(R)-2-methylcysteic acid | 1127229-09-7

• 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: (R)-2-methylcysteic acid
• 英文别名: 2-methylcysteic acid；(2R)-2-amino-2-methyl-3-sulfopropanoic acid
• CAS: 1127229-09-7
• 化学式: C₄H₉NO₅S
• 分子量: 183.185
• InChiKey: YMYOFTPCKHNXPA-BYPYZUCNSA-N

物化性质

• 密度：
  1.643±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-2-methylcysteic acid 、 NAlpha-(5-氟-2,4-二硝基苯基)-L-亮氨酰胺 在 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Cyclic Depsipeptides, Grassypeptolides D and E and Ibu-epidemethoxylyngbyastatin 3, from a Red Sea Leptolyngbya Cyanobacterium

  摘要：

  Two new grassypeptolides and a lyngbyastatin analogue, together with the known dolastatin 12, have been isolated from field collections and laboratory cultures of the marine cyanobacterium Leptolyngbya sp. collected from the SS Thistlegorm shipwreck in the Red Sea. The overall stereostructures of grassypeptolides D (1) and E (2) and Ibu-epidemethoxylyngbyastatin 3 (3) were determined by a combination of 1D and 2D NMR experiments, MS analysis, Marfey's methodology, and HPLC-MS. Compounds 1 and 2 contain 2-methyl-3-aminobutyric acid and 2-aminobutyric acid, while biosynthetically distinct 3 contains 3-amino-2-methylhexanoic acid and the beta-keto amino acid 4-amino-2,2-dimethyl-3-oxopentanoic acid (Ibu). Grassypeptolides D (1) and E (2) showed significant cytotoxicity to HeLa (IC50 = 335 and 192 nM, respectively) and mouse neuro-2a blastoma cells (IC50 = 599 and 407 nM, respectively), in contrast to Ibu-epidemethoxylyngbyastatin 3 (neuro-2a cells, IC50 > 10 mu M) and dolastatin 12 (neuro-2a cells, IC50 > 1 mu M).

  DOI：

  10.1021/np200270d
• 作为产物：
  描述：

  2-甲基-L-半胱氨酸盐酸盐 在 甲酸 、 双氧水 作用下， 反应 1.0h， 生成 (R)-2-methylcysteic acid
  参考文献：
  名称：

  Kinenzoline 的分离和全合成，一种从海洋 Salileptolyngbya sp. 中分离的抗锥虫线性缩肽。蓝藻

  摘要：

  Kinenzoline ( 1 ) 是一种新的线性缩酚肽，是从海洋Salileptolyngbya sp. 中分离出来的。蓝藻。通过光谱分析和降解反应阐明了其结构。此外，我们实现了1的全合成并确认了其结构。与正常人类细胞 (WI-38, IC 50 > 100 μM)相比，Kinenzoline ( 1 ) 对昏睡病的病原体罗得西锥虫(IC 50 4.5 μM ) 显示出高度选择性的抗增殖活性。Kinenzoline ( 1 ) 是一种很有前景的先导化合物，可用于开发新的抗锥虫病药物。

  DOI：

  10.1021/acs.joc.1c00817

文献信息

• [EN] METHODS OF PREPARATION OF MACROCYCLIC COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS MACROCYCLIQUES
  申请人：UNIV FLORIDA

  公开号：WO2009105284A1

  公开（公告）日：2009-08-27

  The instant invention describes methods for producing macrocyclic compounds having antiproliferation activity, and useful in methods of treating disorders such as cancer, tumors and cell proliferation related disorders.

  这项即时发明描述了生产具有抗增殖活性的大环化合物的方法，这些化合物在治疗癌症、肿瘤和与细胞增殖有关的疾病的方法中非常有用。
• The Hoiamides, Structurally Intriguing Neurotoxic Lipopeptides from Papua New Guinea Marine Cyanobacteria
  作者：Hyukjae Choi、Alban R. Pereira、Zhengyu Cao、Cynthia F. Shuman、Niclas Engene、Tara Byrum、Teatulohi Matainaho、Thomas F. Murray、Alfonso Mangoni、William H. Gerwick

