pericosine Do | 1275591-55-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pericosine Do
• 英文别名: methyl (3R,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate；(-)-Pericosine Do；methyl (3R,4S,5S,6S)-6-chloro-3,4,5-trihydroxycyclohexene-1-carboxylate
• CAS: 1275591-55-3
• 化学式: C₈H₁₁ClO₅
• 分子量: 222.625
• InChiKey: AEDMWQPFIPNFCS-JRTVQGFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl shikimate 在 吡啶 、 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 oxone 、 camphor-10-sulfonic acid 、 cesium acetate 、 碳酸氢钠 、 乙酰氯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 pericosine Do
  参考文献：
  名称：

  An Electrophilic Natural Product Provides a Safe and Robust Odor Neutralization Approach To Counteract Malodorous Organosulfur Metabolites Encountered in Skunk Spray

  摘要：

  The anal secretions of skunks comprise several types of malodorous organosulfur compounds. The pungent metabolites are used defensively by skunks to repel threats posed by predators, and in many parts of the world, those perceived threats include humans and their pets. The extremely low thresholds for detection of the organosulfur metabolites make efforts to "de-skunk" people, animals, and clothing a process fraught with many challenges. The fungal-derived metabolite pericosine A (4) is a promiscuous yet stabile electrophilic compound that we propose is used by some fungi as a novel form of chemical defense. Our investigations have indicated that pericosine A readily reacts with skunk-spray secretions to transform them into odorless products. Mechanistic and computational studies suggested that pericosine A and its synthetic analogues react via S_N2'-type mechanisms with thiols and thioacetates under aqueous conditions to generate stable thioethers. Testing revealed that pericosine A did not cause skin or eye irritation and was highly effective at deodorizing skunk anal gland secretions when formulated to include adjunctive cosmetic ingredients.

  DOI：

  10.1021/acs.jnatprod.9b00415

文献信息

• Stereostructure Reassignment and Determination of the Absolute Configuration of Pericosine D_o by a Synthetic Approach
  作者：Yoshihide Usami、Koji Mizuki

  DOI：10.1021/np100843j

  日期：2011.4.25

  reassign the structure of pericosine Do (8), a cytotoxic marine natural product produced by the fungus Periconia byssoides OUPS-N133 that was originally derived from the sea hare Aplysia kurodai. Chemical synthesis was used to prepare pericoisne Do (8) from a known chlorohydrin that was in turn derived from (−)-quinic acid. The absolute configuration of natural pericosine Do (8) was determined to be

  化学合成和NMR方法的组合被用来重新分配percosine D o（8）的结构，percosine D o（8）是一种由真菌Periconia byssoides OUPS-N133产生的具有细胞毒性的海洋天然产物，最初源自海兔Aplysia kurodai。化学合成被用来从已知的氯醇制备pericoisne D o（8），而后者又衍生自（-）-奎宁酸。天然pericosine d的绝对构型Ô（8测定）为甲基（3- [R，4小号，5小号，6小号）-6-氯-3,4,5-三羟基-1-环己烯-1-羧酸酯。HPLC分析使用手性相柱表明pericosine d Ô（8）存在于自然界中的对映体纯的形式。
• An Electrophilic Natural Product Provides a Safe and Robust Odor Neutralization Approach To Counteract Malodorous Organosulfur Metabolites Encountered in Skunk Spray
  作者：Lin Du、Charissa Munteanu、Jarrod B. King、Doug E. Frantz、Robert H. Cichewicz

  DOI：10.1021/acs.jnatprod.9b00415

  日期：2019.7.26

  The anal secretions of skunks comprise several types of malodorous organosulfur compounds. The pungent metabolites are used defensively by skunks to repel threats posed by predators, and in many parts of the world, those perceived threats include humans and their pets. The extremely low thresholds for detection of the organosulfur metabolites make efforts to "de-skunk" people, animals, and clothing a process fraught with many challenges. The fungal-derived metabolite pericosine A (4) is a promiscuous yet stabile electrophilic compound that we propose is used by some fungi as a novel form of chemical defense. Our investigations have indicated that pericosine A readily reacts with skunk-spray secretions to transform them into odorless products. Mechanistic and computational studies suggested that pericosine A and its synthetic analogues react via S_N2'-type mechanisms with thiols and thioacetates under aqueous conditions to generate stable thioethers. Testing revealed that pericosine A did not cause skin or eye irritation and was highly effective at deodorizing skunk anal gland secretions when formulated to include adjunctive cosmetic ingredients.