己二酸1-(2,5-二氧代-1-吡咯烷基)酯6-甲酯 | 118380-06-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 己二酸1-(2,5-二氧代-1-吡咯烷基)酯6-甲酯
• 英文名称: 1-methyl 6-succinimidyl adipate
• 英文别名: methyl succinimidyl adipate；Methyl N-Succinimidyl Adipate；6-O-(2,5-dioxopyrrolidin-1-yl) 1-O-methyl hexanedioate
• CAS: 118380-06-6
• 化学式: C₁₁H₁₅NO₆
• 分子量: 257.243
• InChiKey: ILDXDBSWYJDHAL-UHFFFAOYSA-N

物化性质

• 熔点：
  53°C
• 沸点：
  356℃
• 密度：
  1.29
• 闪点：
  169℃
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  己二酸1-(2,5-二氧代-1-吡咯烷基)酯6-甲酯 在 过氧化苯甲酰 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成 N-methyl>methyl>-N^α-<1-(6-methyladipyl)>glycinamide
  参考文献：
  名称：

  Synthesis of Cluster Galactosides with High Affinity for the Hepatic Asialoglycoprotein Receptor

  摘要：

  High-affinity Ligands for the asialoglycoprotein receptor, which is uniquely localized on the parenchymal liver cell and recognizes oligoantennary galactosides, might be utilized as homing device to specifically target drugs or genes to parenchymal liver cells. In the present study, the synthesis of galactose-terminated triantennary glycosides, provided with various spacers between the beta-galactopyranosyl moieties and the branching point of the dendrite, is described. N-[Tris[[(methylthio)methoxy]methyl]methyl]-N-alpha-[1-(6-methyladipy)]glycinamide (3b) was glycosylated with monogalactosyl derivatives, containing propanediol or ethylene glycol units as hydrophilic spacer moieties, to yield the corresponding cluster galactosides. To determine the affinity of the cluster galactosides for the asialoglycoprotein receptor, we have performed competition studies of [I-125]ASOR binding, a specific ligand for the asialoglycoprotein receptor, to isolated parenchymal cells. The affinity for the asialoglycoprotein receptor significantly increased with increasing spacer length. N-[[[Tris-O-(beta-D-galactopyranosyl)-3,6,9-trioxaundecanoxy]methoxy]methyl]-N-alpha-[1-(6-methyladipyl)]glycinamide (4e), a cluster galactoside provided with a 20 Angstrom spacer, possessed an at least 2000-fold higher affinity for the receptor than N-[[tris-O-(beta-D-galactopyranosyl)methyl]methyl]-N-alpha -[1-(6-methyladipyl)]glycinamide (4a), a cluster galactoside lacking the spacer. It is concluded that vicinal galactosyl moieties within a cluster galactoside are more optimal recognized by the galactose binding sites of the asialoglycoprotein receptor upon proper spacing. The most potent galactoside, TG(20 Angstrom), may constitute an attractive targeting device for the specific delivery of drugs and/or genes to the parenchymal liver cell.

  DOI：

  10.1021/jm00009a014
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 脂肪酸甲酯 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 己二酸1-(2,5-二氧代-1-吡咯烷基)酯6-甲酯
  参考文献：
  名称：

  1-（2-氯乙基）-3-烷基-3-酰基三氮烯对DNA烷基化的特异性取决于酰基的结构：动力学和产物研究。

  摘要：

  单独研究了小牛胸腺DNA与十个具有不同酰基侧链结构的1-（2-氯乙基）-3-烷基-3-酰基苯甲酰氮的反应，或在pH 7.0磷酸盐缓冲液中在猪肝酯酶存在下的反应。在几种关键的三氮烯中，酰基取代基包含一个游离的羧酸基团。在反应混合物中存在酯酶的情况下，所得的DNA烷基化水平可能与三氮烯分解的动力学速率相关。在这些条件下，主要的分解途径涉及母体三氮烯的脱酰作用并最终产生链烷重氮离子。该中间体随后将DNA-鸟嘌呤烷基化，得到7-烷基鸟嘌呤作为主要反应产物。在没有酯酶的情况下，DNA烷基化的顺序对所有的acyltriazenes都不与它们各自的分解速率相关，从而得出结论，三氮烯不会被未催化的N（2）-N（3）杂多裂解的预期模式分解。N（3）-甲基三氮烯的主要DNA烷基化产物是7-甲基鸟嘌呤，而不是预期的7-（氯乙基）-和7-（羟乙基）鸟嘌呤，这表明酰基正在被水解。但是，与预测相反，在该位置具有N（3

  DOI：

  10.1021/tx950155y

文献信息

• Antibodies which catalyze hydrolysis of ester bonds
  申请人：Scripps Clinic and Research Foundation

  公开号：US05030717A1

  公开（公告）日：1991-07-09

  An analog-ligand having a conformation that substantially corresponds to the conformation of a hydrolytic transition state of an amide or ester reactant ligand is used to produce receptor molecules of predetermined specificity. The receptor molecules include an antibody combining site that binds to a reactant ligand and thereby stabilizes the tetrahedral carbon atom of the amide or ester hydrolysis transition state of that reactant ligand to catalytically hydrolyze the reactant ligand at a predetermined site.

