allyl (2S,3S)-2-(((allyloxy)carbonyl)amino)-3-mercaptobutanoate | 1374893-40-9

• 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: allyl (2S,3S)-2-(((allyloxy)carbonyl)amino)-3-mercaptobutanoate
• CAS: 1374893-40-9
• 化学式: C₁₁H₁₇NO₄S
• 分子量: 259.326
• InChiKey: JFGIXCIQXVBMOL-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  64.63
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (2S,3S)-3-(4-Methoxy-benzylsulfanyl)-2-(4-nitro-benzenesulfonylamino)-butyric acid allyl ester 在 4-甲氧基苯硫酚 、 mercury(II) diacetate 、 potassium carbonate 、 苯甲醚 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 34.0h， 生成 allyl (2S,3S)-2-(((allyloxy)carbonyl)amino)-3-mercaptobutanoate
  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.