1-palmitoyl-2-(4-pentenoyl)-sn-glycero-3-phosphatidylcholine

• 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: 1-palmitoyl-2-(4-pentenoyl)-sn-glycero-3-phosphatidylcholine
• 英文别名: 1-hexadecanoyl-2-(4E-valeryl)-sn-glycero-3-phosphocholine；[(2R)-3-hexadecanoyloxy-2-pent-4-enoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• 化学式: C₂₉H₅₆NO₈P
• 分子量: 577.739
• InChiKey: SOZUKXUDKQAUFE-HHHXNRCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  39
• 可旋转键数：
  29
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-palmitoyl-2-(4-pentenoyl)-sn-glycero-3-phosphatidylcholine 在 臭氧 、 二甲基硫 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以100%的产率得到2-(4-oxobutyryl)-1-palmitoyl-sn-glycero-3-phosphatidylcholine
  参考文献：
  名称：

  Oxidatively Truncated Docosahexaenoate Phospholipids:  Total Synthesis, Generation, and Peptide Adduction Chemistry

  摘要：

  The recent immunological detection of extraordinarily high levels of carboxyethylpyrrole (CEP) modifications of proteins from the retinas of individuals with age-related macular degeneration provided presumptive evidence for the involvement of docosahexaenoate-derived oxidatively truncated phospholipids in retinal pathology. To facilitate the in vivo detection and characterization of the chemistry and biological activities of these postulated naturally occurring molecules, a family of oxidatively truncated phospholipids was prepared by total syntheses. Their formation in oxidation reactions of a docosahexaenoate ester of 2-lysophosphatidylcholine (DHA-PC) was also demonstrated. Free radical-induced oxidative cleavage of DHA-PC promoted by myeloperoxidase or copper ions generates similar mixtures of these phospholipids. The most abundant products were 1-palmitoyl-2-succinoyl-sn-glycero-3-phosphatidylcholine (4.7%) and 2-(6-carboxy-4-oxohex-5-enoyl)-1-palmitoylsn-glycero-3-phosphatidylcholine (1.7%). Both of these oxidatively truncated phospholipids are homologues of biologically active arachidonate-derived phospholipids. A minor product from DHA-PC, 2-(4-hydroxy-7-oxohept-5-enoyl)-1-palmitoyl-sn-glycero-3-phosphatidylcholine (0.4% yield), reacted with the 6-amino group of a peptide lysyl residue to produce a CEP derivative in 0.7% yield. These observations support the previous conclusion, based on immunological evidence, that CEPs are generated by the reaction of an oxidatively truncated phospholipid with proteins in the retina and further indicate that CEP protein modifications probably represent only a tiny fraction of the products generated upon oxidative damage of DHA-PC in photoreceptor disk membranes.

  DOI：

  10.1021/jo026721t
• 作为产物：
  描述：

  4-戊烯酸 、 溶血磷脂酰胆碱(鸡蛋) 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 72.0h， 以90%的产率得到1-palmitoyl-2-(4-pentenoyl)-sn-glycero-3-phosphatidylcholine
  参考文献：
  名称：

  Oxidatively Truncated Docosahexaenoate Phospholipids:  Total Synthesis, Generation, and Peptide Adduction Chemistry

  摘要：

  The recent immunological detection of extraordinarily high levels of carboxyethylpyrrole (CEP) modifications of proteins from the retinas of individuals with age-related macular degeneration provided presumptive evidence for the involvement of docosahexaenoate-derived oxidatively truncated phospholipids in retinal pathology. To facilitate the in vivo detection and characterization of the chemistry and biological activities of these postulated naturally occurring molecules, a family of oxidatively truncated phospholipids was prepared by total syntheses. Their formation in oxidation reactions of a docosahexaenoate ester of 2-lysophosphatidylcholine (DHA-PC) was also demonstrated. Free radical-induced oxidative cleavage of DHA-PC promoted by myeloperoxidase or copper ions generates similar mixtures of these phospholipids. The most abundant products were 1-palmitoyl-2-succinoyl-sn-glycero-3-phosphatidylcholine (4.7%) and 2-(6-carboxy-4-oxohex-5-enoyl)-1-palmitoylsn-glycero-3-phosphatidylcholine (1.7%). Both of these oxidatively truncated phospholipids are homologues of biologically active arachidonate-derived phospholipids. A minor product from DHA-PC, 2-(4-hydroxy-7-oxohept-5-enoyl)-1-palmitoyl-sn-glycero-3-phosphatidylcholine (0.4% yield), reacted with the 6-amino group of a peptide lysyl residue to produce a CEP derivative in 0.7% yield. These observations support the previous conclusion, based on immunological evidence, that CEPs are generated by the reaction of an oxidatively truncated phospholipid with proteins in the retina and further indicate that CEP protein modifications probably represent only a tiny fraction of the products generated upon oxidative damage of DHA-PC in photoreceptor disk membranes.

  DOI：

  10.1021/jo026721t

文献信息

• Oxidatively Truncated Docosahexaenoate Phospholipids:  Total Synthesis, Generation, and Peptide Adduction Chemistry
  作者：Xiaorong Gu、Mingjiang Sun、Bogdan Gugiu、Stanley Hazen、John W. Crabb、Robert G. Salomon

  DOI：10.1021/jo026721t

  日期：2003.5.1

  The recent immunological detection of extraordinarily high levels of carboxyethylpyrrole (CEP) modifications of proteins from the retinas of individuals with age-related macular degeneration provided presumptive evidence for the involvement of docosahexaenoate-derived oxidatively truncated phospholipids in retinal pathology. To facilitate the in vivo detection and characterization of the chemistry and biological activities of these postulated naturally occurring molecules, a family of oxidatively truncated phospholipids was prepared by total syntheses. Their formation in oxidation reactions of a docosahexaenoate ester of 2-lysophosphatidylcholine (DHA-PC) was also demonstrated. Free radical-induced oxidative cleavage of DHA-PC promoted by myeloperoxidase or copper ions generates similar mixtures of these phospholipids. The most abundant products were 1-palmitoyl-2-succinoyl-sn-glycero-3-phosphatidylcholine (4.7%) and 2-(6-carboxy-4-oxohex-5-enoyl)-1-palmitoylsn-glycero-3-phosphatidylcholine (1.7%). Both of these oxidatively truncated phospholipids are homologues of biologically active arachidonate-derived phospholipids. A minor product from DHA-PC, 2-(4-hydroxy-7-oxohept-5-enoyl)-1-palmitoyl-sn-glycero-3-phosphatidylcholine (0.4% yield), reacted with the 6-amino group of a peptide lysyl residue to produce a CEP derivative in 0.7% yield. These observations support the previous conclusion, based on immunological evidence, that CEPs are generated by the reaction of an oxidatively truncated phospholipid with proteins in the retina and further indicate that CEP protein modifications probably represent only a tiny fraction of the products generated upon oxidative damage of DHA-PC in photoreceptor disk membranes.