7,9,9'-Tri-cis-neurosporene | 10467-46-6

• 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: 7,9,9'-Tri-cis-neurosporene
• 英文别名: (6E,8Z,10Z,12E,14E,16E,18E,20E,22Z,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,26,30-dodecaene
• CAS: 10467-46-6
• 化学式: C₄₀H₅₈
• 分子量: 538.9
• InChiKey: ATCICVFRSJQYDV-IFJQPPEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.5
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  7,9,9'-Tri-cis-neurosporene 、 a quinone 生成 prolycopene 、 a quinol
  参考文献：
  名称：

  ?-Carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene

  摘要：

  The plant carotenoid biosynthetic pathway to cyclic carotenes proceeds via carotene precursors in cis configuration. Involvement of individual isomers was elucidated by genetic complementation of desaturations and in vitro reactions of the corresponding enzyme. Determination of substrate and product specificity of phytoene and zeta-carotene desaturase revealed that 15-cis-phytoene is converted to 9,15,9'-tricis-zeta-carotene with 15,9'-dicis-phytofluene as intermediate by the first desaturase. Prior to a subsequent conversion by zeta-carotene desaturase, the 15-cis double bond of 9,15,9'-tricis-zeta-carotene has to be ( photo) isomerized to all-trans. Then, the resulting 9,9'-dicis-zeta-carotene is utilized by zeta-carotene desaturase via 7,9,9'-tricis-neurosporene to 7,9,7', 9'-tetracislycopene. Other zeta-carotene isomers that are assumed to be spontaneous isomerization products were not converted, except for the asymmetric 9-cis-zeta-carotene. This isomer is desaturated only to 7,9-dicis-neurosporene resembling a dead-end of the pathway. Prolycopene, the product of the desaturation reactions, is finally isomerized by a specific isomerase to all-trans-lycopene, which is a prerequisite for cyclization to beta-carotene. The 5-cis-lycopene and the 9-cis-and 13-cis-beta-carotene isomers detected in leaves are thought to originate independently from cis precursors by non-enzymatic isomerization of their all-trans forms.

  DOI：

  10.1007/s00425-004-1395-2
• 作为产物：
  描述：

  (Z)-7-十四碳烯-2-酮 、 a quinone 生成 7,9,9'-Tri-cis-neurosporene 、 a quinol
  参考文献：
  名称：

  ?-Carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene

  摘要：

  The plant carotenoid biosynthetic pathway to cyclic carotenes proceeds via carotene precursors in cis configuration. Involvement of individual isomers was elucidated by genetic complementation of desaturations and in vitro reactions of the corresponding enzyme. Determination of substrate and product specificity of phytoene and zeta-carotene desaturase revealed that 15-cis-phytoene is converted to 9,15,9'-tricis-zeta-carotene with 15,9'-dicis-phytofluene as intermediate by the first desaturase. Prior to a subsequent conversion by zeta-carotene desaturase, the 15-cis double bond of 9,15,9'-tricis-zeta-carotene has to be ( photo) isomerized to all-trans. Then, the resulting 9,9'-dicis-zeta-carotene is utilized by zeta-carotene desaturase via 7,9,9'-tricis-neurosporene to 7,9,7', 9'-tetracislycopene. Other zeta-carotene isomers that are assumed to be spontaneous isomerization products were not converted, except for the asymmetric 9-cis-zeta-carotene. This isomer is desaturated only to 7,9-dicis-neurosporene resembling a dead-end of the pathway. Prolycopene, the product of the desaturation reactions, is finally isomerized by a specific isomerase to all-trans-lycopene, which is a prerequisite for cyclization to beta-carotene. The 5-cis-lycopene and the 9-cis-and 13-cis-beta-carotene isomers detected in leaves are thought to originate independently from cis precursors by non-enzymatic isomerization of their all-trans forms.

  DOI：

  10.1007/s00425-004-1395-2

文献信息

• Biochemical Characterization of Purified zeta-Carotene Desaturase from Anabaena PCC 7120 after Expression in Escherichia coli
  作者：Manuela Albrecht、Hartmut Linden、Gerhard Sandmann

  DOI：10.1111/j.1432-1033.1996.00115.x

  日期：1996.2.15

  A novel enzyme, ζ‐carotene desaturase from the cyanobacterium Anabaena, which catalyzes the last two steps in a series of desaturations, was overexpressed in Escherichia coli. For the first time, this allowed the purification of this enzyme and subsequent enzyme kinetic studies. The enzyme was solubilized from the E. coli membranes by Chaps and purified to homogeneity by ammonium sulfate precipitation, ion‐exchange and hydrophobic interaction chromatography. The correct translational start was confirmed by N‐terminal protein sequencing. Substrates for ζ‐carotene desaturase apart from ζ‐carotene are those carotenes which partially resemble the latter, like neurosporene and β‐zeacarotene yielding lycopene and γ‐carotene, respectively as reaction products. Also cis isomers like pro‐ζ‐carotene were converted to the correspondiong products. Km values of 10 μM were determined for both substrates ζ‐carotene and neurosporene. The enzyme was inhibited to some extent by the experimental herbicides J852 and LS80707 and also by diphenylamine which is a well‐known inhibitor of the bacterial‐type phytoene desaturase.
• ?-Carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene
  作者：J�rgen Breitenbach、Gerhard Sandmann

  DOI：10.1007/s00425-004-1395-2

  日期：2005.3

  The plant carotenoid biosynthetic pathway to cyclic carotenes proceeds via carotene precursors in cis configuration. Involvement of individual isomers was elucidated by genetic complementation of desaturations and in vitro reactions of the corresponding enzyme. Determination of substrate and product specificity of phytoene and zeta-carotene desaturase revealed that 15-cis-phytoene is converted to 9,15,9'-tricis-zeta-carotene with 15,9'-dicis-phytofluene as intermediate by the first desaturase. Prior to a subsequent conversion by zeta-carotene desaturase, the 15-cis double bond of 9,15,9'-tricis-zeta-carotene has to be ( photo) isomerized to all-trans. Then, the resulting 9,9'-dicis-zeta-carotene is utilized by zeta-carotene desaturase via 7,9,9'-tricis-neurosporene to 7,9,7', 9'-tetracislycopene. Other zeta-carotene isomers that are assumed to be spontaneous isomerization products were not converted, except for the asymmetric 9-cis-zeta-carotene. This isomer is desaturated only to 7,9-dicis-neurosporene resembling a dead-end of the pathway. Prolycopene, the product of the desaturation reactions, is finally isomerized by a specific isomerase to all-trans-lycopene, which is a prerequisite for cyclization to beta-carotene. The 5-cis-lycopene and the 9-cis-and 13-cis-beta-carotene isomers detected in leaves are thought to originate independently from cis precursors by non-enzymatic isomerization of their all-trans forms.