Ac-Gly-Lys-OMe | 10236-44-9

• 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: N-acetyl-glycyl-L-lysine methyl ester acetate；N-Ac-Gly-L-Lys methyl ester；N-acetylglyin-L-lysine methyl ester；N-acetyl-glycine-L-lysine methyl ester；methyl 6-amino-2-((2-acetylamino)acetyl)amino hexanoate；N-acetylglycyllysine-O-methyl ester；N-Ac-Gly-L-Lys-OMe；Aglme；methyl (2S)-2-[(2-acetamidoacetyl)amino]-6-aminohexanoate
• CAS: 10236-44-9
• 化学式: C₁₁H₂₁N₃O₄
• 分子量: 259.305
• InChiKey: FIGKGJVUYAFLBI-VIFPVBQESA-N

物化性质

• 沸点：
  509.4±50.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

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

制备方法与用途

Ac-Gly-Lys-OMe是尿激酶的底物，也可用来评估小分子抑制剂对尿激酶活性的影响。

反应信息

• 作为反应物：
  描述：

  丙二醛 、 Ac-Gly-Lys-OMe 在 sodium acetate buffer 作用下， 反应 48.0h， 生成 1-[5-carboxymethyl-5-(N-acetylglycylamino)pentyl]-3-{1-[5-carboxymethyl-5-(N-acetylglycylamino)pentyl]-3,5-diformyl-1,4-dihydropyridin-4-yl}pyridinium
  参考文献：
  名称：

  A novel fluorescent malondialdehyde-lysine adduct

  摘要：

  We report a novel type of fluorescent product derived from the reaction of the lysine residue with malondialdehyde (MDA). When the lysine-containing peptide (N-acetyl-glycyl-L-lysine methyl ester) was treated with MDA prepared by the acid hydrolysis of 1,1,3,3-tetramethoxypropane, the main fluorescent product, which corresponded neither to the 1-amino-3-iminopropene derivative (2) nor to the 4-methyl-1,4-dihydro-3,5-dicarbaldehyde derivative (3), was detected by reverse-phase HPLC. By analysis of its UV, NMR, and high-resolution FAB mass spectra, it was confirmed to be 1-[5-carboxymethyl-5-(N-acetylglycylamino)pentyl]-3-[1-(5-carboxymethyl-5-(N-acetylglycylamino)-pentyl)-3,5-diformyl-1,4-dihydropyridin-4-yl]pyridinium (1). This finding may provide a new clue to the formation mechanisms of fluorescent lipofuscin-like pigment.

  DOI：

  10.1016/s0009-3084(96)02624-2

文献信息

• Synthesis and protein conjugation studies of vitamin K analogues
  作者：Richard J. Payne、Alison M. Daines、Bruce M. Clark、Andrew D. Abell

  DOI：10.1016/j.bmc.2004.08.037

  日期：2004.11

  Two vitamin K analogues bearing a carboxylic acid side chain (9a and its deuterated analogue 9b) were each synthesised in six steps from commercially available menadione. Analogue 9b was conjugated to lysozyme and bovine serum albumin (BSA) using EDCI/HOBT and by prior formation of its activated succinimidyl ester 11. Quantification of the thus formed conjugates by ESMS and LC-MS revealed that the

  两种带有羧酸侧链的维生素K类似物（9a和其氘代类似物9b）是从市售甲萘醌中分六步合成的。使用EDCI / HOBT并事先形成其活化的琥珀酰亚胺酯11，将类似物9b与溶菌酶和牛血清白蛋白（BSA）偶联。偶联中的α-淀粉酶系统地控制与蛋白质缀合的类似物的数量。
• Characterization of Adducts Formed in the Reactions of Methylglyoxal and Malonaldehyde with Lysine and Histidine Derivatives
  作者：Donata Pluskota-Karwatka、Agata Pawłowska

  DOI：10.1002/hlca.201400345

  日期：2015.6

  spectrum of reactions between these compounds and biomolecules, and gain insight into their mechanisms. In this study, we investigated the reactivity of endogenous α‐oxoaldehyde, methylglyoxal, and of malonaldehyde towards amino acid derivatives, and we identified new adducts with Nα‐acetyllysine and Nα‐acetylhistidine. In addition, we showed that a structurally analogous adduct is also formed with the

  人们认为，α-氧代醛（如甲基乙二醛）对生物聚合物的糖基化作用在与糖尿病和代谢性疾病相关的复杂病理学中起着重要作用。要设计可能干扰此类醛的内源性产生或促进其解毒的策略，或者开发出可以在细胞水平上抑制乙醛的有害作用的治疗方法，重要的是表征之间的广泛反应这些化合物和生物分子，并深入了解其机理。在这项研究中，我们调查的内源性的反应性α -oxoaldehyde，甲基乙二醛，丙二醛和朝向氨基酸衍生物，和我们确定了新的加合物与Ñ α-乙酰基和Ñ α -acetylhistidine。此外，我们表明，与模型肽N-乙酰基甘氨酸赖氨酸O-甲酯也形成了结构相似的加合物。表征的化合物最有可能是由于将研究的生物分子的适当亲核中心加到最初形成的醛偶联物的CC键上而得到的。生成的加合物含有一个亲电的β-二羰基部分，并可能参与DNA蛋白质或蛋白质交联的形成。
• The preparation of side chain functionalized analogues of coenzyme Q for protein conjugation studies
  作者：Alison M. Daines、Andrew D. Abell

  DOI：10.1039/b407659a

  日期：——

  The synthesis of two analogues of CoQ (10 and 13) suitable for conjugation to a peptide or protein, and hence the development of an ELISA immunoassay, is presented. These analogues were synthesized from the protected quinone, 1-bromo-2-methyl-3,4,5,6-tetramethoxybenzene (1), itself prepared from commercially available CoQ-0 (3). Model coupling studies of one of the analogues (10) to N-acetyl-L-lysine methyl ester and a lysine containing dipeptide (N-acetyl-glycine-L-lysine methyl ester) were also undertaken as a first step to monoclonial antibody production.

  本文介绍了两种适合与肽或蛋白质结合的辅酶Q（CoQ）类似物（10和13）的合成，以及ELISA免疫测定的发展。这些类似物是从保护的醌化合物1-溴-2-甲基-3,4,5,6-四甲氧基苯（1）合成的，而该化合物是从市售的CoQ-0（3）制备的。同时还进行了其中一种类似物（10）与N-乙酰-L-赖氨酸甲酯和含赖氨酸的二肽（N-乙酰甘氨酸-L-赖氨酸甲酯）的模型偶联研究，作为单克隆抗体生产的第一步。
• 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。
• 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。