des-thiomethyllooekeyolide A

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: des-thiomethyllooekeyolide A
• 化学式: C₃₁H₅₅NO₁₁
• 分子量: 617.778
• InChiKey: BBQHYPQZGCCXAW-KRLXBADGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  43.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  170.08
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  des-thiomethyllooekeyolide A 在 盐酸 作用下， 以 水 为溶剂， 反应 18.0h， 生成 S-2-羟基丁酸 、 D-亮氨酸
  参考文献：
  名称：

  Chemical and Metagenomic Studies of the Lethal Black Band Disease of Corals Reveal Two Broadly Distributed, Redox-Sensitive Mixed Polyketide/Peptide Macrocycles

  摘要：

  Black band disease (BBD), a lethal, polymicrobial disease consortium dominated by the cyanobacterium Roseof ilum reptotaenium, kills many species of corals worldwide. To uncover chemical signals or cytotoxins that could be important in proliferation of Roseof ilum and the BBD layer, we examined the secondary metabolites present in geographically diverse collections of BBD from Caribbean and Pacific coral reefs. Looekeyolide A (1), a 20-membered macrocyclic compound formed by a 16-carbon polyketide chain, 2deamino-2-hydroxymethionine, and D-leucine, and its autoxidation product looekeyolide B (2) were extracted as major compounds (-4 mg CI dry wt) from more than a dozen field-collected BBD samples. Looekeyolides A and B were also produced by a nonaxenic R reptotaenium culture under laboratory conditions at similar concentrations. R H OH Looekeyolide A OH reptotaenium genomes that were constructed from four different metagenomic data sets contained a unique nonribosomal peptide/polyketide biosynthetic cluster that is likely responsible for the biosynthesis of the looekeyolides. Looekeyolide A, which readily oxidizes to looekeyolide B, may play a biological role in reducing H2O2 and other reactive oxygen species that could occur in the BBD layer as it overgrows and destroys coral tissue.

  DOI：

  10.1021/acs.jnatprod.8b00804
• 作为产物：
  描述：

  C₅₀H₉₃NO₁₁Si₂ 在 盐酸 、 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 SiO₂-supported NaIO₄ 、 2-甲基-6-硝基苯甲酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 41.5h， 生成 des-thiomethyllooekeyolide A
  参考文献：
  名称：

  Total Synthesis of des-Thiomethyllooekeyolide A

  摘要：

  DOI：

  10.1021/acs.orglett.2c02412

文献信息

• Chemical and Metagenomic Studies of the Lethal Black Band Disease of Corals Reveal Two Broadly Distributed, Redox-Sensitive Mixed Polyketide/Peptide Macrocycles
  作者：Sarath P. Gunasekera、Julie L. Meyer、Yousong Ding、Khalil A. Abboud、Danmeng Luo、Justin E. Campbell、Alexander Angerhofer、Justin L. Goodsell、Laurie J. Raymundo、Junyang Liu、Tao Ye、Hendrik Luesch、Max Teplitski、Valerie J. Paul

  DOI：10.1021/acs.jnatprod.8b00804

  日期：2019.1.25

  Black band disease (BBD), a lethal, polymicrobial disease consortium dominated by the cyanobacterium Roseof ilum reptotaenium, kills many species of corals worldwide. To uncover chemical signals or cytotoxins that could be important in proliferation of Roseof ilum and the BBD layer, we examined the secondary metabolites present in geographically diverse collections of BBD from Caribbean and Pacific coral reefs. Looekeyolide A (1), a 20-membered macrocyclic compound formed by a 16-carbon polyketide chain, 2deamino-2-hydroxymethionine, and D-leucine, and its autoxidation product looekeyolide B (2) were extracted as major compounds (-4 mg CI dry wt) from more than a dozen field-collected BBD samples. Looekeyolides A and B were also produced by a nonaxenic R reptotaenium culture under laboratory conditions at similar concentrations. R H OH Looekeyolide A OH reptotaenium genomes that were constructed from four different metagenomic data sets contained a unique nonribosomal peptide/polyketide biosynthetic cluster that is likely responsible for the biosynthesis of the looekeyolides. Looekeyolide A, which readily oxidizes to looekeyolide B, may play a biological role in reducing H2O2 and other reactive oxygen species that could occur in the BBD layer as it overgrows and destroys coral tissue.
• Total Synthesis of <i>des</i>-Thiomethyllooekeyolide A
  作者：Junyang Liu、Ying Chen、Hendrik Luesch、Tao Ye

  DOI：10.1021/acs.orglett.2c02412

  日期：2022.10.14