(+)-phomopsidin | 199173-60-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+)-phomopsidin
• 英文别名: Phomopsidin；(2E,4E)-5-[(1S,2R,4aS,5S,8S,8aS)-2-[(E)-but-2-en-2-yl]-5-hydroxy-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]penta-2,4-dienoic acid
• CAS: 199173-60-9
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: KNDPLJZJPQWOMQ-FDTXVGEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-phomopsidin 在 4-二甲氨基吡啶 作用下， 以 吡啶 、 甲醇 、 正己烷 、 苯 为溶剂， 反应 0.5h， 生成 4-Nitro-benzoic acid (1S,4S,4aS,5S,6R,8aS)-5-((1E,3E)-4-methoxycarbonyl-buta-1,3-dienyl)-4,7-dimethyl-6-((E)-1-methyl-propenyl)-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl ester
  参考文献：
  名称：

  Absolute structure, biosynthesis, and anti-microtubule activity of phomopsidin, isolated from a marine-derived fungus Phomopsis sp.

  摘要：

  The absolute configuration of phomopsidin, a marine-derived fungal metabolite from Phomopsis sp. isolated at Pohnpei, was determined by the exciton chirality method as 6S, 7S, 8S, 11S, 12R, and 15R. The biosynthetic study using C-13-labeled precursors revealed the origin of all carbon atoms in phomopsidin, which was built by nine acetates and three methyl groups from L-methionine. Inhibitory activities of phomopsidin and its Me ester derivative against microtubule assembly were examined together with the structurally related compounds MK8383, solanapyrones, and tanzawaic acids. Phomopsidin and its (16Z)-isomer (MK8383) showed anti-microtubule activity at IC50 of 5.7 and 8.0 muM, respectively, while the Me ester and other compounds were not active at 100 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01566-1
• 作为产物：
  描述：

  Benzoic acid (1S,4S,4aS,5S,6R,8aS)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,7-dimethyl-6-((E)-1-methyl-propenyl)-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl ester 在 lithium hydroxide 、 四丁基氟化铵 、 戴斯-马丁氧化剂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 生成 (+)-phomopsidin
  参考文献：
  名称：

  第一次全合成抗有丝分裂化合物，（+）-phomopsidin。

  摘要：

  [反应：见正文]通过非对映选择性的跨环Diels-Alder（TADA）反应，实现了（+）-磷酸抗霉菌素的第一个全合成。合成的关键步骤包括用（-）-α-pine烯和9-BBN进行非对映选择性的炔酮还原，通过E-选择性分子内Horner-Wadsworth-Emmons（HWE）反应进行大环化，以及在Wipf条件下进行碳金属化，然后进行HWE反应在低温下选择性地构建（E）-1-甲基丙烯基和（1E，2E）-4-羧基-1,3-丁二烯基取代基。

  DOI：

  10.1021/ol036338q

文献信息

• Antimicrobials from an epigenetics based fungal metabolite screening program
  申请人：Demers Danielle H.

  公开号：US10144719B1

  公开（公告）日：2018-12-04

  Novel antimicrobial compounds against drug targets such as Eskape pathogens, Leishmania donovani, Mycobacterium tuberculosis, Clostridium difficile, Naegleria fowleri, and cancer are presented herein.

  本文介绍了针对 Eskape 病原体、唐氏利什曼原虫、结核分枝杆菌、艰难梭菌、奈格勒氏菌和癌症等药物靶标的新型抗菌化合物。
• Establishment of cellular manipulations which enhance oligo-mediated gene targeting
  申请人：——

  公开号：US20030211612A1

  公开（公告）日：2003-11-13

  The invention relates to improved methods for the modification, including recombination, of genes in cells. More specifically, the invention relates to the increased efficiency of modification, including recombination, by introduction of a DNA-modifying molecule into a cell cycle synchronized cell. Additionally, the invention relates to target DNA that has been modified, mutated or marked by the approaches disclosed herein. The invention also relates to cells, tissue, and organisms which have been modified by the invention's methods.

  本发明涉及细胞中基因修饰（包括重组）的改进方法。更具体地说，本发明涉及通过将 DNA 修饰分子引入细胞周期同步化细胞来提高修饰（包括重组）的效率。此外，本发明还涉及通过本文公开的方法修饰、突变或标记的目标 DNA。本发明还涉及用本发明方法修饰过的细胞、组织和生物体。
• NOVEL MK8383 ANALOGUE AND DISEASE CONTROL AGENT FOR AGRICULTURAL OR HORTICULTURAL PURPOSES
  申请人：Meiji Seika Pharma Co., Ltd.

  公开号：EP2261197B1

  公开（公告）日：2013-08-07
• DNA modifying molecules and methods of use thereof
  申请人：The Government of the U.S.A. as represented by the Secretary of the Dept. of Health & Human Services

  公开号：US20040009602A1

  公开（公告）日：2004-01-15

  In one aspect, the disclosure concerns improved methods for the modification of genes in cells. Particular methods accomplish recombination, including targeted homologous recombination of a target gene. In another aspect, the disclosure relates to DNA modifying molecules. In one aspect, DNA modifying molecules comprise DNA targeting agents, including modified oligonucleotides, including triplex forming oligonucleotides, peptide nucleic acids and polyamides. In one embodiment, the DNA modifying molecules comprise a mutagen, and in another embodiment the DNA modifying molecules comprise a mutagen and a DNA targeting agent. The disclosure also describes methods for modifying a nucleotide sequence in the genome of a cell using the DNA targeting agents. The disclosure also relates to cells, tissue, and organisms that have been modified by DNA targeting agents.
• NOVEL SUBSTANCES ANALOGOUS TO MK8383 AND AGRICULTURAL AND HORTICULTURAL DISEASE CONTROL AGENTS
  申请人：Yamamoto Kentaro

  公开号：US20110065792A1

  公开（公告）日：2011-03-17

  An objective of the present invention is to provide agricultural and horticultural disease control agents that have potent control effect against plant diseases and, at the same time, have high photostability. The agricultural and horticultural disease control agents comprise a novel substance analogous to MK8383 as an active ingredient.