HCl*Gly-Gly-Gly-OMe | 39692-67-6

• 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: HCl*Gly-Gly-Gly-OMe
• 英文别名: glycylglycylglycine methyl ester hydrochloride；Diglycyl-glycine methyl ester hydrochloride；[2-[[2-[(2-methoxy-2-oxoethyl)amino]-2-oxoethyl]amino]-2-oxoethyl]azanium;chloride
• CAS: 39692-67-6
• 化学式: C₇H₁₃N₃O₄*ClH
• 分子量: 239.659
• InChiKey: FJUSXXACYFTVKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.23
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  HCl*Gly-Gly-Gly-OMe 在 N-甲基吗啉 、 sodium hydroxide 、 tris(4-bromophenyl)ammoniumyl stibanate 、 碳酸氢钠 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 生成 N-(tert-butyloxycarbonyl)hemicystinyl1->S₆>-glycyl-glycyl-glycyl-phenylalanyl-hemicystinyl6->S₁> methyl ester
  参考文献：
  名称：

  Platen, Martin; Steckhan, Eberhard, Liebigs Annalen der Chemie, 1984, # 9, p. 1563 - 1576

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2-(2-phthalimidoacetamido)acetate 在 乙醇 、 五氯化磷 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 HCl*Gly-Gly-Gly-OMe
  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

• Direct Amidation of Aldoses and Decarboxylative Amidation of α-Keto Acids: An Efficient Conjugation Method for Unprotected Carbohydrate Molecules
  作者：Chia-Ching Cho、Jia-Nan Liu、Chung-Hsun Chien、Jiun-Jie Shie、Ying-Chu Chen、Jim-Min Fang

  DOI：10.1021/jo802338k

  日期：2009.2.20

  With use of iodine as an appropriate oxidant, unprotected and unmodified aldoses undergo oxidative amidation with a variety of functionalized amines, α-amino esters, and peptides, whereas KDO, sialic acid, and other α-keto acids proceed with oxidative decarboxylation followed by in situ amidation. Glycoside bond and many other functional groups are inert under such mild reaction conditions. This reaction

  通过使用碘作为适当的氧化剂，未保护和未修饰的醛糖会与各种功能化的胺，α-氨基酯和肽进行氧化酰胺化，而KDO，唾液酸和其他α-酮酸会继续进行氧化脱羧反应原位酰胺化。在这种温和的反应条件下，糖苷键和许多其他官能团是惰性的。用于糖分子的直接连接的该反应方案在糖缀合物的一般和有效合成的发展中看起来是有希望的。
• One-Pot Ring-Opening Peptide Synthesis Using α,α-Difluoro-β-Lactams
  作者：Masaaki Omote、Atsushi Tarui、Masakazu Ueo、Marino Morikawa、Masahiko Tsuta、Sumika Iwasaki、Noriko Morishita、Yukiko Karuo、Kazuyuki Sato、Kentaro Kawai

  DOI：10.1055/s-0040-1707238

  日期：2020.12

  Abstract α,α-Difluoro-β-lactams successfully underwent ring-opening aminolysis with various amino acids in 2,2,2-trifluoroethanol to afford fluorine-containing peptides. In this aminolysis, it was found that 2,2,2-trifluoroethanol first attacked the α,α-difluoro-β-lactams with cleavage of lactam ring to form the corresponding open-chain 2,2,2-trifluoroethyl esters as reactive intermediates. The trifluoroethyl

  摘要 α，α-二氟-β-内酰胺成功地在2,2,2-三氟乙醇中进行了各种氨基酸的开环氨解反应，得到了含氟肽。在该氨解中，发现2,2,2-三氟乙醇首先通过裂解内酰胺环攻击α，α-二氟-β-内酰胺形成相应的开链2,2,2-三氟乙基酯作为反应性中间体。与相应的甲酯相比，三氟乙基酯更具亲电性，从而加速了各种氨基酸的氨解反应，形成了具有α，α-二氟亚甲基单元的β-氨基酸肽。
• TOLL-LIKE RECEPTOR-7 AND -8 MODULATORY 1H IMIDAZOQUINOLINE DERIVED COMPOUNDS
  申请人：David Sunil A.

  公开号：US20120294885A1

  公开（公告）日：2012-11-22

  The present disclosure provides novel imidazoquinoline derived compounds, derivatives thereof, analogues thereof, and pharmaceutically acceptable salts thereof, and methods of making and using such compounds. The present disclosure also provides TLR7 agonists and TLR7/TLR8 dual agonists, probes, tissue-specific molecules, adjuvants, immunogenic compositions, therapeutic compositions, and self-adjuvanting vaccines including the imidazoquinoline derived compounds, derivatives thereof, analogues thereof, and pharmaceutically acceptable salts thereof. Derivatives of the imidazoquinoline derived compounds also include dendrimers and dimers of the imidazoquinoline derived compounds, and methods of making and using the dendrimeic and dimeric imidazoquinoline derived compounds. The present disclosure also provides dual TLR2/TLR7 hybrid agonists that include imidazoquinoline derived compounds of the present disclosure.

