6-羧基荧光素二硬脂酸酯N-羟基琥珀酰亚胺酯 | 197850-75-2

• 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: 6-羧基荧光素二硬脂酸酯N-羟基琥珀酰亚胺酯
• 英文名称: 1-{[(3,6-di-O-pivaloyl)fluorescein-6-yl]oxy}pyrrolidine-2,5-dione
• 英文别名: 6-carboxyfluorescein-3',6'-dipivalat NHS-ester；5,6-Carboxyfluorescein dipivalate succinimide ester；(2,5-dioxopyrrolidin-1-yl) 3',6'-bis(2,2-dimethylpropanoyloxy)-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-carboxylate
• CAS: 197850-75-2
• 化学式: C₃₅H₃₁NO₁₁
• 分子量: 641.631
• InChiKey: WEULGCXFMIDYQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  778.6±70.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  47
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-羧基荧光素二硬脂酸酯N-羟基琥珀酰亚胺酯 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 反应 3.5h， 以1.25 g的产率得到3',6'-di(trimethylacetyloxy)-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carbonyl azide
  参考文献：
  名称：

  A fluorescein-containing, small-molecule, water-soluble receptor for cytosine free bases

  摘要：

  In this study, we synthesized small-molecule, water-soluble, fluorescein-containing ureido compounds 6 and 8 as target receptors for cytosine free bases and then investigated the binding of cytosine free bases with the receptors using (15)N NMR spectroscopy and partially labeled cytosine-2,4-(13)C-1,3,4-(15)N-cytosine. Binding with the receptor 6a (the disodium form of 6) caused the chemical shift of the nitrogen atom of the amino group of cytosine to move downfield; binding of the receptor 8a (the disodium form of 8), which is possessing no corresponding aryl nitrogen atom, had no effect on this signal. Fluorescence spectroscopy revealed that binding of cytosine and its derivatives led to quenching of the fluorescence of receptor 6a; in contrast, the quenching of receptor 8a was only slightly affected by cytosine. Because the fluorescence of 6a was not quenched by either deoxycytidine or uracil, it appears that this receptor is a specific for cytosine among the DNA bases. We used the fluorescence of 6a to measure the apparent binding constants for various cytosine derivatives, including the anticancer prodrug 5-fluorocytosine. Receptor 6a is the first small-molecule, water-soluble fluorescent receptor for the specific binding of cytosine free bases in aqueous solution. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.013
• 作为产物：
  描述：

  6-羧基荧光素 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 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 72.0h， 生成 6-羧基荧光素二硬脂酸酯N-羟基琥珀酰亚胺酯
  参考文献：
  名称：

  Synthesis of 5- and 6-Hydroxymethylfluorescein Phosphoramidites

  摘要：

  DOI：

  10.1021/jo991449h

文献信息

• Linker-Free Fluorophore-Labeled Oligonucleotides: Synthesis of 3′-Fluoresceinylthymidine Building Blocks and their Coupling Reactions
  作者：Clemens Richert、Niels Griesang、Eric Kervio

  DOI：10.1055/s-2005-870024

  日期：——

  Reported here are the syntheses of two thymidine derivatives with an amide-linked 6-carboxyfluorescein residue at their 3′-position that are suitable for the synthesis of fluorophore-labeled oligonucleotides. The first is a 5′-phosphoramidite with a pivaloyl-protected carboxyfluorescein residue in the lactone form. It was prepared from 3′-azido-3′-deoxythymidine (AZT) in three steps and 73% overall yield and coupled on solid support. The second is an imidazolide of thymidine 5′-monophosphate that was obtained from AZT in five steps and 48% overall yield. The imidazolide can be coupled to amino-terminated nucleic acids in aqueous solution.

  这里报道了两种胸苷衍生物的合成，其 3' 位具有酰胺连接的 6-羧基荧光素残基，适合合成荧光团标记的寡核苷酸。第一种是内酯形式的具有新戊酰保护的羧基荧光素残基的 5'-亚磷酰胺。它由 3'-叠氮基-3'-脱氧胸苷 (AZT) 分三步制备而成，总产率为 73%，并偶联在固体支持物上。第二种是胸苷 5'-单磷酸咪唑化物，由 AZT 分五步得到，总产率为 48%。咪唑化物可以在水溶液中与氨基封端的核酸偶联。
• Fluorescent Mimetics of CMP-Neu5Ac Are Highly Potent, Cell-Permeable Polarization Probes of Eukaryotic and Bacterial Sialyltransferases and Inhibit Cellular Sialylation
  作者：Johannes J. Preidl、Vinayaga S. Gnanapragassam、Michael Lisurek、Jörn Saupe、Rüdiger Horstkorte、Jörg Rademann

  DOI：10.1002/anie.201400394

  日期：2014.5.26

  Oligosaccharides of the glycolipids and glycoproteins at the outer membranes of human cells carry terminal neuraminic acids, which are responsible for recognition events and adhesion of cells, bacteria, and virus particles. The synthesis of neuraminic acid containing glycosides is accomplished by intracellular sialyl transferases. Therefore, the chemical manipulation of cellular sialylation could be

  人细胞外膜上的糖脂和糖蛋白的寡糖带有末端神经氨酸，负责识别事件以及细胞，细菌和病毒颗粒的粘附。含有神经氨酸的糖苷的合成是通过细胞内的唾液酸转移酶完成的。因此，细胞唾液酸化的化学操作对于干扰癌症的发展，炎症和感染可能非常重要。本文描述了唾液酸转移酶的第一纳摩尔荧光抑制剂的开发和应用。发现所获得的糖核苷酸模拟物可结合所有四种市售并在荧光偏振测定中测试的真核和细菌唾液酸转移酶。而且，观察到，阴离子模拟物快速有效地侵入囊泡中的细胞，并转移到围绕CHO细胞核的细胞器中。新化合物抑制两种细胞系中的细胞唾液酸化，并为研究细胞唾液酸化开辟了新的前景。
• WO2006/63717
  申请人：——

  公开号：——

  公开（公告）日：——
• ——
  作者：Natalya Ramzaeva、Helmut Rosemeyer、Peter Leonard、Klaus Mühlegger、Frank Bergmann、Herbert von der Eltz、Frank Seela

  DOI：10.1002/1522-2675(20000607)83:6<1108::aid-hlca1108>3.0.co;2-9

  日期：2000.6.7

  The 2'-deoxypseudouridine (5) was functionalized at N(1) with methyl acrylate by Michael addition. The resulting methyl 2'-deoxypseudouridine-1-propanoate (6) was converted to the phosphoramidite 8 and to the amino-functionalized derivative 9, which was transformed into the fluorescein-labeled phosphoramidites 14 and 16. Fluorescent oligonucleotides were synthesized either from these building blocks or by post-synthetic modification of oligomers containing 2'-deoxypseudouridine subunits. The stability of oligonucleotide duplexes was determined from the melting profiles, measured by UV- or VIS-light absorbance, as well as from the fluorescence emission spectra. While small spacer residues did not affect the thermal stability of the 2'-deoxypseudouridine-containing duplexes, large dye residues led to destabilization.
• POLYMERASE-INDEPENDENT ANALYSIS OF THE SEQUENCE OF POLYNUCLEOTIDES
  申请人：Rojas Stütz Jan André

  公开号：US20100029008A1

  公开（公告）日：2010-02-04

  The present invention concerns methods of polymerase independent template directed elongation of polynucleotides, nucleotide building blocks used in these methods as well as the use of the methods and building blocks for the determination of nucleotide sequences, in particular for the determination of SNPs, base modifications, mutations, rearrangements and methylation patterns.