malonic acid N-hydroxylsuccinimidyl half ester

• 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: malonic acid N-hydroxylsuccinimidyl half ester
• 英文别名: N-hydroxysuccinimidyl malonate；3-((2,5-Dioxopyrrolidin-1-yl)oxy)-3-oxopropanoic acid；3-(2,5-dioxopyrrolidin-1-yl)oxy-3-oxopropanoic acid
• 化学式: C₇H₇NO₆
• 分子量: 201.136
• InChiKey: SKCBDTKJZDYLQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  辅酶 A 、 malonic acid N-hydroxylsuccinimidyl half ester 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 12.17h， 以93.8%的产率得到丙二酰辅酶A-钠盐
  参考文献：
  名称：

  Rapid preparation of (methyl)malonyl coenzyme A and enzymatic formation of unusual polyketides by type III polyketide synthase from Aquilaria sinensis

  摘要：

  (Methyl) malonyl coenzyme A was rapidly and effectively synthesized by a two-step procedure involving preparation of N-hydroxysuccinimidyl (methyl) malonate from (methyl) Meldrum's acid, and followed by transesterification with coenzyme A. The synthesized (methyl) malonyl coenzyme A could be well accepted and assembled to 4-hydroxy phenylpropionyl coenzyme A by type III polyketide synthase from Aquilaria sinensis to produce dihydrochalcone and 4-hydroxy-3,5-dimethyl-6-(4-hydroxyphenethyl)-2H-pyrone as well as 4-hydroxy-3,5-dimethyl-6-(5-(4-hydroxyphenyl)-3-oxopentan-2-yl)-2H-pyrone. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.01.045
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 丙二酸环(亚)异丙酯 以 甲苯 为溶剂， 以54%的产率得到malonic acid N-hydroxylsuccinimidyl half ester
  参考文献：
  名称：

  活化丙二酸半酯的自缩合：聚酮化合物生物合成中脱羧性克莱森缩合的模型

  摘要：

  丙二酸半含氧酸酯与N-羟基琥珀酰亚胺基酯形成试剂的反应导致自缩合，从而提供相应的1，3-丙酮二羧酸二酯。此新方法不需要二价金属螯合剂或配位溶剂即可成功缩合。

  DOI：

  10.1016/j.tetlet.2003.08.014

文献信息

• Self-condensation of activated malonic acid half esters: a model for the decarboxylative Claisen condensation in polyketide biosynthesis
  作者：Youngha Ryu、A.Ian Scott

  DOI：10.1016/j.tetlet.2003.08.014

  日期：2003.9

  The reaction of a malonic acid half oxyester with a N-hydroxysuccinimidyl ester-forming reagent resulted in self-condensation to provide the corresponding 1,3-acetonedicarboxylic acid diester. This new method does not require a divalent metal chelator or a coordinating solvent for successful condensation.

  丙二酸半含氧酸酯与N-羟基琥珀酰亚胺基酯形成试剂的反应导致自缩合，从而提供相应的1，3-丙酮二羧酸二酯。此新方法不需要二价金属螯合剂或配位溶剂即可成功缩合。
• SILOXANE LIGANDS TO BE USED FOR DISPERSING QUANTUM DOTS IN SILICONE HOSTS TO OBTAIN COLOR CONVERTERS FOR LED LIGHTING
  申请人：KONINKLIJKE PHILIPS N.V.

  公开号：US20170222097A1

  公开（公告）日：2017-08-03

  The invention provides a luminescent material comprising wavelength converter nanoparticles ( 120 ) with siloxane polymer capping ligands ( 130 ) associated to the wavelength converter nanoparticles ( 120 ), wherein the siloxane polymer capping ligands ( 130 ) comprise siloxane polymers which comprise at least one capping group comprising a terminal carboxylic acid group, wherein the capping group comprises in total at least six carbon atoms.
• Rapid preparation of (methyl)malonyl coenzyme A and enzymatic formation of unusual polyketides by type III polyketide synthase from Aquilaria sinensis
  作者：Bo-Wen Gao、Xiao-Hui Wang、Xiao Liu、She-Po Shi、Peng-Fei Tu

  DOI：10.1016/j.bmcl.2015.01.045

  日期：2015.3

  (Methyl) malonyl coenzyme A was rapidly and effectively synthesized by a two-step procedure involving preparation of N-hydroxysuccinimidyl (methyl) malonate from (methyl) Meldrum's acid, and followed by transesterification with coenzyme A. The synthesized (methyl) malonyl coenzyme A could be well accepted and assembled to 4-hydroxy phenylpropionyl coenzyme A by type III polyketide synthase from Aquilaria sinensis to produce dihydrochalcone and 4-hydroxy-3,5-dimethyl-6-(4-hydroxyphenethyl)-2H-pyrone as well as 4-hydroxy-3,5-dimethyl-6-(5-(4-hydroxyphenyl)-3-oxopentan-2-yl)-2H-pyrone. (C) 2015 Elsevier Ltd. All rights reserved.