luminmycin A | 1394140-12-5

• 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: luminmycin A
• 英文别名: Luminmycin A；(2E,4E)-N-[(2S,3R)-3-hydroxy-1-[[(3E,5S,8S)-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl]amino]-1-oxobutan-2-yl]dodeca-2,4-dienamide
• CAS: 1394140-12-5
• 化学式: C₂₇H₄₄N₄O₅
• 分子量: 504.67
• InChiKey: CXVPCSSIDACGGV-SBSLBVBZSA-N

物化性质

• 沸点：
  855.5±65.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  luminmycin A 在 盐酸 作用下， 以 水 为溶剂， 反应 16.0h， 生成 L-苏氨酸 、 L-赖氨酸
  参考文献：
  名称：

  Luminmycins A–C, Cryptic Natural Products from Photorhabdus luminescens Identified by Heterologous Expression in Escherichia coli

  摘要：

  The 18 kb "silent" luminmycin biosynthetic pathway from Photorhabdus luminescens was cloned into a vector by using the newly established linear-linear homologous recombination and successfully expressed in Escherichia coli. Luminmycins A-C (1-3) were isolated from the heterologous host, and their structures were elucidated using 2D NMR spectroscopy and HRESIMS. Luminmycin A is a deoxy derivative of the previously reported glidobactin A, while luminmycins B and C most likely represent its acyclic biosynthetic intermediates. Compound 1 showed cytotoxicity against the human colon carcinoma HCT-116 cell line with an IC50 value of 91.8 nM, while acyclic 2 was inactive at concentrations as high as 100 mu g/mL.

  DOI：

  10.1021/np300444e
• 作为产物：
  描述：

  2-dodecynoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 24.5h， 生成 luminmycin A
  参考文献：
  名称：

  夜光霉素的一种隐性天然产物，Luminmycin A的全合成

  摘要：

  首次合成了天然蛋白酶体抑制剂LuminmycinA。关键步骤是分子内霍纳-沃兹沃思-埃蒙斯反应和炔属脂肪酸酯的PPh 3催化异构化，从而可以进入双不饱和脂肪酸侧链。

  DOI：

  10.1002/ejoc.201900460

文献信息

• Total Synthesis of Luminmycin A, a Cryptic Natural Product from <i>Photorhabdus Luminescens</i>
  作者：Phil Servatius、Tanja Stach、Uli Kazmaier

  DOI：10.1002/ejoc.201900460

  日期：2019.6.2

  Luminmycin A, a natural proteasome inhibitor has been synthesized for the first time. Key steps are an intramolecular Horner–Wadsworth–Emmons reaction and a PPh3‐catalyzed isomerization of a acetylenic fatty acid ester, giving access to the double unsaturated fatty acid side chain.

  首次合成了天然蛋白酶体抑制剂LuminmycinA。关键步骤是分子内霍纳-沃兹沃思-埃蒙斯反应和炔属脂肪酸酯的PPh 3催化异构化，从而可以进入双不饱和脂肪酸侧链。
• Luminmycins A–C, Cryptic Natural Products from <i>Photorhabdus luminescens</i> Identified by Heterologous Expression in <i>Escherichia coli</i>
  作者：Xiaoying Bian、Alberto Plaza、Youming Zhang、Rolf Müller

  DOI：10.1021/np300444e

  日期：2012.9.28

  The 18 kb "silent" luminmycin biosynthetic pathway from Photorhabdus luminescens was cloned into a vector by using the newly established linear-linear homologous recombination and successfully expressed in Escherichia coli. Luminmycins A-C (1-3) were isolated from the heterologous host, and their structures were elucidated using 2D NMR spectroscopy and HRESIMS. Luminmycin A is a deoxy derivative of the previously reported glidobactin A, while luminmycins B and C most likely represent its acyclic biosynthetic intermediates. Compound 1 showed cytotoxicity against the human colon carcinoma HCT-116 cell line with an IC50 value of 91.8 nM, while acyclic 2 was inactive at concentrations as high as 100 mu g/mL.