甘氨酰甘氨酸甲酯盐酸盐 | 2776-60-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 天然氨基酸及其衍生物
• 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
• 中文名称: 甘氨酰甘氨酸甲酯盐酸盐
• 英文名称: glycylglycine methyl ester hydrochloride
• 英文别名: methyl glycylglycinate hydrochloride；H-Gly-Gly-OMe*HCl；N-(glycyl)glycine methyl ester hydrochloride；methyl ((aminoacetyl)amino)acetate hydrochloride；gly-gly methyl ester hydrochloride；L-Glycyl-Glycine methyl ester hydrochloride；Gly-Gly-OMe*HCl；Methyl 2-(2-aminoacetamido)acetate hydrochloride；methyl 2-[(2-aminoacetyl)amino]acetate;hydrochloride
• CAS: 2776-60-5
• 化学式: C₅H₁₀N₂O₃*ClH
• mdl: MFCD00039056
• 分子量: 182.607
• InChiKey: RZOAGVGJBLVHIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.11
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  81.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2924199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  甘氨酰甘氨酸甲酯盐酸盐 在 氯仿 、 氨 作用下， 生成 triglycine methyl ester
  参考文献：
  名称：

  Sluyterman; Kooistra, Recueil des Travaux Chimiques des Pays-Bas, 1952, vol. 71, p. 277,278

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2-(2-phthalimidoacetamido)acetate 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 甘氨酰甘氨酸甲酯盐酸盐
  参考文献：
  名称：

  Novel thiazolidinedione-5-acetic-acid-peptide hybrid derivatives as potent antidiabetic and cardioprotective agents

  摘要：

  Thiazolidinediones (TZDs) are one of the important clinically established antidiabetic agents. Aminoacid and peptides have an advantage of better target selectivity and specificity. As hybrids, they also improved absorption and showed better bioavailability, which in turn makes them safer. Hence, here an effort has been made to synthesize hybrids of thiazolidinedione with amino-acids and peptides and evaluate their antidiabetic and cardioprotective effect in streptozotocin-nicotinamide (STZ-NA) induced Type 2 diabetes mellitus (T2DM) rat models.A series of 14 thiazolidinedione-5-acetic acid hybrids with of different amino-acids and peptide combinations were synthesized, characterized and further screened for antidiabetic and cardioprotective activity.Among all, six compounds T1 (SSDMA1), T4 (SSDMA4), T5 (SSDMA5), T7 (SDMA13), T9 (SSDMA15) and T13 (SSDMA49) showed better antioxidant activity and comparable % glucose uptake by yeast cells.Hence, the in vivo antidiabetic screening was done for these six compounds. Among all six T1, T7, T13 showed significant blood glucose level decrease compared to standard pioglitazone HCl. Also T1, T7 and T13 showed better antioxidant activity with lower IC50 value than standard ascorbic acid, and hence in vivo cardioprotective studies were done for these. The ECG studies showed that T1 (SSDMA1) and T7 (SSDMA13) were better effective than SDMA49 (T13) in restoring the normal functioning of the heart, thus may help in preventing the development of diabetic cardiomyopathy (DCM) and controlling T2DM. (C) C 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biopha.2017.01.160

文献信息

• Intermolecular Phosphoryl Transfer of N-Phosphoryl Amino Acids
  作者：Xiang Gao、Honggui Deng、Guo Tang、Yan Liu、Pengxiang Xu、Yufen Zhao

  DOI：10.1002/ejoc.201100234

  日期：2011.6

  National Natural Science Foundation of China (NSFC)[21075103, 20972130, 20805037, 20732004]

  国家自然科学基金(NSFC)[21075103, 20972130, 20805037, 20732004]
• Enhanced Mechanical and Helical Properties with Achiral Calix[4]arene in a Co-Assembled Hydrogel with a Helical Structure
  作者：Heekyoung Choi、Hyowon Seo、Misun Go、Shim Sung Lee、Jong Hwa Jung

  DOI：10.1002/ejoc.201701650

  日期：2018.1.17

  Co‐assembled hydrogel composed of 1A and 2G induced the remarkable enhancement of helical intensity and mechanical properties.

