(2S)-3-[[(2R)-2-[12-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]dodecanoyloxy]-3-hexadecanoyloxypropoxy]-hydroxyphosphoryl]oxy-2-aminopropanoic acid | 1039801-29-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: (2S)-3-[[(2R)-2-[12-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]dodecanoyloxy]-3-hexadecanoyloxypropoxy]-hydroxyphosphoryl]oxy-2-aminopropanoic acid
• CAS: 1039801-29-0
• 化学式: C₄₄H₈₁N₄O₁₂PS
• 分子量: 921.186
• InChiKey: LXIPMDAAVGUIRH-FSBYBPBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  62
• 可旋转键数：
  43
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  267
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  (2R)-3-((((S)-3-(tert-butoxy)-2-((tert-butoxycarbonyl)amino)-3-oxopropoxy)(hydroxy)phosphoryl)oxy)-2-((12-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)dodecanoyl)oxy)propyl palmitate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以85%的产率得到(2S)-3-[[(2R)-2-[12-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]dodecanoyloxy]-3-hexadecanoyloxypropoxy]-hydroxyphosphoryl]oxy-2-aminopropanoic acid
  参考文献：
  名称：

  Bio-orthogonal Phosphatidylserine Conjugates for Delivery and Imaging Applications

  摘要：

  The syntheses of phosphatidylserine (PS) conjugates are described, including fluorescent derivatives for potential cellular delivery and bioimaging applications. Installation of terminal functional groups (amine, thiol, or alkyne) onto the sn-2 chain provides reactive sites for bio-orthogonal conjugation of cargo with suitably protected PS derivatives. An amine-containing PS forms amide bonds with peptidic cargo, a thiol derivative is designed for conjugation to cargo that contain alpha-halo carbonyls or Michael acceptors, and the terminal alkyne PS analogue permits "click" conjugation with any azide-tagged molecule. This latter conjugation method is quite versatile as it can be performed without PS headgroup protection, in aqueous media, and with acid-labile cargo.

  DOI：

  10.1021/jo8011336