Boc-L-alanyl-D-glutamic acid diethyl ester | 1386397-92-7

• 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: Boc-L-alanyl-D-glutamic acid diethyl ester
• 英文别名: diethyl (tert-butoxycarbonyl)-L-alanyl-D-glutamate；diethyl (2R)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]pentanedioate
• CAS: 1386397-92-7
• 化学式: C₁₇H₃₀N₂O₇
• 分子量: 374.434
• InChiKey: GIEBXKQLIJMWAK-NWDGAFQWSA-N

物化性质

• 沸点：
  515.3±45.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  120.03
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Boc-L-alanyl-D-glutamic acid diethyl ester 在 盐酸 、 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 为溶剂， 生成 diethyl (1-(tert-butoxycarbonyl)indoline-2-carbonyl)glycyl-L-alanyl-D-glutamate
  参考文献：
  名称：

  Gobec, Martina; Mlinarič-Raščan, Irena; Dolenc, Marija Sollner, European Journal of Medicinal Chemistry, 2016, vol. 116, p. 1 - 12

  摘要：

  DOI：
• 作为产物：
  描述：

  N-Boc-D-Glu(OEt)OEt 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 Boc-L-alanyl-D-glutamic acid diethyl ester
  参考文献：
  名称：

  Gobec, Martina; Mlinarič-Raščan, Irena; Dolenc, Marija Sollner, European Journal of Medicinal Chemistry, 2016, vol. 116, p. 1 - 12

  摘要：

  DOI：

文献信息

• The design and synthesis of Ala-Glu/iGln mimetics: heterocyclic building blocks for pseudopeptides
  作者：Žiga Jakopin

  DOI：10.1016/j.tetlet.2014.12.035

  日期：2015.1

  Heterocyclic Ala-Glu/i-Gln mimetics, in which one or both carboxylic acid functionalities are bioisosterically replaced by a 1,2,4-oxadiazole ring system, are designed and synthesized. A straightforward route for preparing orthogonally protected 1,2,4-oxadiazole-bearing dipeptide building blocks is presented. These compounds constitute a new series of non-natural dipeptides, capable of being integrated

  设计并合成了杂环Ala-Glu / i-Gln模拟物，其中一个或两个羧酸官能团被1,2,4-恶二唑环系统生物等排取代。提出了制备正交保护的带有1,2,4-恶二唑的二肽结构单元的直接方法。这些化合物构成了一系列新的非天然二肽，能够整合到生物学上相关的肽中。合成从d-谷氨酸开始，并且选择温和的反应条件以允许形成产物。
• [EN] CONJUGATED TLR7 AND NOD2 AGONISTS<br/>[FR] AGONISTES CONJUGUÉS DE TLR7 ET DE NOD2
  申请人：UNIV LJUBLJANI

  公开号：WO2022084417A1

  公开（公告）日：2022-04-28

  This invention provides covalent conjugates of TLR7 and NOD2 agonists, processes for preparing such compounds and the use of such compounds in medicine.

  这项发明提供了TLR7和NOD2激动剂的共价结合物，制备这种化合物的方法以及在医学中使用这种化合物的用途。
• A closer look at ligand specificity for cellular activation of NOD2 with synthetic muramyl dipeptide analogues
  作者：Christopher Adamson、Yaquan Liang、Shiliu Feng、Allan Wee Ren Ng、Yuan Qiao

  DOI：10.1039/d3cc05807g

  日期：——

  To further understand the specificity of muramyl dipeptide (MDP) sensing by NOD2, we evaluated the compatibility of synthetic MDP analogues for cellular uptake and NAGK phosphorylation, the pre-requisite steps of intracellular NOD2 activation.

  为了进一步了解 NOD2 对氨甲酰二肽（MDP）感应的特异性，我们评估了合成 MDP 类似物对细胞摄取和 NAGK 磷酸化的兼容性，这是细胞内 NOD2 激活的前提步骤。
• Immunomodulatory Properties of Novel Nucleotide Oligomerization Domain 2 (Nod2) Agonistic Desmuramyldipeptides
  作者：Žiga Jakopin、Martina Gobec、Irena Mlinarič-Raščan、Marija Sollner Dolenc

  DOI：10.1021/jm300503b

  日期：2012.7.26

  There is a pressing need for the development of novel adjuvants for human use. The minimal bioactive structure of bacterial peptidoglycan (PGN), muramyldipeptide (MDP), and its derivative murabutide (MB) have long been known for their adjuvant activities. For this reason, a series of novel desmuramyldipepticles have been designed and synthesized as part of our search for therapeutically useful MDP analogues. Since nucleotide oligomerization domain 2 (Nod2) is a putative receptor for MDP, we used engineered HEK293 cells overexpressing Nod2 to screen and validate our compounds for their Nod2-agonist activity. Their immunomodulatory properties were subsequently assessed in vitro by evaluating their effect on proinflammatory cytolcine production of phorbol 12-myristate 13-acetate (PMA)/ionomycin-stimulated human peripheral blood mononuclear cells (PBMCs). Herein, we present novel desmuramyldipeptides, the most active of them possessing immunoenhancing properties as a result of their potent Nod2-agonistic effect.