(S)-alpha-甲基-4-羧基苯甘氨酸

• 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: (S)-alpha-甲基-4-羧基苯甘氨酸
• 英文名称: (S)-alpha-methyl-4-carboxyphenylglycine
• 英文别名: MCPG；(+)-α-methyl-4-carboxyphenylglycine；(S)-α-methyl-4-carboxyphenylglycine；(S)-M4CPG；(2S)-2-azaniumyl-2-(4-carboxyphenyl)propanoate
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: DNCAZYRLRMTVSF-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(4-methyl-2,5-dioxoimidazolidin-4-yl)benzonitrile 在 盐酸 、 三乙胺 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 401.5h， 生成 (S)-alpha-甲基-4-羧基苯甘氨酸
  参考文献：
  名称：

  Resolution and regioselective protection of glutamic acid analogues. II- Synthesis, resolution and configuration assigsment of (+)-α-methyl-4-car☐yphenylglycine (M4CPG)

  摘要：

  Diastereomeric dipeptides (S)-Leu-(S)-M4CPG and (S)-Leu-(R)-M4CPG have been synthesized from (+/-)-M4CPG and separated by anion exchange chromatography. Absolute configuration of (S)-(+)-M4CPG was assigned by X-Ray crystallography of (S)-Leu-(S)-M4CPG. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00387-4

文献信息

• Asymmetric α-arylation of amino acids
  作者：Daniel J. Leonard、John W. Ward、Jonathan Clayden

  DOI：10.1038/s41586-018-0553-9

  日期：2018.10

  α-aryl amino acids and their derivatives are valuable precursors to bioactive molecules10,11. Here we describe the synthesis of quaternary α-aryl amino acids from enantiopure amino acid precursors by α-arylation without loss of stereochemical integrity. Our approach relies on the temporary formation of a second stereogenic centre in an N′-arylurea adduct12 of an imidazolidinone derivative6 of the precursor

  季氨基酸，其中带有氨基和羧基的 α-碳也带有两个碳取代基，作为肽构象和生物活性的修饰剂以及作为药用重要化合物的前体具有重要作用 1,2。与在该 α-碳上的对映选择性烷基化（有多种方法 3-8）相比，在 α-碳上一般对映选择性引入芳基取代基在合成上具有挑战性 9。尽管如此，由此产生的 α-芳基氨基酸及其衍生物是生物活性分子 10,11 的有价值的前体。在这里，我们描述了通过 α-芳基化从对映纯氨基酸前体合成季 α-芳基氨基酸而不损失立体化学完整性。我们的方法依赖于在前体氨基酸的咪唑啉酮衍生物 6 的 N'-芳基脲加合物中临时形成第二个立体中心，并使用容易获得的对映体纯氨基酸作为前体和不对称的来源。它避免使用有价值的过渡金属，并能够用富电子、贫电子和杂环取代基进行芳基化。产物的任一对映异构体都可由单一氨基酸前体形成。该方法实用且可扩展，并提供了生产数克数量的 α-芳基化季铵氨基酸的机会。该方法
• Stereoselective synthesis of (S )-MPPG, (S)-MTPG and (S )-(+)-αM4CPG from (R)-4-hydroxyphenylglycine
  作者：Dawei Ma、Hongqi Tian

  DOI：10.1039/a704704e

  日期：——

  (R)-4-Hydroxyphenylglycine was protected with a benzyl group and a methyl group was introduced at the α position by using the self-regeneration-of-stereocentre method. After the 4-hydroxy group had been converted into the corresponding trifluoromethanesulfonate (triflate), three palladium-catalyzed reactions were employed to furnish (S)-α-methyl-4-phosphonophenylglycine [(S)-MPPG], (S)-α-methyl-4-(tetrazol-5-yl)phenylglycine [(S)-MTPG] and (S)-4-carboxyphenyl-α-methylglycine [(S)-αM4CPG], a class of new and selective antagonists of metabotropic glutamate receptors.

  (R)-4-羟基苯甘氨酸采用苄基保护，并通过立体中心自再生法在δ位引入一个甲基。在 4-羟基转化为相应的三氟甲磺酸盐（三氟酸盐）后，通过三个钯催化反应生成了(S)-δ-甲基-4-膦酰基苯甘氨酸[(S)-MPG]、(S)-δ-甲基-4-(四唑-5-基)苯基甘氨酸[(S)-MTPG]和(S)-4-羧基苯基-δ-甲基甘氨酸[(S)-δM4CPG]，这是一类新型的选择性代谢谷氨酸受体拮抗剂。
• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Kõster Hubert

  公开号：US20100248264A1

  公开（公告）日：2010-09-30

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Automated systems for performing the methods also are provided.

  提供了捕获化合物及其集合以及使用这些化合物进行生物分子分析的方法。特别地，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂的蛋白质混合物。还提供了执行这些方法的自动化系统。
• Stereoselective synthesis of (S)-(+)-αM4CPG, a selective antagonist of metabotropic glutamate receptors
  作者：Dawei Ma、Hongqi Tian

  DOI：10.1016/0957-4166(96)00182-6

  日期：1996.6
• An efficient access to the enantiomers of α-methyl-4-carboxyphenylglycine via a hydantoin route using a practical variant of preferential crysallization AS3PC (Auto Seeded Programmed Polythermic Preferential Crystallization)11
  作者：E. Ndzié、P. Cardinael、A.-R. Schoofs、G. Coquerel

  DOI：10.1016/s0957-4166(97)00349-2

  日期：1997.9

  The enantiomers are obtained in preparative amounts without a resolving agent via the following sequence: hydantoin synthesis, resolution by entrainment, and ring cleavage by means of hydrolysis in basic conditions. The new variant of preferential crystallization (AS3PC), implemented without using seeds, shows good reproducibility and yield. (C) 1997 Elsevier Science Ltd.