(S)-(3-propiolamido-2-sulfopropanoyl)glycine | 1379514-83-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-(3-propiolamido-2-sulfopropanoyl)glycine
• CAS: 1379514-83-6
• 化学式: C₈H₁₀N₂O₇S
• 分子量: 278.243
• InChiKey: FQUNOFUMTGPMAT-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.81
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  149.87
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-(3-propiolamido-2-sulfopropanoyl)glycine 、 N-(2-azidoethyl)-4-[[2,5-dimethoxy-4-[(4-nitrophenyl)diazenyl]phenyl]diazenyl]-N-methylaniline 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以61%的产率得到C₃₁H₃₃N₁₁O₁₁S
  参考文献：
  名称：

  Straightforward synthesis of bioconjugatable azo dyes. Part 2: Black Hole Quencher-2 (BHQ-2) and BlackBerry Quencher 650 (BBQ-650) scaffolds

  摘要：

  A further extension of the efficient synthetic methodology described in Part I, to the aromatic bis-diazo scaffold of Black Hole Quencher-2 dye is presented. Bioconjugatable derivatives bearing either azido, terminal alkyne, or maleimide reactive group were easily obtained as well as the free-phenol form of BlackBerry (R) Quencher 650 (BBQ-650 (R)) initially developed by Berry & Associates, Inc. Company. The efficient conjugation ability of azido- and maleimide-quenchers was demonstrated through the facile preparation of the first water-soluble and formylated BHQ-2 dyes and a FRET-based probe suitable for the in vitro/in cellulo detection of a cancer-associated protease namely urokinase-type plasminogen activator. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.10.054
• 作为产物：
  描述：

  Fmoc-甘氨酸 、 3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-sulfopropanoic acid 、 丙炔酸 在 4-二甲氨基吡啶 、 Wang resin 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 以45%的产率得到(S)-(3-propiolamido-2-sulfopropanoyl)glycine
  参考文献：
  名称：

  New insights into the water-solubilisation of fluorophores by post-synthetic “click” and Sonogashira reactions

  摘要：

  本文介绍了将疏水性荧光染料高效化学转化为可生物接合的水溶性衍生物的新合成方法。这些新型磺化后合成方法的基石是结合使用一种原始的磺化末端炔烃和一种金属介导的反应，即铜催化的惠斯根 1,3-二极环加成反应（"click "反应）或 Sonogashira 交叉偶联反应。

  DOI：

  10.1039/c2ob25428j

文献信息

• Bioconjugatable Azo-Based Dark-Quencher Dyes: Synthesis and Application to Protease-Activatable Far-Red Fluorescent Probes
  作者：Arnaud Chevalier、Cédrik Massif、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1002/chem.201203427

  日期：2013.1.28

  We describe the efficient synthesis and one‐step derivatization of novel, nonfluorescent azo dyes based on the Black Hole Quencher‐3 (BHQ‐3) scaffold. These dyes were equipped with various reactive and/or bioconjugatable groups (azido, α‐iodoacetyl, ketone, terminal alkyne, vicinal diol). The azido derivative was found to be highly reactive in the context of copper‐catalyzed azide–alkyne cycloaddition

  我们描述了基于黑洞Quencher-3（BHQ-3）支架的新型非荧光偶氮染料的高效合成和一步衍生。这些染料配备了各种反应性和/或生物结合性基团（叠氮基，α-碘乙酰基，酮，末端炔烃，邻二醇）。发现叠氮衍生物在铜催化的叠氮化物-炔烃环加成（CuAAC）反应中具有很高的反应活性，可以轻松合成第一批水溶性（磺化衍生物）和醛改性的BHQ-3染料，直接常规偶氮偶联反应无法制备。通过形成稳定的肟或硫醚键，可以轻松地将含醛和α-碘乙酰基的荧光猝灭剂与含氨氧基和半胱氨酸的肽偶联。
• Straightforward synthesis of bioconjugatable azo dyes. Part 1: Black Hole Quencher-1 (BHQ-1) scaffold
  作者：Arnaud Chevalier、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1016/j.tetlet.2014.10.053

  日期：2014.12

  Azo dyes are currently used to quench the fluorescence of energy donors in bioassays through Forster resonance energy transfer (FRET) phenomenon. Common examples of such dark quenchers are DABCYL and the three members of Black Hole Quencher (R) (BHQ) family. Yet, only carboxylic acid and phosphoramidite derivatives of such azo dyes are presently commercially available. This Letter presents a straightforward synthesis method to novel bioconjugatable quenchers derived from BHQ-1 scaffold and equipped with a reactive group being either azido, terminal alkyne, or maleimide. The potential utility of the 'clickable' azido and thiol-reactive derivatives was notably demonstrated through the preparation of the first water-soluble BHQ-1 dye and a FRET-based probe suitable for the detection of urokinase-type plasminogen activator (uPA), a key protease in cancer invasion and metastasis, respectively. (C) 2014 Elsevier Ltd. All rights reserved.