Z-D-谷氨酸-γ-甲酯 | 27025-24-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 谷氨酸类衍生物
• 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: Z-D-谷氨酸-γ-甲酯
• 中文别名: Z-D-谷氨酸5-苄酯；Z-D-谷氨酸 5-苄酯
• 英文名称: Z-D-glutamic γ-methyl ester
• 英文别名: Z-D-Glu(OCH₃)-OH；4-(R)-carboxy-4-(N-benzyloxycarbonylamino)-butanoic acid methyl ester；(R)-2-(((Benzyloxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid；(2R)-5-methoxy-5-oxo-2-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 27025-24-7
• 化学式: C₁₄H₁₇NO₆
• 分子量: 295.292
• InChiKey: JSNVOAWDAFVIKY-LLVKDONJSA-N

物化性质

• 熔点：
  65-70 °C
• 沸点：
  510.6±50.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  Z-D-谷氨酸-γ-甲酯 在 palladium on activated charcoal 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 甲醇 、 氯仿 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成
  参考文献：
  名称：

  Synthesis and Activity of Dipeptides, Linked to Targeting Ligands, as Specific NK Cell Enhancers

  摘要：

  Water soluble analogues of the lipophilic immunostimulant, octadecyl D-alanyl-L-glutamine, BCH-527, were synthesized and evaluated for the ability to stimulate natural killer (NK) cells. One of these compounds in which the octadecyl chain of BCH-527 was replaced with a shorter chain alcohol, 6-(D-alanyl-L-glutaminylamino)hexan-1-ol, 9, displayed an in vitro stimulation of NK cells comparable to that of interleukin 2 (IL 2). However, when the hydroxyl of 9 was linked to L-fucose to yield 1-beta-[6-(D-alanyl-L-glutaminylamino)hex-1-yl]-L-fucopyranose (BCH-2537 1), the observed stimulation of NK cells was greater than that observed with IL 2. Further evaluation of these compounds revealed that the improved in vitro activity of BCH-2537 was more pronounced in vivo. That is, while both compounds significantly increased splenic NK cells, only BCH-2537 significantly increased the activity of these cells in vivo. In terms of a structure-activity relationship, NK cell activity was sensitive to minor structural modifications. It was influenced by conservative substitutions within the dipeptide, the length of the hydrocarbon chain, and the functionality at the end of the chain. No other compound enhanced NK cell activity to the extent exhibited by BCH-2537, although a few were equipotent to 9.

  DOI：

  10.1021/jm970734v
• 作为产物：
  描述：

  D-谷氨酸 在 氯化亚砜 、 碳酸氢钠 作用下， 反应 4.0h， 生成 Z-D-谷氨酸-γ-甲酯
  参考文献：
  名称：

  喹唑啉抗叶酸胸苷酸合酶抑制剂：2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid（ICI 198583）的γ-连接的LD，DD和DL二肽类似物。

  摘要：

  描述了γ-连接的2-脱氨基-2-甲基-N10-炔丙基-5,8-二氮杂萘甲酸的LD，DD和DL二肽类似物的合成（ICI 198583）。合成这些分子的通用方法包括采用溶液相肽合成法制备二肽衍生物，然后通过氰基磷酸二乙酯（DEPC）活化将二肽游离碱与适当的蝶酸类似物缩合。在最后一步中，通过三氟乙酸（TFA）水解除去叔丁酯。ZL-Glu-OBut-γ-D-Ala-OBut例如是由N-（苄氧羰基）-L-谷氨酸的α-叔丁基和D-丙氨酸的叔丁基通过异丁基-混合酸酐偶联制备的。通过催化氢解除去Z-基团，并通过DEPC偶联将所得的二肽游离碱与2-脱氨基-2-甲基-N10-炔丙基-5,8-二脱氮杂戊酸缩合。最后，通过TFA水解除去叔丁酯，得到ICI198583-γ-D-Ala。测试这些化合物作为胸苷酸合酶和L1210细胞生长的抑制剂。发现与γ-连接的LD二肽具有良好的酶和生长抑制活性，最好的例子是Glu-γ-D-Glu衍生物35（Ki

  DOI：

  10.1021/jm950471+

文献信息

• An expedient synthesis of non-racemic N-alkylated pyrrolidin-2,5-diones and piperidin-2,6-diones as peptidomimetics
  作者：Anne Brethon、Claire Bouix-Peter、Laurence Clary、Jean-François Fournier、Craig S. Harris、Claude Lardy、Didier Roche、Vincent Rodeschini、Sandrine Talano

  DOI：10.1016/j.tetlet.2016.11.083

  日期：2016.12

  In our hands, access to 2 novel peptidomimetic scaffolds, based on N-alkylated pyrroldin-2,5-diones and piperidin-2,6-diones, proved to be much more challenging than anticipated. In this short communication, we disclose the strategies that we explored and our final route choices to the desired scaffolds with control of both stereocenters.

