Ac(CSSLF) | 321862-05-9

• 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: Ac(CSSLF)
• 英文别名: Ac-Cys(1)-Ser-Ser-Leu-Phe-(1)；N-[(3S,6S,9S,12S,15R)-3-benzyl-9,12-bis(hydroxymethyl)-6-(2-methylpropyl)-2,5,8,11,14-pentaoxo-1-thia-4,7,10,13-tetrazacyclohexadec-15-yl]acetamide
• CAS: 321862-05-9
• 化学式: C₂₆H₃₇N₅O₈S
• 分子量: 579.674
• InChiKey: NITORXWTOQDAKV-SXYSDOLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  228
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 盐酸胍 、 乙腈 作用下， 以 phosphate buffer 为溶剂， 生成 Ac(CSSLF)
  参考文献：
  名称：

  Cyclic Peptide Inhibitors of Staphylococcal Virulence Prepared by Fmoc-Based Thiolactone Peptide Synthesis

  摘要：

  Virulence factor production in Staphylococcus aureus is largely under the control of the accessory gene regulator (ago quorum sensing system. There are four agr groups, all of which exhibit bacterial interference: each agr type synthesizes a cyclic autoinducing peptide (AIP) with a distinct sequence that activates its cognate AgrC receptor and inhibits activation of others. To better understand inhibitory AIP-AgrC interactions, we aimed to identify the minimal molecular determinants required to inhibit both non-cognate and cognate receptors. This minimization of the AIP pharmacophore also may have therapeutic relevance as the use of native AIPs to block virulence of non-cognate agr strains can prevent the establishment of an infection in vivo. We synthesized and evaluated the inhibitory activities of 10 AIP derivatives based on a truncated AIP analogue that inhibits all four agr types. To carry out the rapid, parallel synthesis of these peptides, we employed a new linker for Fmoc-based thioester peptide synthesis. Our results identify key structural elements that are necessary for AgrC inhibition and reveal key differences between non-cognate and cognate inhibitory requirements.

  DOI：

  10.1021/ja711126e

文献信息

• Simplified Structural Mimetics of AIPS as Quorum Sensing Inhibitors
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20180170889A1

  公开（公告）日：2018-06-21

  Compounds that regulate quorum sensing in Staphylococcal bacteria and in particular in Staphylococcus aureus are provided. Compounds are described in formulas I, II, III, IV, V and VI herein. One or more compounds herein can be employed to inhibit QS and to thus inhibit virulence in Staphylococcus bacteria and in particular in Staphylococcus aureus. Compounds herein and pharmaceutical compositions containing one or more of these compounds are useful, for example, in treating infections of Staphylococcus bacteria and in particular of Staphylococcus aureus. Methods for treating such bacterial infections are provided.

  本文提供了调节葡萄球菌细菌中群体感应的化合物，特别是金黄色葡萄球菌中的化合物，其中包括公式I、II、III、IV、V和VI中描述的化合物。其中一个或多个化合物可用于抑制群体感应，从而抑制金黄色葡萄球菌细菌中的毒力。本文中的化合物及含有这些化合物中的一个或多个的药物组合物，例如用于治疗葡萄球菌细菌感染，特别是金黄色葡萄球菌感染，提供了治疗此类细菌感染的方法。