  具有与酰胺或酯反应物配体的水解过渡态构象基本对应的模拟配体用于产生具有预定特异性的受体分子。这些受体分子包括一个与反应物配体结合的抗体结合位点，从而稳定酰胺或酯水解过渡态的四面体碳原子，以在预定位置催化水解反应物配体。
• Antibody combining sites that exhibit amide or ester synthase activity
  申请人：Scripps Clinic and Research Foundation

  公开号：US04900674A1

  公开（公告）日：1990-02-13

  A phosphorous-containing analog-ligand having a conformation that substantially corresponds to the conformation of an amide- or ester-forming transition state is used to induce production of receptor molecules whose antibody combining sites have amide or ester synthase catalytic activity when reacted with a ligand containing (i) a carbonyl carbon atom and (ii) an amine or alcohol group that are structurally capable of forming a preselected carboxylic amide or ester bond.

  含磷的类似配体，其构象基本对应于酰胺或酯形成过渡态的构象，用于诱导产生具有酰胺或酯合成酶催化活性的受体分子，当与含有（i）羰基碳原子和（ii）结构上能够形成预选羧酰胺或酯键的胺基或羟基的配体反应时。
• Antibody combining sites that exhibit stereoselective synthase activity,
  申请人：Scripps Clinic and Research Foundation

  公开号：US05079152A1

  公开（公告）日：1992-01-07

  A phosphorus-containing analog-ligand having a stereoconfiguration that substantially corresponds to the stereoconfiguration of an amide- or ester-forming transition state is used to induce production of receptor molecules whose antibody combining sites have stereospecific amide or ester synthase catalytic activity when reacted with a ligand containing (i) a carbonyl carbon atom and (ii) an amine or alcohol group that are structurally capable of forming a preselected stereoisomer of a carboxylic amide or ester.

  使用含磷的类似配体，其立体构型与酰胺或酯形成的过渡态的立体构型基本对应，用于诱导产生受体分子，其抗体结合位点具有立体特异性酰胺或酯合成酶催化活性，当与含有（i）羰基碳原子和（ii）结构上能够形成预选立体异构体的羧酸酰胺或酯的胺或醇基团的配体反应时。
• Fluorescent dyes, energy transfer couples and methods
  申请人：——

  公开号：US20040073014A1

  公开（公告）日：2004-04-15

  Fluorescent dyes, fluorescence energy transfer dye couples, multi-color dye sets, can be employed in art-recognized assays and certain novel methods, such as in proximity assays.

  荧光染料、荧光能量转移染料偶联物、多色染料组合，可用于艺术识别测定和某些新颖方法，如邻近测定。
• Specificity of DNA Alkylation by 1-(2-Chloroethyl)-3-alkyl-3-acyltriazenes Depends on the Structure of the Acyl Group:  Kinetic and Product Studies
  作者：Marilyn B. Kroeger Smith、Brigitte F. Schmidt、Grzegorz Czerwinski、Lisa A. Taneyhill、Emily J. Snyder、Adam M. Kline、Christopher J. Michejda、Richard H. Smith

  DOI：10.1021/tx950155y

  日期：1996.1.1

  principal reaction product. In the absence of esterase, the order of DNA alkylation for all of the acyltriazenes did not correlate with their respective rates of decomposition, leading to the conclusion that the triazenes did not decompose by the expected mode of uncatalyzed N(2)-N(3) heterolyic cleavage. The major DNA alkylation product from the N(3)-methyltriazenes was 7-methylguanine, instead of the expected

  单独研究了小牛胸腺DNA与十个具有不同酰基侧链结构的1-（2-氯乙基）-3-烷基-3-酰基苯甲酰氮的反应，或在pH 7.0磷酸盐缓冲液中在猪肝酯酶存在下的反应。在几种关键的三氮烯中，酰基取代基包含一个游离的羧酸基团。在反应混合物中存在酯酶的情况下，所得的DNA烷基化水平可能与三氮烯分解的动力学速率相关。在这些条件下，主要的分解途径涉及母体三氮烯的脱酰作用并最终产生链烷重氮离子。该中间体随后将DNA-鸟嘌呤烷基化，得到7-烷基鸟嘌呤作为主要反应产物。在没有酯酶的情况下，DNA烷基化的顺序对所有的acyltriazenes都不与它们各自的分解速率相关，从而得出结论，三氮烯不会被未催化的N（2）-N（3）杂多裂解的预期模式分解。N（3）-甲基三氮烯的主要DNA烷基化产物是7-甲基鸟嘌呤，而不是预期的7-（氯乙基）-和7-（羟乙基）鸟嘌呤，这表明酰基正在被水解。但是，与预测相反，在该位置具有N（3