5-[(2',5'-dioxo-1'-pyrrolidinyl)oxy]-5-oxopentanoyl chloride | 117746-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 5-[(2',5'-dioxo-1'-pyrrolidinyl)oxy]-5-oxopentanoyl chloride
• 英文别名: 5-<(2,5-dioxo-1-pyrrolidinyl)oxy>-5-oxopentanoyl chloride；5-[(2,5-dioxo-1-pyrrolidinyl)oxy]-5-oxypentanoyl chlodide；N-hydroxysuccinimidyl hemiglutaryl chloride；succinimido-oxycarbonyl-butyryl chloride；Pentanoyl chloride, 5-[(2,5-dioxo-1-pyrrolidinyl)oxy]-5-oxo-；(2,5-dioxopyrrolidin-1-yl) 5-chloro-5-oxopentanoate
• CAS: 117746-42-6
• 化学式: C₉H₁₀ClNO₅
• 分子量: 247.635
• InChiKey: GFMJEFVIJCQAEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(2',5'-dioxo-1'-pyrrolidinyl)oxy]-5-oxopentanoyl chloride 在 三乙胺 、 二溴三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 戊酰胺,N-[4-(溴甲基)苯基]-5-[(2,5-二羰基-1-吡咯烷基)氧代]-5-羰基-
  参考文献：
  名称：

  Antibody bait and switch catalysis: a survey of antigens capable of inducing abzymes with acyl-transfer properties

  摘要：

  Antibodies have been shown to catalyze acyl-transfer reactions. Various antigens have been applied to these hydrolytic reactions, but typically all encompass the same theme of incorporating a monoanionic phosphonate/phosphonamidate. To expand the scope and capabilities of these abzymes, we have directed our attention toward new strategies in antigen design. One method, which we have termed ''bait and switch'' catalysis, uses haptens to elicit amino acid(s) within the binding pocket of an antibody that can accelerate hydrolysis. We reported initial success of this methodology utilizing the cationic hapten 1 for obtaining abzymes that hydrolyzed benzoate ester 6. In addition, we showed how the structurally identical but neutral hapten 2 was unable to induce catalytic antibodies. To further identify those factors critical in the generation of hydrolytic abzymes via our bait and switch methodology, we have (1) designed and synthesized three new homologues of 1 in which we have varied the type of charge/no charge and its location, (2) screened and identified catalytic antibodies from these antigens, (3) determined affinity constants of a number of these monoclonal antibodies (catalytic and noncatalytic) for their respective haptens and possible substrates (ester/amide), (4) performed steady-state kinetics, inducing a pH-rate profile on one of these abzymes, and (5) used chemical modifying reagents to identify which amino acid residue(s) are involved in these catalytic processes.

  DOI：

  10.1021/ja00014a039
• 作为产物：
  描述：

  5-[(2,5-dioxopyrrolidin-1-yl)oxy]-5-oxopentanoic acid 在 氯化亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-[(2',5'-dioxo-1'-pyrrolidinyl)oxy]-5-oxopentanoyl chloride
  参考文献：
  名称：

  Templated alkylation of hexahistidine with Baylis–Hillman esters

  摘要：

  在Ni2+、Cu2+或Zn2+阳离子存在下，在pH值为中性、浓度为微摩尔的水溶液中，实现了六组苷的一个咪唑环与连接到硝基三乙酸残基的BaylisâHillman酯的烷基化。通过 "click "1,3-二极环加成反应将荧光标签连接到带有炔基的重组蛋白A上，证明了这种方法在选择性地对His标记的重组蛋白进行功能化方面的实用性。

  DOI：

  10.1039/c3cc43271h

文献信息

• Phosphorylation of 1,3-Di(N-alkyl)Azoles by Phosphorus(V) Acid Chlorides — a Route to Potential Haptens Derived from Phosphinic Acids
  作者：Igor V. Komarov、Mikhail Yu. Kornilov、Aleksandr V. Turov、Marian V. Gorichko、Vladimir O. Popov、Andrey A. Tolmachev、Anthony J. Kirby

  DOI：10.1016/0040-4020(95)00797-c

  日期：1995.11

  Phosphorylation of N-alky lated imidazoles and benzimidazoles at C-2 by CH3POCl2, PhPOCl2-POCl3 in pyridine-triethylamine solution is described. The formed heteroaryl-substituted phosphinic or phosphonic acid chlorides were transformed without isolation into the corresponding phosphinic (phosphonic) acids, their salts or amides with moderate yields This reaction opens a simple way to potential haptens derived from

  CH 3 POCl 2，PhPOCl 2 -POCl 3使N-烷基化的咪唑和苯并咪唑在C-2处磷酸化描述了在吡啶-三乙胺溶液中的溶液。形成的杂芳基取代的次膦酸或膦酰氯无需分离即可转化为相应的次膦酸（膦酸），其盐或酰胺，收率适中。该反应为衍生自次膦酸的潜在半抗原开辟了一条简单的途径。许多反应，可用于获得催化抗体。用作半抗原前体的官能化杂芳基取代的次膦酸是通过1-烷基-5-硝基苯并咪唑的磷酸化或使用新的磷酸化试剂-（4-三氯甲基苯基）膦酸二氯丁酮获得的。
• A Light-Activated Antibody Catalyst
  作者：Matthew J. Taylor、Timothy Z. Hoffman、Jari T. Yli-Kauhaluoma、Richard A. Lerner、Kim D. Janda

