N--3-(2-pyridyldithio)propionate | 221015-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并-1,2,3-三嗪类化合物
• 英文名称: N--3-(2-pyridyldithio)propionate
• 英文别名: N-[O-1,2,3-benzotriazin-4(3H)one-yl]-3-(2-pyridyldithio)propionate；BPDP；(4-Oxo-1,2,3-benzotriazin-3-yl) 3-(pyridin-2-yldisulfanyl)propanoate
• CAS: 221015-33-4
• 化学式: C₁₅H₁₂N₄O₃S₂
• 分子量: 360.417
• InChiKey: OROQWAZBNVZRJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  双十八烷基胺 、 N--3-(2-pyridyldithio)propionate 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以82%的产率得到N,N-Dioctadecyl-3-(pyridin-2-yldisulfanyl)-propionamide
  参考文献：
  名称：

  N-[O-1,2,3-benzotriazin-4(3H)one-yl]-3,(2-pyridyldithio)propionate: A more reactive alternative to SPDP

  摘要：

  N-[O-1,2,3-Benzotriazin-4(3H)one-yl]-3-(2-pyridyldithio)propionate [BPDP] has been synthesized and found to react with secondary amines to give high yields of acylated product. In sharp contrast, the widely used heterobifunctional coupling reagent, N-[O-succinimdyl]-3-(2-pyridyldithio) propionate [SPDP] afforded low to negligible yields of product. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02593-3
• 作为产物：
  描述：

  3-(2-吡啶二硫代)丙酸 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以61%的产率得到N--3-(2-pyridyldithio)propionate
  参考文献：
  名称：

  分子伞跨双层运动的化学证据

  摘要：

  已经获得了双壁和四壁分子伞在源自 1-palmitoyl-2-oleyol-sn-glycero-3-phoshatidylglycerol (POPG) 的大单层囊泡 (200 nm) 中跨双层运动的化学证据。通过 N1,N3-亚精双 [胆酸酰胺] (3) 与 [N-1, 2,3-苯并三嗪-4(3H)one-yl]-3-(2-pyridyldithio)propionate [BPDP]。还通过将 Fmoc 保护的亚氨基二乙酸与两个分子的 3 缩合，将仲氨基脱保护，并将所得中间体 (4) 与 BPDP 偶联来制备类似的四壁伞形 (2)。囊泡结合 1 与外部谷胱甘肽 (GSH) 的反应导致 2-MP 的快速和定量释放。

  DOI：

  10.1021/ja9904641

文献信息

• Lipid Raft Formation: Key Role of Polyunsaturated Phospholipids
  作者：Chang Wang、Yuming Yu、Steven L. Regen

  DOI：10.1002/anie.201611367

  日期：2017.2

  liquid‐disordered bilayers can be much stronger than the attractive forces between this same sterol and an exchangeable mimic of a high‐melting phospholipid in liquid‐ordered bilayers. We conclude that polyunsaturated phospholipids have been largely overlooked as major players in lipid raft formation. This knowledge should stimulate considerable interest in controlling the levels of polyunsaturated phospholipids

  导致脂质筏形成的力量了解甚少。迄今为止，大多数注意力都集中在胆固醇和高熔点脂质之间的有吸引力的相互作用上。排斥力很少受到关注。在这里，我们表明，胆固醇的可交换模拟物与液体无序双层中低熔点磷脂的可交换模拟物之间的排斥性相互作用比同一种固醇和高熔点磷脂的可交换模拟物之间的吸引力要强得多。在液体有序双层中。我们得出的结论是，多不饱和磷脂已被广泛视为脂质筏形成的主要参与者。该知识应引起人们对于控制多不饱和磷脂水平以使细胞膜正常发挥功能的兴趣。
• Sorting of Lipidated Peptides in Fluid Bilayers: A Molecular-Level Investigation
  作者：Trevor A. Daly、Paulo F. Almeida、Steven L. Regen

  DOI：10.1021/ja3074825

  日期：2012.10.17

  Nearest-neighbor recognition (NNR) measurements have been made for two lipidated forms of GlyCys, interacting with analogues of cholesterol and 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) in the liquid-ordered (l(o)) and liquid-disordered (l(d)) phases. Interaction free energies that have been determined from these measurements have been used in Monte Carlo simulations to quantify the distribution of the peptides between liquid-ordered and liquid-disordered regions. These simulations have shown that significant differences in the lipid chains have a very weak influence on the partitioning of the peptide between these two phases. They have also revealed an insensitivity of the peptide partition coefficient, K-p, to the size of the l(o) and l(d) domains that are present. In a broader context, these findings strongly suggest that the sorting of peripheral proteins in cellular membranes via differential lipidation may be more subtle than previously thought.
• Is the Linkage Region of Sphingolipids Responsible for Lipid Raft Formation?
  作者：Maki Uragami、Nobuya Tokutake、Xun Yan、Steven L. Regen

  DOI：10.1021/ja015715w

  日期：2001.5.1
• The Importance of Acyl Chain Placement on Phospholipid Mixing in the Physiologically Relevant Fluid Phase
  作者：Michihiro Sugahara、Maki Uragami、Nobuya Tokutake、Steven L. Regen

  DOI：10.1021/ja005811h

  日期：2001.3.1
• Chemical Evidence for Transbilayer Movement of Molecular Umbrellas
  作者：Sarinya Shawaphun、Vaclav Janout、Steven L. Regen

  DOI：10.1021/ja9904641

  日期：1999.6.1

  Chemical evidence has been obtained for transbilayer movement of a di-walled and a tetra-walled molecular umbrella in large unilamellar vesicles (200 nm) derived from 1-palmitoyl-2-oleyol-sn-glycero-3-phoshatidylglycerol (POPG). A di-walled molecular umbrella (1), bearing 2-mercaptopyridine (2-MP) as a “reactive tag”, was synthesized by reaction of N1,N3-spermidinebis[cholic acid amide] (3) with [N-1

  已经获得了双壁和四壁分子伞在源自 1-palmitoyl-2-oleyol-sn-glycero-3-phoshatidylglycerol (POPG) 的大单层囊泡 (200 nm) 中跨双层运动的化学证据。通过 N1,N3-亚精双 [胆酸酰胺] (3) 与 [N-1, 2,3-苯并三嗪-4(3H)one-yl]-3-(2-pyridyldithio)propionate [BPDP]。还通过将 Fmoc 保护的亚氨基二乙酸与两个分子的 3 缩合，将仲氨基脱保护，并将所得中间体 (4) 与 BPDP 偶联来制备类似的四壁伞形 (2)。囊泡结合 1 与外部谷胱甘肽 (GSH) 的反应导致 2-MP 的快速和定量释放。