2-methyl-3-((all-E)-3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,10,14,18,22,26,30,34-octaenyl)-[1,4]naphthoquinone | 19479-25-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-methyl-3-((all-E)-3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,10,14,18,22,26,30,34-octaenyl)-[1,4]naphthoquinone
• 英文别名: Dihydromenaquinone-9；2-methyl-3-[(2E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,10,14,18,22,26,30,34-octaenyl]naphthalene-1,4-dione
• CAS: 19479-25-5
• 化学式: C₅₆H₈₂O₂
• 分子量: 787.266
• InChiKey: SJOKRFJLUXNKIK-ISIUCFNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.2
• 重原子数：
  58
• 可旋转键数：
  27
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-3-((all-E)-3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,10,14,18,22,26,30,34-octaenyl)-[1,4]naphthoquinone 在 氧气 作用下， 以 环己烷 为溶剂， 生成 2,6,10,14,18,22,26,30-Oktamethyl-pentatriakontaheptaen-(2.6.10.14.18.22.26)
  参考文献：
  名称：

  Photooxygenation of phylloquinone and menaquinones

  摘要：

  DOI：

  10.1021/ja01031a039
• 作为产物：
  描述：

  AH₂ 、 维生素 K2(45) 生成 A 、 2-methyl-3-((all-E)-3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,10,14,18,22,26,30,34-octaenyl)-[1,4]naphthoquinone
  参考文献：
  名称：

  Partial Saturation of Menaquinone in Mycobacterium tuberculosis: Function and Essentiality of a Novel Reductase, MenJ

  摘要：

  Menaquinone (MK) with partially saturated isoprenyl moieties is found in a wide range of eubacteria and Archaea. In many Gram-positive organisms, including mycobacteria, it is the double bond found in the beta-isoprene unit that is reduced. Mass spectral characterization of menaquinone from mycobacterial knockout strains and heterologous expression hosts demonstrates that Rv0561c (designated menJ) encodes an enzyme which reduces the beta-isoprene unit of menaquinone in Mycobacterium tuberculosis, forming the predominant form of menaquinone found in mycobacteria. MenJ is highly conserved in mycobacteria species but is not required for growth in culture. Disruption of menJ reduces mycobacterial electron transport efficiency by 3-fold, but mycobacteria are able to maintain ATP levels by increasing the levels of the total menaquinone in the membrane; however, MenJ is required for M. tuberculosis survival in host macrophages. Thus, MK with partially hydrogenated isoprenyl moieties represents a novel virulence factor and MenJ is a contextually essential enzyme and a potential drug target in pathogenic mycobacteria and other Gram-positive pathogens.

  DOI：

  10.1021/acscentsci.5b00212

文献信息

• Structural Characterization of a Novel Sulfated Menaquinone produced by <i>stf3</i> from <i>Mycobacterium tuberculosis</i>
  作者：Cynthia M. Holsclaw、Kimberly M. Sogi、Sarah A. Gilmore、Michael W. Schelle、Michael D. Leavell、Carolyn R. Bertozzi、Julie A. Leary

  DOI：10.1021/cb800145r

  日期：2008.10.17

  Mycobacterium tuberculosis, the causative agent of tuberculosis, produces unique sulfated metabolites associated with virulence. One such metabolite from M. tuberculosis lipid extracts, S881, has been shown to negatively regulate the virulence of M. tuberculosis in mouse infection studies, and its cell-surface localization suggests a role in modulating host-pathogen interactions. However, a detailed structural analysis of S881 has remained elusive. Here we use high-resolution, high-mass-accuracy, and tandem mass spectrometry to characterize the structure of S881. Exact mass measurements showed that S881 is highly unsaturated, tandem mass spectrometry indicated a polyisoprene-derived structure, and characterization of synthetic structural analogs confirmed that S881 is a previously undescribed sulfated derivative of dihydromenaquinone-9, the primary quinol electron carrier in M. tuberculosis. To our knowledge, this is the first example of a sulfated menaquinone produced in any prokaryote. Together with previous studies, these findings suggest that this redox cofactor may play a role in mycobacterial pathogenesis.
• Biosynthesis and Regulation of Sulfomenaquinone, a Metabolite Associated with Virulence in <i>Mycobacterium tuberculosis</i>
  作者：Kimberly M. Sogi、Cynthia M. Holsclaw、Gabriela K. Fragiadakis、Daniel K. Nomura、Julie A. Leary、Carolyn R. Bertozzi

  DOI：10.1021/acsinfecdis.6b00106

  日期：2016.11.11

  Sulfomenaquinone (SMK) is a recently identified metabolite that is unique to the Mycobacterium tuberculosis (M. tuberculosis) complex and is shown to modulate its virulence. Here, we report the identification of the SMK biosynthetic operon that, in addition to a previously identified sulfotransferase stf3, includes a putative cytochrome P450 gene (cyp128) and a gene of unknown function, rv2269c. We demonstrate that cyp128 and stf3 are sufficient for the biosynthesis of SMK from menaquinone and rv2269c exhibits promoter activity in M. tuberculosis. Loss of Stf3 expression, but not that of Cyp128, is correlated with elevated levels of menaquinone-9, an essential component in the electron transport chain in M. tuberculosis. Finally, we showed in a mouse model of infection that the loss of cyp128 exhibits a hypervirulent phenotype similar to that in previous studies of the stf3 mutant. These findings provide a platform for defining the molecular basis of SMK's role in M. tuberculosis pathogenesis.