  DOI：10.1021/ja982711r

  日期：1998.12.1

  per antibody) occurred. The singular product obtained in the antibody-catalyzed reaction was not observed in the uncatalyzed reaction unless the pH was lowered below 4. Studies suggested that the interplay of conformational control and chemical catalysis were responsible for the high specificity. A change in protonation state of the antibody was correlated with the inclusion of a new reaction pathway

  研究了用于多步 Norrish II 型光化学反应的催化抗体。α-酮酰胺底物 1b 吸收光能产生高能双自由基中间体，然后由抗体微环境引导形成四氢吡嗪 13，在 280 nm 照射下 kcat 为 1.4 × 10-3 min-1，对映体过量78%。用放射性标记底物进行的抗体催化反应表明几乎没有发生自我失活（每个抗体四次转换后 6.8 mol% 的共价修饰）。在未催化反应中观察不到在抗体催化反应中获得的单一产物，除非 pH 值低于 4。研究表明，构象控制和化学催化的相互作用是造成高特异性的原因。
• Reagents for lysergic acid diethylamide immunoassay
  申请人：Roche Diagnostics Corporation

  公开号：US06063908A1

  公开（公告）日：2000-05-16

  The present invention provides hapten derivatives that are useful for the preparation of antigens, antibodies and reagents having superior performance characteristics for use in immunoassays for the detection of LSD and nor-LSD. In the present invention the LSD nucleus is derivatized out of the indole nitrogen to form an aminoalkyl derivative. Derivatives have also been synthesized out of the piperidine nitrogen of the LSD nucleus. The resulting haptens can then be further modified at these functionalized positions for linking to appropriate antigenic or labelling groups to provide reagents for LSD immunoassays having excellent sensitivity and selectivity for both LSD and nor-LSD.

  本发明提供了一种可用于制备抗原、抗体和试剂的半抗原衍生物，这些试剂在用于检测LSD和去甲-LSD的免疫分析中具有优良的性能特征。在本发明中，LSD核心通过吲哚氮原子衍生化形成氨基烷基衍生物。还从LSD核心的哌啶氮原子合成了衍生物。然后可以在这些功能化位置进一步修饰得到的半抗原，以便与适当的抗原或标记基团连接，为LSD免疫分析提供具有对LSD和去甲-LSD都具有极佳灵敏性和选择性的试剂。
• Synthesis and biochemical evaluation of cephalosporin analogues equipped with chemical tethers
  作者：Lisa M. Miller、Reyme Herman、Ivan Gyulev、Thomas F. Krauss、Gavin H. Thomas、Anne-Kathrin Duhme-Klair

  DOI：10.1039/d0ra04893c

  日期：——

  bioconjugation with a desired substrate but the effects of these changes are often not evaluated. Here, we set out to determine the effects of attaching functional handles to a first-generation cephalosporin. A series of cephalexin derivatives was prepared, equipped with chemical tethers suitable for the site-selective conjugation of antibiotics to functionalised surfaces. The tethers were positioned

  分子探针通常需要结构修饰以允许与所需底物固定或生物共轭，但这些变化的影响通常不被评估。在这里，我们着手确定将功能手柄连接到第一代头孢菌素的效果。制备了一系列头孢氨苄衍生物，配备有化学系链，适用于抗生素与功能化表面的位点选择性结合。系链远离β-内酰胺环，以确保对抗生素药效团的影响最小。在此，评估了修饰的抗生素与治疗靶点、青霉素结合蛋白结合的活性，并显示其保持结合相互作用。此外，四种β-内酰胺酶（TEM-1，研究了 CTX-M-15、AmpC、NDM-1) 并确定了系链对催化效率的影响。发现 CTX-M-15 有利于在没有系链的情况下水解母体抗生素，而发现 AmpC 和 NDM-1 有利于修饰的类似物。此外，评估衍生物的抗微生物活性以研究结构修饰对母体药物头孢氨苄抗微生物活性的影响。
• Development of Chemical Probes for Functional Analysis of Anticancer Saponin OSW‐1
  作者：Rina Komatsu、Kaori Sakurai

  DOI：10.1002/tcr.201900042

  日期：2019.12

  reviews recent progress in the development of OSW‐1 derived probes for exploring the mechanism of its action. The key to the probe development is a judicious choice of functionalization sites and a selective functionalization strategy. The types of probes include fluorescent probes for cellular imaging analysis and affinity probes for target identification analysis.

  近年来，在天然产物的目标识别研究中，基于化学探针的方法已被证明是有效的。OSW-1是一种天然的皂素类产品，对各种癌细胞具有高度有效的选择性细胞毒性。了解其作用机理对于开发具有潜在新型靶途径的抗癌药物很重要。此帐户回顾了OSW-1衍生探针在探索其作用机理方面的最新进展。探针开发的关键是明智选择功能化位点和选择性功能化策略。探针的类型包括用于细胞成像分析的荧光探针和用于靶标鉴定分析的亲和探针。