  DOI：10.1021/np100468n

  日期：2010.8.27

  Two related peptide metabolites, one a cyclic depsipeptide, hoiamide B (2), and the other a linear lipopeptide, hoiamide C (3), were isolated from two different collections of marine cyanobacteria obtained in Papua New Guinea. Their structures were elucidated by combining various techniques in spectroscopy, chromatography, and synthetic chemistry. Both metabolites belong to the unique hoiamide structural

  从巴布亚新几内亚获得的两个不同的海洋蓝细菌集合中分离出两种相关的肽代谢物，一种是环状缩酚肽，hoiamide B ( 2 )，另一种是线性脂肽，hoiamide C ( 3 )。通过结合光谱学、色谱法和合成化学的各种技术，阐明了它们的结构。两种代谢物都属于独特的 hoiamide 结构类别，其特征是具有乙酸盐延伸和S-腺苷甲硫氨酸修饰的异亮氨酸单元、由两个 α-甲基化噻唑啉和一个噻唑组成的中心三杂环系统，以及高度氧化和甲基化的 C-15 聚酮化合物单元。在新皮质神经元中，环缩肽2刺激钠流入并抑制自发 Ca 2+振荡，EC 50值分别为 3.9 μM 和 79.8 nM，而3在这些测定中没有显着影响。
• Isolation and Total Synthesis of Kinenzoline, an Antitrypanosomal Linear Depsipeptide Isolated from a Marine <i>Salileptolyngbya</i> sp. Cyanobacterium
  作者：Naoaki Kurisawa、Keisuke Otomo、Arihiro Iwasaki、Ghulam Jeelani、Tomoyoshi Nozaki、Kiyotake Suenaga

  DOI：10.1021/acs.joc.1c00817

  日期：2021.9.17

  Kinenzoline (1), a new linear depsipeptide, was isolated from a marine Salileptolyngbya sp. cyanobacterium. Its structure was elucidated by spectroscopic analyses and degradation reactions. In addition, we achieved a total synthesis of 1 and confirmed its structure. Kinenzoline (1) showed highly selective antiproliferative activity against the causative organism of sleeping sickness, Trypanosoma brucei

  Kinenzoline ( 1 ) 是一种新的线性缩酚肽，是从海洋Salileptolyngbya sp. 中分离出来的。蓝藻。通过光谱分析和降解反应阐明了其结构。此外，我们实现了1的全合成并确认了其结构。与正常人类细胞 (WI-38, IC 50 > 100 μM)相比，Kinenzoline ( 1 ) 对昏睡病的病原体罗得西锥虫(IC 50 4.5 μM ) 显示出高度选择性的抗增殖活性。Kinenzoline ( 1 ) 是一种很有前景的先导化合物，可用于开发新的抗锥虫病药物。
• Cyclic Depsipeptides, Grassypeptolides D and E and Ibu-epidemethoxylyngbyastatin 3, from a Red Sea <i>Leptolyngbya</i> Cyanobacterium
  作者：Christopher C. Thornburg、Muralidhara Thimmaiah、Lamiaa A. Shaala、Andrew M. Hau、Jay M. Malmo、Jane E. Ishmael、Diaa T. A. Youssef、Kerry L. McPhail

  DOI：10.1021/np200270d

  日期：2011.8.26

  Two new grassypeptolides and a lyngbyastatin analogue, together with the known dolastatin 12, have been isolated from field collections and laboratory cultures of the marine cyanobacterium Leptolyngbya sp. collected from the SS Thistlegorm shipwreck in the Red Sea. The overall stereostructures of grassypeptolides D (1) and E (2) and Ibu-epidemethoxylyngbyastatin 3 (3) were determined by a combination of 1D and 2D NMR experiments, MS analysis, Marfey's methodology, and HPLC-MS. Compounds 1 and 2 contain 2-methyl-3-aminobutyric acid and 2-aminobutyric acid, while biosynthetically distinct 3 contains 3-amino-2-methylhexanoic acid and the beta-keto amino acid 4-amino-2,2-dimethyl-3-oxopentanoic acid (Ibu). Grassypeptolides D (1) and E (2) showed significant cytotoxicity to HeLa (IC50 = 335 and 192 nM, respectively) and mouse neuro-2a blastoma cells (IC50 = 599 and 407 nM, respectively), in contrast to Ibu-epidemethoxylyngbyastatin 3 (neuro-2a cells, IC50 > 10 mu M) and dolastatin 12 (neuro-2a cells, IC50 > 1 mu M).