N-(5-羟基-5-(7-((2-羟基-5-氧代-1-环戊烯-1-基)氨基)-7-氧代-1,3,5-庚三烯基)-2-氧代-7-氧杂双环(4.1.0)庚-3-烯-3-基)-8-甲基-2,4,6-壬三烯酰胺 | 156250-44-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N-(5-羟基-5-(7-((2-羟基-5-氧代-1-环戊烯-1-基)氨基)-7-氧代-1,3,5-庚三烯基)-2-氧代-7-氧杂双环(4.1.0)庚-3-烯-3-基)-8-甲基-2,4,6-壬三烯酰胺
• 英文名称: (2E,4E,6E)-8-Methyl-nona-2,4,6-trienoic acid {(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-6-(2-hydroxy-5-oxo-cyclopent-1-enylcarbamoyl)-hexa-1,3,5-trienyl]-2-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl}-amide
• 英文别名: Manumycin G；(2E,4E,6E)-N-[(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopenten-1-yl)amino]-7-oxohepta-1,3,5-trienyl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-8-methylnona-2,4,6-trienamide
• CAS: 156250-44-1
• 化学式: C₂₈H₃₀N₂O₇
• 分子量: 506.555
• InChiKey: WIFRXHSYMJBOJD-WRSGMFNISA-N

物化性质

• 沸点：
  876.1±65.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(5-羟基-5-(7-((2-羟基-5-氧代-1-环戊烯-1-基)氨基)-7-氧代-1,3,5-庚三烯基)-2-氧代-7-氧杂双环(4.1.0)庚-3-烯-3-基)-8-甲基-2,4,6-壬三烯酰胺 在 chromium(VI) oxide 、 溶剂黄146 作用下， 反应 7.0h， 以0.16 mg的产率得到(2E,4E,6E)-8-Methyl-nona-2,4,6-trienoic acid ((1S,6R)-2,5-dioxo-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-amide
  参考文献：
  名称：

  EI-1511-3, -S and EI-1625-2, Novel Interleukin-l.BETA. Conveffing Enzyme Inhibitors Produced by Streptomyces sp. E-1511 and E-1625. II. Structure Determination.

  摘要：

  The structures of three novel interleukin-1β converting enzyme inhibitors, EI-1511-3, -5 and EI-1625-2 were determined by spectroscopic methods. Their absolute configurations were also determined by analyses of the CD spectra of the inhibitors and their oxidation products with chromium trioxide.

  DOI：

  10.7164/antibiotics.49.1079
• 作为产物：
  描述：

  在 flavin-dependent-4-hydroxyprotoasukamycin epoxidase AsuE₃, 41 kDa 、 2,6-蒽二酚 、 还原型辅酶Ⅰ 作用下， 以 aq. phosphate buffer 为溶剂， 生成 N-(5-羟基-5-(7-((2-羟基-5-氧代-1-环戊烯-1-基)氨基)-7-氧代-1,3,5-庚三烯基)-2-氧代-7-氧杂双环(4.1.0)庚-3-烯-3-基)-8-甲基-2,4,6-壬三烯酰胺
  参考文献：
  名称：

  Tandem Enzymatic Oxygenations in Biosynthesis of Epoxyquinone Pharmacophore of Manumycin-type Metabolites

  摘要：

  Many natural products contain epoxyquinone pharmacophore with unknown biosynthetic mechanisms. Recent genetic analysis of the asukamycin biosynthetic gene cluster proposed enzyme candidates related to epoxyquinone formation for manumycin-type metabolites. Our biochemical studies reveal that 3-amino-4-hydroxyl benzoic acid (3,4-AHBA) precursor is activated and loaded on aryl carrier protein (AsuC12) by ATP-dependent adenylase (AsuA2). AsuE1 and AsuE3, both single-component flavin-dependent monooxygenases, catalyze the exquisite regio- and enantiospecific postpolyketide synthase (PKS) assembly oxygenations. AsuE1 installs a hydroxyl group on the 3,4-AHB ring to form a 4-hydroxyquinone moiety, which is epoxidized by AsuE3 to yield the epoxyquinone functionality. Despite being a single-component monooxygenase, AsuE1 activity is elicited by AsuE2, a pathway-specific flavin reductase. We further demonstrate that the epoxyquinone moiety is critical for anti-MRSA activity by analyzing the bioactivity of various manumycin-type metabolites produced through mutasynthesis.

  DOI：

  10.1016/j.chembiol.2013.05.006

文献信息

• Tandem Enzymatic Oxygenations in Biosynthesis of Epoxyquinone Pharmacophore of Manumycin-type Metabolites
  作者：Zhe Rui、Moriah Sandy、Brian Jung、Wenjun Zhang

  DOI：10.1016/j.chembiol.2013.05.006

  日期：2013.7

  Many natural products contain epoxyquinone pharmacophore with unknown biosynthetic mechanisms. Recent genetic analysis of the asukamycin biosynthetic gene cluster proposed enzyme candidates related to epoxyquinone formation for manumycin-type metabolites. Our biochemical studies reveal that 3-amino-4-hydroxyl benzoic acid (3,4-AHBA) precursor is activated and loaded on aryl carrier protein (AsuC12) by ATP-dependent adenylase (AsuA2). AsuE1 and AsuE3, both single-component flavin-dependent monooxygenases, catalyze the exquisite regio- and enantiospecific postpolyketide synthase (PKS) assembly oxygenations. AsuE1 installs a hydroxyl group on the 3,4-AHB ring to form a 4-hydroxyquinone moiety, which is epoxidized by AsuE3 to yield the epoxyquinone functionality. Despite being a single-component monooxygenase, AsuE1 activity is elicited by AsuE2, a pathway-specific flavin reductase. We further demonstrate that the epoxyquinone moiety is critical for anti-MRSA activity by analyzing the bioactivity of various manumycin-type metabolites produced through mutasynthesis.
• EI-1511-3, -S and EI-1625-2, Novel Interleukin-l.BETA. Conveffing Enzyme Inhibitors Produced by Streptomyces sp. E-1511 and E-1625. II. Structure Determination.
  作者：YOUICHI UOSAKI、TSUTOMU AGATSUMA、TAKEO TANAKA、YUTAKA SAITOH

  DOI：10.7164/antibiotics.49.1079

  日期：——

  The structures of three novel interleukin-1β converting enzyme inhibitors, EI-1511-3, -5 and EI-1625-2 were determined by spectroscopic methods. Their absolute configurations were also determined by analyses of the CD spectra of the inhibitors and their oxidation products with chromium trioxide.