[(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-heptadec-3-enyl]-methyl-carbamic acid tert-butyl ester | 709026-50-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-heptadec-3-enyl]-methyl-carbamic acid tert-butyl ester
• CAS: 709026-50-6
• 化学式: C₃₆H₇₅NO₄Si₂
• 分子量: 642.167
• InChiKey: QBXDVSLKSLYMGN-PGHHRUPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.89
• 重原子数：
  43.0
• 可旋转键数：
  20.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-heptadec-3-enyl]-methyl-carbamic acid tert-butyl ester 在 吡啶 、 四溴化碳 、 氢氟酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 [(E)-(1S,2R)-1-(Dimethoxy-phosphoryloxymethyl)-2-hydroxy-heptadec-3-enyl]-methyl-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Syntheses of sphingosine-1-phosphate analogues and their interaction with EDG/S1P receptors

  摘要：

  Sphingosine-I-phosphate (SIP) is an important regulator of a wide variety of biological processes acting as an endogenous ligand to EDG/S1P receptors. In an effort to establish structure-activity relationship between EDG/S1P and ligands, we report herein homology modeling study of EDG-1/S1P(1), syntheses of S I P analogues, and cell based binding affinity study for EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.001
• 作为产物：
  描述：

  N-叔丁氧羰基-赤式-鞘氨醇 在 咪唑 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-heptadec-3-enyl]-methyl-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Syntheses of sphingosine-1-phosphate analogues and their interaction with EDG/S1P receptors

  摘要：

  Sphingosine-I-phosphate (SIP) is an important regulator of a wide variety of biological processes acting as an endogenous ligand to EDG/S1P receptors. In an effort to establish structure-activity relationship between EDG/S1P and ligands, we report herein homology modeling study of EDG-1/S1P(1), syntheses of S I P analogues, and cell based binding affinity study for EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.001

文献信息

• Design, synthesis of ceramide 1-phosphate analogs and their affinity for cytosolic phospholipase A2 as evidenced by surface plasmon resonance
  作者：Tomokazu Yasuda、Daiki Ueura、Madoka Nakagomi、Shinya Hanashima、J. Peter Slotte、Michio Murata

  DOI：10.1016/j.bmcl.2024.129792

  日期：2024.7

  Ceramide 1-phosphate (C1P) is a lipid mediator that specifically binds and activates cytosolic phospholipase Aα (cPLAα). To elucidate the structure–activity relationship of the affinity of C1P for cPLAα in lipid environments, we prepared a series of C1P analogs containing structural modifications in the hydrophilic parts and subjected them to surface plasmon resonance (SPR). The results suggested the

  神经酰胺 1-磷酸 (C1P) 是一种脂质介质，可特异性结合并激活胞质磷脂酶 Aα (cPLAα)。为了阐明脂质环境中 C1P 对 cPLAα 亲和力的构效关系，我们制备了一系列亲水部分含有结构修饰的 C1P 类似物，并对它们进行表面等离子共振 (SPR)。结果表明，C1P 结构中的酰胺基、3-OH 基和磷酸基上存在 cPLAα 的特异性结合位点。特别是，二氢-C1P 对 cPLAα 表现出增强的亲和力，表明 3-羟基的氢键能力对于与 cPLAα 的相互作用很重要。这项研究有助于了解 C1P 的特定结构部分对原子水平上与 cPLAα 相互作用的影响，并可能有助于设计调节 cPLAα 激活的药物。