3-[3-(Butyldisulfanyl)propoxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 英文名称: 3-[3-(Butyldisulfanyl)propoxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• 英文别名: 3-[3-(butyldisulfanyl)propoxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• 化学式: C₁₆H₃₃N₂O₂PS₂
• 分子量: 380.6
• InChiKey: OBTPMKUUPKAKHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  96.1
• 氢给体数：
  0
• 氢受体数：
  6

文献信息

• Dithiolane Based Thiol Modifier For Labeling and Stronger Immobilization of Bio-Molecules On Solid Surfaces
  申请人：ChemGenes Corporation

  公开号：US20140142253A1

  公开（公告）日：2014-05-22

  The thiol modified oligonucleotides have vast number of applications in the field of nucleic acid chemistry. The conjugates generated by mono thiol groups are unstable at higher temperature, in high salt concentration buffers and in presence other thiols. There is strong need to develop a novel thiol modifier probes that can generate multiple thiol groups. Described herein are efficient processes and compounds, dithiolane phosphoramidites derivative and dithiolane succinyl supports. The advantage of our cyclic disulfide thiol modifier is multifold a) each incorporation introduces two thiol groups; b) it can be introduced at any desired site of oligonucleotides; c) The symmetrical branching nature of the spacer in the linker arm of dithiolane allows for clean oligo synthesis, where cleavage of the linker arm and thereby of loss of oligo chain is prevented. We have successfully made 20-mer oligonucleotide containing single dithiolane derivative at 3′, and 21-mer oligonucleotides containing single dithiolane derivative at 5′ or in the middle of the mixed base sequence. HPLC and ESI MS analysis of these oligonucleotides indicated satisfactory purity and correct composition of these oligos, respectively.

  巯基修饰的寡核苷酸在核酸化学领域有广泛的应用。单巯基基团生成的共轭物在高温、高盐浓度缓冲液和存在其他巯基的情况下不稳定。因此，有必要开发一种能够生成多个巯基基团的新型巯基修饰探针。本文描述了高效的工艺和化合物，包括二硫杂环磷酰胺衍生物和二硫杂环琥珀酰基支持体。我们的环状二硫化物巯基修饰的优点是多方面的：a)每个插入点引入两个巯基基团；b)它可以在寡核苷酸的任何所需位置引入；c)二硫杂环中链臂的对称分支性质允许进行干净的寡核苷酸合成，避免链臂的断裂和寡核苷酸链的损失。我们成功地制备了包含单个二硫杂环衍生物的20-mer寡核苷酸，在3'端，以及包含单个二硫杂环衍生物的21-mer寡核苷酸，在5'端或混合碱基序列的中间。这些寡核苷酸的HPLC和ESI MS分析表明它们的纯度和组成正确。
• US9441002B2
  申请人：——

  公开号：US9441002B2

  公开（公告）日：2016-09-13