  在我们看来，使用2种基于N-烷基吡咯烷2,5-二酮和哌啶2,6-二酮的新型拟肽支架比预期的更具挑战性。在这段简短的交流中，我们将揭示我们探索的策略以及在控制两个立体中心的情况下最终通往所需支架的最终路线选择。
• Polypeptides. Part XIX. The synthesis of some sequential polypeptides of β-methyl aspartate and γ-methyl glutamate
  作者：Akhtar Ali、P. M. Hardy、H. N. Rydon

  DOI：10.1039/p19720001070

  日期：——

  Four sequential polypeptides containing β-methyl aspartyl and γ-methyl glutamyl residues have been prepared by polymerisation of the corresponding oligopeptide N-succinimidyl esters, which were synthesised by conventional methods, using the benzyloxycarbonyl group for N-protection and the t-butyl ester group for carboxy-protection. The polypeptides had molecular weights (Mn) of about 10,000, and very

  通过聚合相应的寡肽N-琥珀酰亚胺酯，已经制备了四个含有β-甲基天冬氨酰和γ-甲基谷氨酰基残基的连续多肽，这些多肽通过常规方法合成，使用苄氧基羰基用于N-保护和叔丁基酯基。用于羧基保护。所述多肽的分子量（M n）为约10,000，并且伴随聚合反应的消旋化非常少（约2％）。
• Characterization of <scp>l</scp>-Theanine Excitatory Actions on Hippocampal Neurons: Toward the Generation of Novel <i>N</i>-Methyl-<scp>d</scp>-aspartate Receptor Modulators Based on Its Backbone
  作者：Fatiha Sebih、Matthieu Rousset、Salima Bellahouel、Marc Rolland、Marie Celeste de Jesus Ferreira、Janique Guiramand、Catherine Cohen-Solal、Gérard Barbanel、Thierry Cens、Mohammed Abouazza、Adrien Tassou、Maud Gratuze、Céline Meusnier、Pierre Charnet、Michel Vignes、Valérie Rolland

  DOI：10.1021/acschemneuro.7b00036

  日期：2017.8.16

  Camellia sinensis. It has received much attention because of its pleiotropic physiological and pharmacological activities leading to health benefits in humans, especially. We describe here a new, easy, efficient, and environmentally friendly chemical synthesis of l-theanine and l-γ-N-propyl-Gln and their corresponding d-isomers. l-Theanine, and its derivatives obtained so far, exhibited partial coagonistic

  l-茶氨酸（或l - γ - N-乙基-谷氨酰胺）是山茶中发现的主要氨基酸。由于其多效性的生理和药理活性特别是对人类健康有益，因此受到了广泛的关注。在这里，我们描述了一个新的，方便，高效和环境友好的化学合成升-theanine和升-γ- ñ丙基谷氨酰胺和它们对应的d异构体。到目前为止，l-茶氨酸及其衍生物在N-甲基-d处表现出部分拮抗作用。-天冬氨酸（NMDA）受体，对培养的海马神经元没有其他谷氨酸受体的激动作用。该活性保留在非洲爪蟾卵母细胞中表达的NMDA受体上。另外，含有1-甲基茶氨酸的NMDA受体的GluN2A和GluN2B均被1-茶氨酸同样地调节。如在培养的海马神经元上所测量的，从1-茶氨酸到d-茶氨酸的立体化学变化以及乙基取代1-和d-茶氨酸的γ- N位置上的丙基部分显着增强了生物学功效。升因此，-茶氨酸结构代表了开发新型NMDA受体调节剂的有趣骨架。
• 一种制备氮杂吲哚类化合物的方法
  申请人：北京桦冠医药科技有限公司

  公开号：CN111349095A

  公开（公告）日：2020-06-30

  本发明提供了一种制备式(I)所示的氮杂吲哚类化合物的方法。本发明以天然氨基酸为起始物料，合成中间体将其与2‑(N‑叔丁氧羰基氨基)‑3‑甲基吡啶在有机碱存在下反应得到中间体在酸性条件下脱去保护基，再关环得到氮杂吲哚类化合物随后将醇活化或者采用Mitsunobu反应，关环得到式(I)。本发明提供的方法以天然氨基酸为起始物料，避免了手性辅助合成、手性拆分或者由酶催化反应引入手性氨基等繁琐工艺，大大降低了成本，适于工业化大生产。
• Synthesis of N-acyl-.GAMMA.-D-glutamyl peptide derivatives containing a C-terminal small fragment of cholecystokinin and their effects on gastric secretion.
  作者：KOJI IUCHI、KEIZO ITO、GORO TSUKAMOTO

  DOI：10.1248/cpb.36.3433

  日期：——

  N-Acyl-γ-D-glutamyl peptide derivatives containing a C-terminal small fragment of cholecystokinin were prepared and their effects on gastric secretion were investigated. PhCO-D-Glu(Phe-NH2)-NPr2 and PhCO-D-Glu(Asp-Phe-NH2)-NPr2 inhibited gastric secretion, while PhCO-D-Glu(Met-Asp-Phe-NH2)-NPr2 and PhCO-D-Glu(Trp-Met-Asp-Phe-NH2)-NPr2 stimulated gastric secretion. The substitution of the acyl function at the N-terminal of PhCO-D-Glu(Phe-NH2)-NPr2 affected the activity. Z-D-Glu(Phe-NH2)-NPr2, 4-chlorobenzoyl-D-Glu-(Phe-NH2)-NPr2 and isonicotinoyl-D-Glu(Phe-NH2)-NPr2 were found to have more potent inhibitory activity against gastric secretion than proglumide (PhCO-DL-Glu-NPr2).

  制备了含有胆囊收缩素 C 端小片段的 N-酰基-γ-D-谷氨酰肽衍生物，并研究了它们对胃液分泌的影响。PhCO-D-Glu(Phe-NH2)-NPr2和PhCO-D-Glu(Asp-Phe-NH2)-NPr2抑制胃液分泌，而PhCO-D-Glu(Met-Asp-Phe-NH2)-NPr2和PhCO-D-Glu(Trp-Met-Asp-Phe-NH2)-NPr2刺激胃液分泌。PhCO-D-Glu(Phe-NH2)-NPr2 N 端酰基功能的替代影响了其活性。研究发现，Z-D-Glu(Phe-NH2)-NPr2、4-氯苯甲酰基-D-Glu-(Phe-NH2)-NPr2 和异烟酰基-D-Glu(Phe-NH2)-NPr2 对胃液分泌的抑制活性比丙谷胺（PhCO-DL-Glu-NPr2）更强。