3-(1-{4-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-butyl}-1H-pyrrol-2-yl)-propionic acid | 1040404-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: 3-(1-{4-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-butyl}-1H-pyrrol-2-yl)-propionic acid
• CAS: 1040404-95-2
• 化学式: C₂₁H₃₂N₄O₄S
• 分子量: 436.575
• InChiKey: QFFHNMJMLVZYIL-ZWOKBUDYSA-N

物化性质

• 沸点：
  787.3±60.0 °C(predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  30.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  112.46
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3-(1-{4-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-butyl}-1H-pyrrol-2-yl)-propionic acid 9H-fluoren-9-yl-methyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到3-(1-{4-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-butyl}-1H-pyrrol-2-yl)-propionic acid
  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