  本公开提供了新型咪唑喹啉衍生化合物，其衍生物，类似物，以及其药用盐，并提供了制备和使用这些化合物的方法。本公开还提供了TLR7激动剂和TLR7/TLR8双激动剂，探针，组织特异性分子，佐剂，免疫原性组合物，治疗组合物，以及包括咪唑喹啉衍生化合物，其衍生物，类似物和药用盐的自佐剂疫苗。咪唑喹啉衍生化合物的衍生物还包括咪唑喹啉衍生化合物的树枝状分子和二聚体，以及制备和使用这些树枝状和二聚体咪唑喹啉衍生化合物的方法。本公开还提供了包括本公开的咪唑喹啉衍生化合物的双TLR2/TLR7混合激动剂。
• Carbonyl-Komplexe von Chrom, Molybdän und Wolfram mit Isocyanacetat. Reaktionen am koordinierten Isocyanacetat. Stabilisierung von Isocyanessigsäure und Isocyanacetylchlorid am Metall. Isocyanopeptide [1]
  作者：Dagobert Achatz、Markus A. Lang、Alfons Völkl、Wolf Peter Fehlhammer、Wolfgang Beck

  DOI：10.1002/zaac.200500256

  日期：2005.9

  Carbonyl Complexes of Chromium, Molybdenum and Tungsten with Isocyano Acetate. Reactions of Coordinated Isocyanoacetate. Stabilization of Isocyanoacetic Acid and Isocyanoacetyl Chloride at the Metal Atom. Isocyanopeptides The reactions of [(OC)5MCNCH2CO2Et] (M = Cr, W) with Na[N(SiMe3)2] or with KOH afford the isocyanoacetate complexes [(OC)5MCNCH2CO2]− (1,2). Similarly, the complex [(OC)3Mo(CNCH2CO2−Li+)3]

  铬、钼和钨与异氰乙酸酯的羰基配合物。配位异氰乙酸酯的反应。在金属原子上稳定异氰乙酸和异氰乙酰氯。异氰肽 [(OC)5MCNCH2CO2Et] (M = Cr, W) 与 Na[N(SiMe3)2] 或与 KOH 的反应得到异氰基乙酸盐复合物 [(OC)5MCNCH2CO2]- (1,2)。类似地，从[(OC)3Mo(CNCH2CO2Et)3](3)和LiOH得到复合物[(OC)3Mo(CNCH2CO2-Li+)3](4)。1 和 2 的质子化提供了可升华的异氰乙酸配合物 [(OC)5MCNCH2CO2H] (5, 6; M = Cr, W)，其中官能异氰化物稳定在金属原子上。[(OC)5WCNCH2CO2-K+] 和 [(OC)3Mo(CNCH2CO2-Li+)3] 与草酰氯反应生成异氰基乙酰氯化合物 [(OC)5WCNCH2COCl] (9)（可升华）和 [(OC)3Mo (CNCH2C
• Catalytic Formation of Oligopeptides from α-Amino Acid Esters with (p-Cymene)ruthenium(II) Complexes
  作者：Winfried Hoffmüller、Michael Maurus、Kay Severin、Wolfgang Beck

  DOI：10.1002/(sici)1099-0682(199806)1998:6<729::aid-ejic729>3.0.co;2-m

  日期：1998.6

  Consecutive addition of one-equivalent portions of glycine ethyl ester to [(p-cymene)Ru(GGGOMe−H+)Cl] leads to considerable amounts of (tetra- to nonapeptide)ruthenium complexes in a one-pot reaction, in which the (p-cymene)RuCl fragment acts as a catalyst. The analogous reaction with alanine methyl ester affords AGGG and AAGGG complexes as the main products. The course of these metal-catalyzed peptide

  将一当量的甘氨酸乙酯连续添加到 [(p-cymene)Ru(GGGOMe-H+)Cl] 中会在一锅反应中产生大量的（四到九肽）钌络合物，其中（ p-cymene)RuCl 片段作为催化剂。与丙氨酸甲酯的类似反应得到 AGGG 和 AAGGG 复合物作为主要产物。这些金属催化的肽寡聚化过程遵循质谱法。报道了五肽复合物 [(C6Me6)Ru(GGGGGOMe-H+)] 的合成和表征。