trans-4-methyl-L-proline | 23009-50-9

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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
• 英文名称: trans-4-methyl-L-proline
• 英文别名: (2S,4R)-4-methylproline；4-Methyl-proline；(2S,4R)-4-methylpyrrolidin-1-ium-2-carboxylate
• CAS: 23009-50-9
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: KKJQZEWNZXRJFG-UHNVWZDZSA-N

物化性质

• 熔点：
  230-238 °C
• 沸点：
  250.2±33.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-4-methyl-L-proline 在 碳酸氢钠 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 67.0h， 生成 N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester
  参考文献：
  名称：

  Reciprocity of Steric and Stereoelectronic Effects in the Collagen Triple Helix

  摘要：

  In previous work, we demonstrated that 4-fluoroproline residues can contribute greatly to the conformational stability of the collagen triple helix, and that this stability arises from stereoelectronic effects that fix the pucker of the pyrrolidine ring and thereby preorganize the backbone properly for triple-helix formation. Here, we take a reciprocal approach, demonstrating that the steric effect of a 4-methyl group confers stability similar to that from a 4-fluoro group in the opposite configuration. Such fundamental interplay between steric and stereoelectronic effects is heretofore unknown in proteins-natural or synthetic-and provides a new means to modulate conformational stability.

  DOI：

  10.1021/ja061793d
• 作为产物：
  描述：

  L-亮氨酸乙酯 在 sodium hydroxide 、 sodium hypochlorite 、 硫酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 42.83h， 生成 trans-4-methyl-L-proline
  参考文献：
  名称：

  新合成的l-氨基酸-I：脯氨酸，顺式（反式）甲基3（4）l-脯氨酸

  摘要：

  通过在硫酸中辐照N-氯-1-氨基酸3a-d进行的霍夫曼-勒夫勒-弗雷塔格反应产生δ-氯化的化合物，可以将其环化为l-脯氨酸4a-e。这种方便的合成方法不会影响原料的不对称中心，而无需拆分即可直接生成光学纯的脯氨酸。

  DOI：

  10.1016/0040-4020(80)88020-3

文献信息

• Kozupeptins, Antimalarial Agents Produced by <i>Paracamarosporium</i> Species: Isolation, Structural Elucidation, Total Synthesis, and Bioactivity
  作者：Yumi Hayashi、Wataru Fukasawa、Tomoyasu Hirose、Masato Iwatsuki、Rei Hokari、Aki Ishiyama、Masahiro Kanaida、Kenichi Nonaka、Akira Také、Kazuhiko Otoguro、Satoshi O̅mura、Kazuro Shiomi、Toshiaki Sunazuka

  DOI：10.1021/acs.orglett.9b00483

  日期：2019.4.5

  They exhibited potent antimalarial activity against chloroquine-sensitive and -resistant Plasmodium falciparum strains in vitro. The structural elucidation was accomplished by a combination of spectroscopic analyses and chemical approaches including a total synthesis of kozupeptin A. Synthetic kozupeptin A demonstrated a therapeutic effect in vivo, and an intermediate exhibited much higher antimalarial

  Kozupeptins A和B，新型抗疟疾脂肽，是从Paracamarosporium sp。的培养液中分离得到的。FKI-7019。它们在体外对氯喹敏感和耐药的恶性疟原虫菌株表现出有效的抗疟疾活性。结构解析是通过光谱分析和化学方法的结合来完成的，其中包括kozupeptin A的全合成。合成的kozupeptin A在体内显示出治疗效果，并且中间体显示出比kozupeptin A高得多的抗疟活性。
• Energetic contribution to both acidity and conformational stability in peptide models
  作者：Vladimir Kubyshkin、Patrick Durkin、Nediljko Budisa

  DOI：10.1039/c5nj03611a

  日期：——

  The acidity difference of the amide rotamers has been revised for a large set ofN-acetyl amino acids.

