DNA碱性区域（br）的一个片段已被修饰，在其N端的第i和i +4位置包括两个His残基。所得的单体肽（brHis 2）不结合其共有靶DNA位点（5'-GTCAT-3'）。但是，添加Pd（en）Cl 2（en，乙二胺）可以促进高亲和力相互作用，并具有对该序列的出色选择性。通过加入少量过量的钯螯合剂可以分解肽-DNA络合物，并且可以通过控制量的金属络合物或螯合剂的作用可逆地多次切换相互作用。重要的是，而肽brHis 2钯试剂自身不能跨细胞膜移位，所以添加钯试剂可诱导该肽有效地细胞内在化。简而言之，我们报道了（1）设计的短肽，该肽显示出高度选择性的大沟DNA结合，（2）可逆的，金属依赖性的DNA相互作用，以及（3）这种碱性肽的金属促进的细胞内在化。