ethyl N-(2-Boc-aminoethyl)-N-(5-iodouracil-1-yl) glycinate | 431042-63-6

• 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: ethyl N-(2-Boc-aminoethyl)-N-(5-iodouracil-1-yl) glycinate
• 英文别名: ethyl 2-[[2-(5-iodo-2,4-dioxopyrimidin-1-yl)acetyl]-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]acetate
• CAS: 431042-63-6
• 化学式: C₁₇H₂₅IN₄O₇
• 分子量: 524.313
• InChiKey: OFQVGEYIGHBUQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.06
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  139.8
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl N-(2-Boc-aminoethyl)-N-(5-iodouracil-1-yl) glycinate 在 bis-triphenylphosphine-palladium(II) chloride 、 三氟乙酸 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  响应性荧光PNA类似物作为检测癌基因G-四链体基序和有毒核糖体失活蛋白活性的工具

  摘要：

  柔和的光芒：响应灵敏且干扰最小的荧光PNA类似物探针可有效检测人类癌基因启动子区域的G四联体基序和核糖体失活蛋白毒素的去嘌呤活性。

  DOI：

  10.1002/cbic.201600192
• 作为产物：
  描述：

  5-碘尿嘧啶 、 ethyl N-(Boc-aminoethyl)-N-(chloroacetyl)glycinate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以49%的产率得到ethyl N-(2-Boc-aminoethyl)-N-(5-iodouracil-1-yl) glycinate
  参考文献：
  名称：

  响应性荧光PNA类似物作为检测癌基因G-四链体基序和有毒核糖体失活蛋白活性的工具

  摘要：

  柔和的光芒：响应灵敏且干扰最小的荧光PNA类似物探针可有效检测人类癌基因启动子区域的G四联体基序和核糖体失活蛋白毒素的去嘌呤活性。

  DOI：

  10.1002/cbic.201600192

文献信息

• A Lucifer-Based Environment-Sensitive Fluorescent PNA Probe for Imaging Poly(A) RNAs
  作者：Pramod M. Sabale、Uddhav B. Ambi、Seergazhi G. Srivatsan

  DOI：10.1002/cbic.201700661

  日期：2018.4.16

  Chasing tails: A PNA oligomer containing a new microenvironment‐sensitive fluorescent PNA base analogue, obtained by attaching the Lucifer chromophore (1,8‐naphthalimide) at the 5‐position of uracil, serves as a robust imaging tool for cellular poly(A) RNAs.

  追尾：一种 PNA 寡聚体，含有一种新的对微环境敏感的荧光 PNA 碱基类似物，通过将 Lucifer 发色团（1,8-萘酰亚胺）连接到尿嘧啶的 5 位而获得，可作为细胞聚 (A) 的强大成像工具RNA。
• Synthesis of New, Base-Modified PNA Monomers
  作者：Ferenc Sipos、Gyula Sági

  DOI：10.1080/15257770701490613

  日期：2007.11.26

  A number of N-Boc-protected peptide nucleic acids (PNA) monomers containing 5-aryl- and 5-alkynyl-uracil bases have been synthesized using different palladium-catalyzed cross-coupling reactions. Starting from the base-unprotected 5-iodo-uracil PNA monomer, only the Stille couplings were accomplished successfully, while Suzuki couplings with boronic acids containing the same aryl groups failed. During Sonogashira couplings with terminal alkynes, significant amounts of unrequired furano[2,3-d]pyrimidine by-products were formed. Protection of the lactam function by p-methoxybenzylation prevented the opportunity for intramolecular cyclization as well as formation of a negative charge on the 4-O atom, making it possible to reach almost quantitative yields at Sonogashira couplings and acceptable conversions in Suzuki reactions.
• The use of Sonogashira coupling for the synthesis of modified uracil peptide nucleic acid
  作者：Robert H.E Hudson、Ge Li、Joseph Tse

  DOI：10.1016/s0040-4039(02)00024-2

  日期：2002.2

  Palladium-catalyzed Sonogashira coupling has been shown to be compatible with PNA monomers as illustrated by the reaction of 5-iodouracil peptide nucleic acid monomer (U-1-PNA) with several terminal alkynes. These reactions hake been performed in the solution Phase and with U-1-PNA linked to an insoluble polymer Support. The results presented herein shock that while the isolated yields from the solution phase chemistry are modest (38 53%), the yields of the resin-bound Coupling reactions are essentially quantitative. at the monomer level. A selection of alkynes LIS used to install various additional functionality on the uracil nucleobase, Examples of a hydroxyl, protected thiol and protected amino group are given. Further, an example of derivatization of a resin-bound oligomer with a single U-1 insert is given. (C) 2002 Elsevier Science Ltd. All rights reserved.