  由1A和2G组成的共组装水凝胶引起螺旋强度和机械性能的显着提高。
• Designed Semisynthetic Protein Inhibitors of Ub/Ubl E1 Activating Enzymes
  作者：Xuequan Lu、Shaun K. Olsen、Allan D. Capili、Justin S. Cisar、Christopher D. Lima、Derek S. Tan

  DOI：10.1021/ja9088549

  日期：2010.2.17

  mechanism-based protein inhibitors of ubiquitin (Ub) and ubiquitin-like modifier (Ubl) activating enzymes (E1s) have been developed to target E1-catalyzed adenylation and thioesterification of the Ub/Ubl C-terminus during the processes of protein SUMOylation and ubiquitination. The inhibitors were generated by intein-mediated expressed protein ligation using a truncated Ub/Ubl protein (SUMO residues

  泛素 (Ub) 和泛素样修饰剂 (Ubl) 激活酶 (E1s) 的半合成、基于机制的蛋白质抑制剂已被开发用于在蛋白质 SUMOylation 过程中靶向 E1 催化的 Ub/Ubl C 末端的腺苷酸化和硫酯化和泛素化。抑制剂是通过内含肽介导的表达蛋白连接产生的，使用截断的 Ub/Ubl 蛋白（SUMO 残基 1-94；Ub 残基 1-71）与 C 端硫酯和合成三肽具有 C 端腺苷类似物和 N -末端半胱氨酸残基。SUMO-AMSN (4a) 和 Ub-AMSN (4b) 含有磺酰胺基团作为前半反应中同源 Ub/Ubl-AMP 腺苷酸中间体中磷酸基团的不可水解模拟物，这些构建体选择性地抑制 SUMO E1 和Ub E1 分别呈剂量依赖性。SUMO-AVSN (5a) 和 Ub-AVSN (5b) 含有亲电子乙烯基磺酰胺，旨在在第二个半反应中捕获传入的 E1 半胱氨酸亲核试剂（SUMO E1 中的
• Epimerization-Free Block Synthesis of Peptides from Thioacids and Amines with the Sanger and Mukaiyama Reagents
  作者：David Crich、Indrajeet Sharma

  DOI：10.1002/anie.200805782

  日期：2009.3.16

  reaction of C‐terminal thioacids derived from protected amino acids and peptides with the Sanger reagent and other electron‐deficient aryl halides in the presence of a free amine immediately form a peptide bond with the amine. This essentially epimerization‐free method was used for the 4+4 block synthesis of a hindered octapeptide (see scheme; Boc, Pbf, and Trt are protecting groups).

  在游离胺存在下，由受保护氨基酸和肽衍生的C末端硫代酸与Sanger试剂和其他电子不足的芳基卤化物快速反应而形成的高活化硫酯立即与胺形成肽键。该基本无差向异构的方法用于受阻八肽的4 + 4嵌段合成（请参阅方案； Boc，Pbf和Trt是保护基）。
• Design, synthesis, insecticidal evaluation and molecular docking studies of cis-nitenpyram analogues bearing diglycine esters
  作者：YanXia Chen、ChuanWen Sun、XiaXia Wen、WangGeng Zhang

  DOI：10.1007/s11426-012-4748-x

  日期：2013.2

  mg/L. Among these analogues, 6b showed 100% mortality against Nilaparvata lugens (LC50 = 0.163 mg/L) and 90% against Aphis medicagini at 4 mg/L. SARs suggested that the insecticidal potency of our designed cis-nitenpyram analogues was dual-controlled by the size and species of the ester groups. The molecular docking simulations revealed that the structural uniqueness of these analogues may lead to a unique

  基于受体结构指导的新烟碱设计策略，设计并合成了一系列带有二甘氨酸酯的新型顺式-硝苯并吡喃类似物。初步的生物分析表明，与我们以前的工作相比，目标化合物的杀虫谱得到了扩展，而所有目标化合物在100 mg / L的浓度下均对Lupas lugens和Aphis medicagini表现出优异的杀虫活性。在这些类似物中，6b的抗褐飞虱死亡率为100％（LC 50 = 0.163 mg / L），抗药性的蚜虫为90％（4 mg / L）。特区建议，我们设计的顺式的杀虫效力-nitenpyram类似物受酯基团的大小和种类双重控制。分子对接模拟显示，与先前设计的化合物相比，这些类似物的结构独特性可能导致独特的分子识别和结合模式。肽键的引入在与昆虫nAChRs的氨基酸残基键合的乙炔吡喃类似物之间产生了更重要的氢键。对接结果解释了在体外观察到的SAR ，并阐明了这些顺式-硝苯并吡喃类似物的新型杀虫机理。