2-(4-hydroxy-7-oxohept-5-enoyl)-1-palmitoyl-sn-glycero-3-phosphatidylcholine | 540742-93-6

• 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: 2-(4-hydroxy-7-oxohept-5-enoyl)-1-palmitoyl-sn-glycero-3-phosphatidylcholine
• 英文别名: (E)-2-(4-hydroxy-7-oxohept-5-enoyl)-1-palmitoyl-sn-glycero-3-phosphatidylcholine；Phoha-PC；[(2R)-3-hexadecanoyloxy-2-[(E)-4-hydroxy-7-oxohept-5-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 540742-93-6
• 化学式: C₃₁H₅₈NO₁₀P
• 分子量: 635.776
• InChiKey: JZEIFJXAJNJJFB-MATOFXKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  43
• 可旋转键数：
  31
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxy-7-oxohept-5-enoyl)-1-palmitoyl-sn-glycero-3-phosphatidylcholine 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 2.0h， 以71%的产率得到(4-hydroxy-6-carboxyhex-5-enoyl)-1-palmitoyl-2-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：

  2-呋喃丙酸乙酯 在 吡啶 、 N-甲基咪唑 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 Porcine pancreatic lipase type II 、 水 、 4-甲基苯磺酸吡啶 、 2,6-二氯苯甲酰氯 、 sodium chloride 、 calcium chloride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 27.0h， 生成 2-(4-hydroxy-7-oxohept-5-enoyl)-1-palmitoyl-sn-glycero-3-phosphatidylcholine
  参考文献：
  名称：

  2-溶血磷脂酰胆碱的γ-羟基-α,β-不饱和醛酯的有效合成

  摘要：

  γ-羟基链烯醛磷脂的多种生物活性及其与疾病的关系是深入研究的主题。磷脂醛，例如 2-溶血磷脂酰胆碱的 4-羟基-7-氧代庚烷-5-烯酸酯 (HOHA-PC)、2-溶血-磷脂酰胆碱的 5-羟基-8-氧代-6-辛烯酸酯PC (HOOA-PC) 和 2-lyso-PC 的 9-羟基-12-oxododec-10-烯酸酯 (HODA-PC) 是通过多不饱和脂肪酰基磷脂的氧化裂解产生的。为了促进对其化学和生物学的研究，我们现在报告了 HOOA、HODA 和 HOHA 磷脂的有效全合成。因为目标 γ-羟基烯醛很容易通过醛基氧化成羧酸或环化成呋喃而分解，

  DOI：

  10.1016/j.bmc.2010.10.058

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.
• An efficient synthesis of γ-hydroxy-α,β-unsaturated aldehydic esters of 2-lysophosphatidylcholine
  作者：Jaewoo Choi、James M. Laird、Robert G. Salomon

  DOI：10.1016/j.bmc.2010.10.058

  日期：2011.1

  4-hydroxy-7-oxohept-5-enoic acid ester of 2-lyso-phosphatidylcholine (HOHA-PC), the 5-hydroxy-8-oxo-6-octenoic acid ester of 2-lyso-PC (HOOA-PC), and the 9-hydroxy-12-oxododec-10-enoic acid ester of 2-lyso-PC (HODA-PC), are generated by oxidative cleavage of polyunsaturated fatty acyl phospholipids. To facilitate investigations of their chemistry and biology, we now report efficient total synthesis of HOOA, HODA

  γ-羟基链烯醛磷脂的多种生物活性及其与疾病的关系是深入研究的主题。磷脂醛，例如 2-溶血磷脂酰胆碱的 4-羟基-7-氧代庚烷-5-烯酸酯 (HOHA-PC)、2-溶血-磷脂酰胆碱的 5-羟基-8-氧代-6-辛烯酸酯PC (HOOA-PC) 和 2-lyso-PC 的 9-羟基-12-oxododec-10-烯酸酯 (HODA-PC) 是通过多不饱和脂肪酰基磷脂的氧化裂解产生的。为了促进对其化学和生物学的研究，我们现在报告了 HOOA、HODA 和 HOHA 磷脂的有效全合成。因为目标 γ-羟基烯醛很容易通过醛基氧化成羧酸或环化成呋喃而分解，