(2S,6R)-羊毛硫氨酸 | 922-56-5

• 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: (2S,6R)-羊毛硫氨酸
• 英文名称: meso-lanthionine
• 英文别名: (R)-2-amino-3-((S)-2-amino-2-carboxyethylthio)propanoic acid；meso-Lanthionin；lanthionine；meso-2,2'-diamino-3,3-sulfanediyl-bis-propionic acid；meso-Bis-(2-amino-2-carboxy-aethyl)-sulfid；(R:S)-Bis-(2-amino-2-carboxy-aethyl)-sulfid；(R)-S-(2-amino-2-carboxyethyl)-D-cysteine；(2S)-2-azaniumyl-3-[(2R)-2-azaniumyl-2-carboxylatoethyl]sulfanylpropanoate
• CAS: 922-56-5
• 化学式: C₆H₁₂N₂O₄S
• 分子量: 208.238
• InChiKey: DWPCPZJAHOETAG-ZXZARUISSA-N

物化性质

• 熔点：
  283℃ (decomposition)
• 沸点：
  462.6±45.0 °C(Predicted)
• 密度：
  1.499±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  (2S,6R)-羊毛硫氨酸 在 盐酸 、 水 、 双氧水 作用下， 生成 meso-lanthionine-S-oxide
  参考文献：
  名称：

  Zahn; Osterloh, Justus Liebigs Annalen der Chemie, 1955, vol. 595, p. 237,240

  摘要：

  DOI：
• 作为产物：
  描述：

  L-半胱氨酸 在 2-乙酰氨基丙烯酸 作用下， 生成 (2S,6R)-羊毛硫氨酸 、 L-羊毛硫氨酸
  参考文献：
  名称：

  Schoeberl, Chemische Berichte, 1947, vol. 80, p. 381,384

  摘要：

  DOI：

文献信息

• Solid Supported Chemical Syntheses of Both Components of the Lantibiotic Lacticin 3147
  作者：Wei Liu、Alice S. H. Chan、Hongqiang Liu、Stephen A. Cochrane、John C. Vederas

  DOI：10.1021/ja206017p

  日期：2011.9.14

  peptides produced by bacteria. Some are employed for food preservation, whereas others have therapeutic potential due to their activity against organisms resistant to current antibiotics. They are ribosomally synthesized and posttranslationally modified by dehydration of serine and threonine residues followed by attack of thiols of cysteines to form monosulfide lanthionine and methyllanthionine rings

  羊毛硫抗生素是细菌产生的抗菌肽。一些用于食品保存，而另一些则具有治疗潜力，因为它们对当前抗生素耐药的生物体具有活性。它们是核糖体合成的，并通过丝氨酸和苏氨酸残基脱水，然后攻击半胱氨酸的硫醇，分别形成单硫化羊毛硫氨酸和甲基羊毛硫氨酸环进行翻译后修饰。肽类似物的化学合成是验证立体化学和获取构效关系的有力方法。然而，由于生成具有正交保护和良好立体化学控制的羊毛硫氨酸和甲基羊毛硫氨酸的问题，羊毛硫抗生素的固体支持合成一直很困难。
• High-temperature oxidation of CoGa: Influence of the crystallographic orientation on the oxidation rate
  作者：U. Koops、D. Hesse、M. Martin

  DOI：10.1557/jmr.2002.0363

  日期：2002.10

  The crystallographic orientation plays an important role in high-temperature oxidation of the intermetallic compound CoGa. When CoGa is exposed to air at elevated temperatures, the oxide β–Ga₂O₃is formed, and different scale growth rates are observed, depending on the crystallographic orientation of the CoGa grains. This dependence is a consequence of the anisotropy of the gallium diffusion rate through the β–Ga₂O₃scale and of a topotaxial orientation relationship occurring between β–Ga₂O₃and CoGa. The combination ofex situtechniques, such as transmission electron microscopy and electron backscatter diffraction with optical microscopy, appliedin situresulted in a thorough understanding of these relations and of the oxidation process in general.

  晶体取向在金属间化合物 CoGa 的高温氧化过程中起着重要作用。当 CoGa 在高温下暴露于空气中时，会形成氧化物 β-Ga2O3，根据 CoGa 晶粒的晶体学取向，会观察到不同的鳞片生长率。这种依赖性是镓在β-Ga2O3鳞片中的扩散速率各向异性以及β-Ga2O3和CoGa之间的拓扑取向关系的结果。将透射电子显微镜、电子反向散射衍射和光学显微镜等实验技术结合在一起，对这些关系和整个氧化过程有了透彻的了解。
• Stereoselective synthesis of lanthionine derivatives in aqueous solution and their incorporation into the peptidoglycan of Escherichia coli
  作者：Thibaut Denoël、Astrid Zervosen、Thomas Gerards、Christian Lemaire、Bernard Joris、Didier Blanot、André Luxen

  DOI：10.1016/j.bmc.2014.07.023

  日期：2014.9

  The three diastereoisomers-(R,R), (S,S) and meso-of lanthionine were synthesized in aqueous solution with high diastereoselectivity (>99%). The (S) and (R) enantiomers of two differently protected sulfamidates were opened by nucleophilic attack of (R) or (S)-cysteine. Acidification and controlled heating liberated the free lanthionines. Using the same chemistry, an α-benzyl lanthionine was also prepared. The proposed method, which avoids the need of enrichment by recrystallization, opens the way to the labelling of these compounds with (35)S. Furthermore, in vivo bioincorporation into Escherichia coli W7 was studied. No incorporation of α-benzyl lanthionine was observed. In contrast, meso-lanthionine can effectively replace meso-diaminopimelic acid in vivo, while in the presence of (R,R)-lanthionine the initial increase of bacterial growth was followed by cell lysis. In the future, meso-[(35)S]lanthionine could be used to study the biosynthesis of peptidoglycan and its turnover in relation to cell growth and division.
• Schoeberl, Chemische Berichte, 1943, vol. 76, p. 964,967
  作者：Schoeberl

  DOI：——

  日期：——
• 82. Syntheses of some polymeric polypeptides of lanthionine
  作者：Max Frankel、David Gertner

  DOI：10.1039/jr9610000459

  日期：——