6-[1,3]dioxolan-2-yl-4-oxo-hexanoic acid 9H-fluoren-9-ylmethyl ester | 1040404-87-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 6-[1,3]dioxolan-2-yl-4-oxo-hexanoic acid 9H-fluoren-9-ylmethyl ester
• 英文别名: 9H-fluoren-9-ylmethyl 6-(1,3-dioxolan-2-yl)-4-oxohexanoate
• CAS: 1040404-87-2
• 化学式: C₂₃H₂₄O₅
• 分子量: 380.441
• InChiKey: YKJICTZQMBYUSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-[1,3]dioxolan-2-yl-4-oxo-hexanoic acid 9H-fluoren-9-ylmethyl ester 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 5.0h， 以88%的产率得到4,7-dioxo-heptanoic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Synthesis and structural characterization of carboxyethylpyrrole-modified proteins: mediators of age-related macular degeneration

  摘要：

  Protein modifications in which the e-amino group of lysyl residues is incorporated into a 2-(omega-carboxy-ethyl)pyrrole (CEP) are mediators of age-related macular degeneration (AMD). They promote both angiogenesis into the retina ('wet AMD') and geographic retinal atrophy ('dry AMD'). Blood levels of CEPs are biomarkers for clinical prognosis of the disease. To enable mechanistic studies of their role in promoting AMD, for example, through the activation of B- and T-cells, interaction with receptors, or binding with complement proteins, we developed an efficient synthesis of CEP derivatives, that is especially effective for proteins. The structures of tryptic peptides derived from CEP-modified proteins were also determined. A key finding is that 4,7-dioxoheptanoic acid 9-fluorenylmethyl ester reacts with primary amines to provide 9-fluorenylmethyl esters of CEP-modified proteins that can be deprotected in situ with 1,8-diazabicyclo[5.4.0]undec-7-ene without causing protein denaturation. The introduction of multiple CEP-modifications with a wide variety of CEP: protein ratios is readily achieved using this strategy. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.009
• 作为产物：
  描述：

  9-芴甲醇 、 6-[1,3]dioxolan-2-yl-4-oxo-hexanoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以95%的产率得到6-[1,3]dioxolan-2-yl-4-oxo-hexanoic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Synthesis and structural characterization of carboxyethylpyrrole-modified proteins: mediators of age-related macular degeneration

  摘要：

  Protein modifications in which the e-amino group of lysyl residues is incorporated into a 2-(omega-carboxy-ethyl)pyrrole (CEP) are mediators of age-related macular degeneration (AMD). They promote both angiogenesis into the retina ('wet AMD') and geographic retinal atrophy ('dry AMD'). Blood levels of CEPs are biomarkers for clinical prognosis of the disease. To enable mechanistic studies of their role in promoting AMD, for example, through the activation of B- and T-cells, interaction with receptors, or binding with complement proteins, we developed an efficient synthesis of CEP derivatives, that is especially effective for proteins. The structures of tryptic peptides derived from CEP-modified proteins were also determined. A key finding is that 4,7-dioxoheptanoic acid 9-fluorenylmethyl ester reacts with primary amines to provide 9-fluorenylmethyl esters of CEP-modified proteins that can be deprotected in situ with 1,8-diazabicyclo[5.4.0]undec-7-ene without causing protein denaturation. The introduction of multiple CEP-modifications with a wide variety of CEP: protein ratios is readily achieved using this strategy. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.009

文献信息

• DETECTION OF CARBOXYALKYLPYRROLE OR PENTYLPYRROLE ETHANOLAMINE PHOSPHOLIPIDS
  申请人：CASE WESTERN RESERVE UNIVERSITY

  公开号：US20170176470A1

  公开（公告）日：2017-06-22

  A method of detecting carboxyalkylpyrrole ethanolamine phospholipids (CAP-EPs) or pentylpyrrole ethanolamine phospholipids (CAP-EPs) in a bodily sample from a subject includes obtaining a bodily sample from a subject suspected of including carboxyalkylpyrrole ethanolamine phospholipids (CAP-EPs) or pentylpyrrole ethanolamine phospholipids (PP-EPs) extracting carboxyalkylpyrrole ethanolamine phospholipids or pentylpyrrole ethanolamine phospholipids from the bodily sample; hydrolyzing carboxyalkylpyrrole or pentylpyrrole ethanolamine phospholipids from the extracted with a phospholipase D to form carboxyalkylpyrrole ethanolamine (CAP-ETN) and pentylpyrrole ethanolamine (PP-ETN) derivatives; and determining the amount of carboxyalkylpyrrole ethanolamine (CAP-ETN) and pentylpyrrole ethanolamine (PP-ETN) by mass spectrometry.
• [EN] CARBOXYETHYLPYRROLE COMPOUNDS AND METHODS OF THEIR PRODUCTION<br/>[FR] COMPOSÉS CARBOXYÉTHYLPYRROLE ET PROCÉDÉS POUR LEUR PRODUCTION
  申请人：CLEVELAND CLINIC FOUNDATION

  公开号：WO2008089487A2

  公开（公告）日：2008-07-24

  [EN] The present invention involves methods of anchoring carboxyethylpyrrole (CEP) haptens to carriers via various linkers. Provided herein are 9-fluorenylmethyl (Fm) masked-CEP-linker acids and Fm masked-CEP-linker esters that are useful for the preparation of CEP-linker- carrier derivatives. Also provided are methods of preparing said Fm masked-CEP-linker acids, Fm masked-CEP-linker esters and CEP-linker-carrier derivatives.
  [FR] La présente invention concerne des procédés d'ancrage d'haptènes de carboxyéthylpyrrole (CEP) à des vecteurs via différents lieurs. L'invention concerne des 9-fluorénylméthyle (Fm) masqué-CEP-acides lieurs et des Fm masqué-CEP-esters lieurs qui sont utiles pour la préparation de dérivés CEP-lieur-vecteur. L'invention concerne également des procédés de préparation desdits Fm masqué-CEP-acides lieurs, desdits Fm masqué-CEP-esters lieurs et desdits dérivés CEP-lieur-vecteur.