Ac-Gly-Lys-OMe

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ac-Gly-Lys-OMe
• 英文别名: Methyl 2-[(2-acetamidoacetyl)amino]-6-aminohexanoate
• 化学式: C₁₁H₂₁N₃O₄
• 分子量: 259.305
• InChiKey: FIGKGJVUYAFLBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ac-Gly-Lys-OMe 、 4,7-dioxoheptanoic acid 2-lysophosphatidylcholine ester 以 甲醇 为溶剂， 反应 8.0h， 以88%的产率得到
  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

• Substituted imidazolium salts and their use for the inhibition of protein ageing.
  申请人：ALTEON Inc.

  公开号：EP1213282A1

  公开（公告）日：2002-06-12

  The present invention relates to compositions and methods for inhibiting and reversing nonenzymatic cross-linking (protein ageing). Accordingly, compositions are disclosed which comprise substituted imidazolium compounds capable of inhibiting the formation of, as well as reversing already formed, advanced glycosylation end products of target proteins. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein ageing can be treated.

  本发明涉及用于抑制和逆转非酶交联（蛋白老化）的组合物和方法。因此，揭示了包括替代咪唑化合物的组合物，能够抑制目标蛋白质的高级糖基化终产物的形成，并逆转已经形成的高级糖基化终产物。该方法包括将目标蛋白质与该组合物接触。该发明可预见在工业和治疗应用中得到应用，因为可以治疗食物腐败和动物蛋白质老化。
• Bioactive 4-Oxoheptanedioic Monoamide Derivatives of Proteins and Ethanolaminephospholipids: Products of Docosahexaenoate Oxidation
  作者：Junhong Guo、Li Hong、Xiaoxia Z. West、Hua Wang、Robert G. Salomon

  DOI：10.1021/acs.chemrestox.6b00218

  日期：2016.10.17

  4-oxo-heptanedioic (OHdiA) monoamide derivatives, are present in vivo. However, whereas the anti-CEP antibody is highly specific and does not cross-react with the OHdiA monoamide epitope, the anti-OHdiA monoamide antibody cross-reacted with CEP epitopes making it of little value as an analytical tool for OHdiA monoamides but suggesting the possibility that OHdiA monoamides would exhibit receptor-mediated

  氧化应激导致生物分子的脂质衍生的氧化修饰，这种修饰涉及许多病理状态。含有多不饱和脂肪酸的磷脂是自由基引发氧化的主要目标。掺入二十二碳六烯酸酯（DHA）的磷脂高度丰富于重要的神经结构，包括大脑和视网膜，其中DHA分别占总脂肪酸的40％和60％。2-二十二碳六烯酰基-1-棕榈酰基-sn的氧化片段化-甘油磷酸胆碱与2-溶血磷脂酰胆碱，HOHA-PC和KOHA-PC生成4-羟基-7-氧庚基-5-烯酸（HOHA）和4-酮7-氧庚基-5-烯酸（KOHA）的酯。在人体肿瘤，视网膜和血液中用抗CEP抗体通过免疫学方法检测到在羧基乙基吡咯（CEP）衍生物中掺入蛋白质和乙醇胺磷脂的伯氨基的共价HOHA加合物。现在，我们生成了一种抗OHdiA抗体，以测试以下假设：体内存在4-羟基-庚二酮（OHdiA）单酰胺衍生物中包含蛋白质或乙醇胺磷脂的伯氨基的KOHA加合物。但是，尽管抗CEP抗体具有高度特异性，并且不会与O
• Substituted imidazoliums and methods of use therefor
  申请人：——

  公开号：US20040198795A1

  公开（公告）日：2004-10-07

  The present invention relates to compositions and methods for inhibiting and reversing nonenzymatic cross-linking (protein aging). Accordingly, compositions are disclosed which comprise substituted imidazolium compounds capable of inhibiting the formation of, as well as reversing already formed, advanced glycosylation endproducts of target proteins. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.

  本发明涉及用于抑制和逆转非酶交联（蛋白质老化）的组合物和方法。因此，揭示了包括取代咪唑化合物的组合物，其能够抑制目标蛋白质的高级糖基化终产物的形成，并逆转已经形成的高级糖基化终产物。该方法包括将目标蛋白质与该组合物接触。该发明可用于工业和治疗应用，因为可用于处理食品腐败和动物蛋白质老化。
• Reaction of <i>N</i>-Acetylglycyllysine Methyl Ester with 2-Alkenals:  An Alternative Model for Covalent Modification of Proteins
  作者：Andrew Baker、Lukáš Žídek、Don Wiesler、Josef Chmelík、Marty Pagel、Milos V. Novotny

  DOI：10.1021/tx970167e

  日期：1998.7.1

  2-hexenal. The reaction products were characterized through a combination of NMR and MS techniques. The structural elucidation efforts have shown the formation of pyridinium salts through the reaction of two or more alkenals with one amino group. Kinetic data were obtained using a continuous infusion of the reaction mixture into an electrospray ionization mass spectrometer. A mechanism is proposed that offers

  在脂质过氧化产物与蛋白质的各种反应中，已显示2-烯醛与赖氨酸残基的ε-氨基广泛反应[Zidek等人，J.Biol.Chem.Soc。，1992，6，1897]。（1997）Chem。Res。毒药。10，702-710]。为了获得有关该修饰的动力学和机理方面的其他信息，将模型肽（N-乙酰基甘氨酸赖氨酸O-甲酯）与2-己烯醛反应。通过NMR和MS技术的结合来表征反应产物。结构阐明的努力表明，通过两个或多个烯基与一个氨基的反应形成吡啶鎓盐。使用将反应混合物连续注入电喷雾电离质谱仪中获得动力学数据。提出了一种机制，该机制为形成稳定的蛋白质交联提供了另一种模型。反应通过席夫碱中间体进行以形成二氢吡啶物质，该二氢吡啶物质可被还原以形成各种3,4-或2,5-取代的吡啶鎓物质或与另一席夫碱反应以形成三烷基取代的吡啶鎓结构。与广泛接受的1：2相比，该结构（醛/胺）的化学计量比为3：2。因此，它代表了脂质过氧
• Stabilized plasminogen activator precursor and method of producing the same
  申请人：——

  公开号：EP0190041A3

  公开（公告）日：1988-09-28

  A plasminogen activator precursor obtainable from a serum-free culture fluid of human kidney cells is stabilized by adding to its solution a stabilizer selected from gelatin, poly-C1-C5-alkylene glycols, polyethylene-polyoxypropylene copolymers, mandelic acid salts, triethanolamine, acid addition salts of acetylglycyllysine methyl ester, guanidine salts, thiocyanic acid salts, alkali metal iodides and serine.

  在从人肾细胞无血清培养液中获得的纤溶酶原激活剂前体的溶液中加入一种稳定剂，该稳定剂选自明胶、聚-C1-C5-烷二醇、聚乙烯-聚氧丙烯共聚物、扁桃酸盐、三乙醇胺、乙酰甘氨酰甘氨酸甲酯的酸加成盐、胍盐、硫氰酸盐、碱金属碘化物和丝氨酸。