(R)-N-(3-(dimethylamino)propyl)-5-(1,2-dithiolan-3-yl)pentanamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: (R)-N-(3-(dimethylamino)propyl)-5-(1,2-dithiolan-3-yl)pentanamide
• 英文别名: N-[3-(Dimethylamino)propyl]-5-[(3R)-1,2-dithiolan-3-YL]pentanamide；N-[3-(dimethylamino)propyl]-5-[(3R)-dithiolan-3-yl]pentanamide
• 化学式: C₁₃H₂₆N₂OS₂
• 分子量: 290.494
• InChiKey: WYBNMZHYWGSLQG-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-N-(3-(dimethylamino)propyl)-5-(1,2-dithiolan-3-yl)pentanamide 、 氯乙酸乙酯 以 四氢呋喃 为溶剂， 以86%的产率得到(R)-3-(5-(1,2-dithiolan-3-yl)pentanamido)-N-(2-ethoxy-2-oxoethyl)-N,N-dimethylpropan-1-aminium chloride
  参考文献：
  名称：

  pH-Switchable Interaction of a Carboxybetaine Ester-Based SAM with DNA and Gold Nanoparticles

  摘要：

  We describe a self-assembled monolayer (SAM) on a gold surface with a carboxybetaine ester functionality to control the interaction between DNA and gold nanoparticles via pH. The negatively charged phosphate backbone of DNA interacts with and adsorbs to the positively charged carboxybetaine esters on the SAM. DNA release can be achieved by the hydrolysis of carboxybetaine ester (CBE) to a zwitterionic carboxybetaine state. Furthermore, the adsorption of negatively charged citrate-capped gold nanoparticles to a SAM-modified plain gold surface can be controlled by the pH. The SAM based oh carboxybetaine ester allows for the homogeneous adsorption of particles, whereas the SAM after hydrolysis at high pH repels AuNP adsorption. The antifouling surface properties of the surface modified with carboxybetaine were investigated with protein samples.

  DOI：

  10.1021/acs.langmuir.7b00568
• 作为产物：
  描述：

  N,N-二甲基-1,3-二氨基丙烷 、 R-(+)-硫辛酸 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以57%的产率得到(R)-N-(3-(dimethylamino)propyl)-5-(1,2-dithiolan-3-yl)pentanamide
  参考文献：
  名称：

  pH-Switchable Interaction of a Carboxybetaine Ester-Based SAM with DNA and Gold Nanoparticles

  摘要：

  We describe a self-assembled monolayer (SAM) on a gold surface with a carboxybetaine ester functionality to control the interaction between DNA and gold nanoparticles via pH. The negatively charged phosphate backbone of DNA interacts with and adsorbs to the positively charged carboxybetaine esters on the SAM. DNA release can be achieved by the hydrolysis of carboxybetaine ester (CBE) to a zwitterionic carboxybetaine state. Furthermore, the adsorption of negatively charged citrate-capped gold nanoparticles to a SAM-modified plain gold surface can be controlled by the pH. The SAM based oh carboxybetaine ester allows for the homogeneous adsorption of particles, whereas the SAM after hydrolysis at high pH repels AuNP adsorption. The antifouling surface properties of the surface modified with carboxybetaine were investigated with protein samples.

  DOI：

  10.1021/acs.langmuir.7b00568