(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((2S,3S)-4-(allyloxy)-3-(allyloxycarbonylamino)-4-oxobutan-2-ylthio)propanoic acid | 1330632-53-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((2S,3S)-4-(allyloxy)-3-(allyloxycarbonylamino)-4-oxobutan-2-ylthio)propanoic acid
• 英文别名: Fmoc-Alloc/Allyl-MeLan；Fmoc-Alloc/Allyl-MeLan-OH
• CAS: 1330632-53-5
• 化学式: C₂₉H₃₂N₂O₈S
• 分子量: 568.648
• InChiKey: GFFCBPXZZIDZJS-RIEVBORMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  40.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  140.26
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((2S,3S)-4-(allyloxy)-3-(allyloxycarbonylamino)-4-oxobutan-2-ylthio)propanoic acid 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  羊毛硫抗生素乳酸菌素 3147 两种成分的固体负载化学合成

  摘要：

  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。

  DOI：

  10.1021/ja206017p
• 作为产物：
  描述：

  allyl (2S,3S)-2-(((allyloxy)carbonyl)amino)-3-mercaptobutanoate 在 苯硅烷 、 四丁基溴化铵 、 碳酸氢钠 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((2S,3S)-4-(allyloxy)-3-(allyloxycarbonylamino)-4-oxobutan-2-ylthio)propanoic acid
  参考文献：
  名称：

  Chemical Synthesis and Biological Activity of Analogues of the Lantibiotic Epilancin 15X

  摘要：

  Lantibiotics are a large family of antibacterial peptide natural products containing multiple post-translational modifications, including the thioether structures lanthionine and methyllanthionine. Efforts to probe structure activity relationships and engineer improved pharmacological properties have driven the development of new methods to produce non-natural analogues of these compounds. In this study, solid-supported chemical synthesis was used to produce analogues of the potent lantibiotic epilancin 15X, in order to assess the importance of several N-terminal post-translational modifications for biological activity. Surprisingly, substitution of these moieties, including the unusual N-terminal D-lactyl moiety, resulted in relatively small changes in the antimicrobial activity and pore-forming ability of the peptides.

  DOI：

  10.1021/ja302435y

文献信息

• Ring-opening reactions for the solid-phase synthesis of nisin lipopeptide analogues
  作者：Daniel B. Engelhardt、Bethan L. Donnelly、Jonathan Beadle、Marco J. van Belkum、John C. Vederas

  DOI：10.1039/d2ob01526a

  日期：——

  Three lipopeptide analogues of the lantibiotic nisin A have been synthesised on-resin using Fmoc-SPPS techniques to investigate the structure–activity relationship of the A and B ring of these types of lanthipeptides. Lanthionine and methyllanthionine macrocycles were incorporated using orthogonally protected residues for on-resin cyclisation. Unsaturated dehydroalanine and, for the first time, dehydrobutyrine

  已经使用 Fmoc-SPPS 技术在树脂上合成了羊毛硫抗生素乳链菌肽 A 的三种脂肽类似物，以研究这些类型的羊毛硫肽的 A 环和 B 环的结构-活性关系。羊毛硫氨酸和甲基羊毛硫氨酸大环化合物使用正交保护的残基用于树脂上环化。不饱和脱氢丙氨酸和脱氢丁酸首次从其半胱氨酸衍生物在树脂上合成。然而，乳链菌肽的合成或半合成脂肽类似物均未显示出对通常对乳链菌肽敏感的细菌菌株的抑制活性。
• Synthesis and Bioactivity of Diastereomers of the Virulence Lanthipeptide Cytolysin
  作者：Subha Mukherjee、Liujie Huo、Gabrielle N. Thibodeaux、Wilfred A. van der Donk

  DOI：10.1021/acs.orglett.6b03246

  日期：2016.12.2

  Cytolysin, a two-component lanthipeptide comprising cytolysin S (CylL(s)") and cytolysin L (CyILL"), is the only family member to exhibit lytic activity against mammalian cells in addition to synergistic antimicrobial activity. A subset of the thioether cross-links of CylLs" and CylL(L)," have LL stereochemistry instead of the canonical DL stereochemistry in all previously characterized lanthipeptides. The synthesis of a CylLs" variant with DL stereochemistry is reported. Its antimicrobial activity was found to be decreased, but not its lytic activity against red blood cells. Hence, the unusual LL stereochemistry is not responsible for the lytic activity.