  酰胺构象异构体的酸度差异已经针对大量的N-乙酰氨基酸进行了修订。
• SULFONAMIDE-BASED ORGANOCATALYSTS AND METHOD FOR THEIR USE
  申请人：Carter Rich Garrett

  公开号：US20100184986A1

  公开（公告）日：2010-07-22

  Organocatalysts, particularly proline sulfonamide organocatalysts, having a first general formula as follows are disclosed. Embodiments of a method for using these organocatalysts also are disclosed. The method comprises providing a disclosed organocatalyst, and performing a reaction, often an enantioselective or diastereoselective reaction, using the organocatalyst. Solely by way of example, disclosed catalysts can be used to perform aldol reactions, conjugate additions, Michael additions, Robinson annulations, Mannich reactions, α-aminooxylations, α-hydroxyaminations, α-aminations and alkylation reactions. Certain of such reactions are intramolecular cyclizations used to form cyclic compounds, such as 5- or 6-membered rings, having one or more chiral centers. Disclosed organocatalysts generally are much more soluble in typical solvents used for organic synthesis than are known compounds. Moreover, the reaction yield is generally quite good with disclosed compounds, as is their enantioselective and diastereoselective effectiveness.

  披露了具有如下一般公式之一的有机催化剂，尤其是脯氨酸磺酰胺有机催化剂。还披露了使用这些有机催化剂的方法的实施例。该方法包括提供一种披露的有机催化剂，并使用该有机催化剂进行反应，通常是立体选择性的反应或对映选择性反应。仅作为示例，披露的催化剂可用于进行aldol反应、共轭加成、Michael加成、Robinson环化反应、Mannich反应、α-氨基氧化、α-羟基胺化、α-胺化和烷基化反应。其中一些反应是分子内环化反应，用于形成具有一个或多个手性中心的环状化合物，例如5或6元环。披露的有机催化剂通常比已知的化合物更容易溶于用于有机合成的典型溶剂中。此外，使用披露化合物的反应收率通常相当好，它们的对映选择性和非对映选择性效果也很好。
• Isoquinoline compound and pharmaceutical use thereof
  申请人：Mitsubishi Pharma Corporation

  公开号：US20040248931A1

  公开（公告）日：2004-12-09

  The present invention relates to an isoquinoline compound represented by the following formula (I), an optically active form thereof, a pharmaceutically acceptable salt thereof, a water adduct thereof, a hydrate thereof and a solvate thereof, as well as an agent for the prophylaxis and/or treatment of a disease caused by hyperreactivity of poly(ADP-ribose)polymerase, containing the compound, and a poly(ADP-ribose)polymerase inhibitor containing the compound. In addition, this compound is useful as an agent for the prophylaxis and/or treatment of cerebral infarction, particularly as an agent for the prophylaxis and/or treatment of acute cerebral infarction. Furthermore, this compound is useful as a prophylactic and/or therapeutic agent that improves neurological symptoms associated with cerebral infarction, particularly acute cerebral infarction. 1 wherein the symbols are the same as defined in the description.

  本发明涉及一种异喹啉化合物，其由以下通式(I)表示，包括其光学活性形式、药学上可接受的盐、水合物、水合物和溶剂合物，以及用于预防和/或治疗由聚(ADP-核糖)聚合酶过度反应性引起的疾病的药物组合物，包含该化合物，以及包含该化合物的聚(ADP-核糖)聚合酶抑制剂。此外，该化合物可作为预防和/或治疗脑梗塞，特别是急性脑梗塞的药物。此外，该化合物可作为改善与脑梗塞，特别是急性脑梗塞相关的神经症状的预防和/或治疗药物。其中，符号的定义与说明书中的定义相同。
• Remote C–H Hydroxylation by an α-Ketoglutarate-Dependent Dioxygenase Enables Efficient Chemoenzymatic Synthesis of Manzacidin C and Proline Analogs
  作者：Christian R. Zwick、Hans Renata

  DOI：10.1021/jacs.7b12918

  日期：2018.1.24

  demonstrate the practical utility of this transformation in the concise syntheses of a rare alkaloid, manzacidin C, and densely substituted amino acid derivatives with remarkable step efficiency. This work provides a blueprint for future applications of Fe/αKG hydroxylation in complex molecule synthesis and the development of powerful synthetic paradigms centered on enzymatic C-H functionalization logic

  远端位置的选择性 CH 官能化仍然是有机合成中极具挑战性的问题。尽管大自然已经进化出无数能够实现这一壮举的酶，但它们的合成效用在很大程度上被忽视了。在这里，我们在功能上表征了一种α-酮戊二酸依赖性双加氧酶（Fe/αKG），它选择性地羟基化各种脂肪族氨基酸的 δ 位置。与催化类似反应的其他 Fe/αKG 相比，该酶的动力学分析和底物分析显示出优异的催化效率和底物混杂性。我们证明了这种转化在稀有生物碱、manzacin C 和密集取代的氨基酸衍生物的简洁合成中的实际效用，具有显着的步骤效率。