3,3'-(3,7,12,17-tetramethyl-1,19-dioxo-8,13-divinyl-1,19,22,24-tetrahydro-21H-biline-2,18-diyl)-bis-propionic acid dimethyl ester | 26280-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 3,3'-(3,7,12,17-tetramethyl-1,19-dioxo-8,13-divinyl-1,19,22,24-tetrahydro-21H-biline-2,18-diyl)-bis-propionic acid dimethyl ester
• 英文别名: biliverdin IX_γ dimethyl ester；γ-biliverdin-IX dimethyl ester；biliverdin IX γ dimethyl ester
• CAS: 26280-00-2
• 化学式: C₃₅H₃₈N₄O₆
• 分子量: 610.71
• InChiKey: BKJQAYAVJLILPL-RUXNVCPMSA-N

物化性质

• 沸点：
  862.2±65.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  45.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  138.95
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3,3'-(3,7,12,17-tetramethyl-1,19-dioxo-8,13-divinyl-1,19,22,24-tetrahydro-21H-biline-2,18-diyl)-bis-propionic acid dimethyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 γ-biliverdin-IX
  参考文献：
  名称：

  biliverdin-IX在人体中的尿液排泄。

  摘要：

  使用来自七个健康成年人的尿液样本研究了α-，β-，γ-和δ-胆小素-IX的四个异构体的分布和相对比例。将来自样品的联肝素吸附在滑石上，然后将吸附的联肝素浸入甲醇和浓硫酸的溶液中，以衍生为二甲基酯。将酯送入反相柱中进行纯化，然后在反相柱上通过HPLC进行定量。分析显示，在24小时尿液中的biliverdins由6.4 +/- 2.5 nmolα-和9.3 +/- 5.4 nmolβ-异构体组成。HPLC分析表明，δ-异构体的存在量要少得多，但没有检测到γ-异构体。α-和β-异构体的鉴定通过共色谱和吸收光谱进行。

  DOI：

  10.1248/bpb.18.481
• 作为产物：
  描述：

  γ-benzyloxyprotopophyrin IX dimethyl ester 生成 3,3'-(3,7,12,17-tetramethyl-1,19-dioxo-8,13-divinyl-1,19,22,24-tetrahydro-21H-biline-2,18-diyl)-bis-propionic acid dimethyl ester
  参考文献：
  名称：

  四个合成介- oxyprotoporphyrin异构体

  摘要：

  的四种异构体的内消旋- oxyprotoporphrin二甲基酯已经制备通过原卟啉IX dimehtyl酯，通过HPLC分离，并identifide的直接氧化通过转化成相应的biliverdins。

  DOI：

  10.1039/c39820000794

文献信息

• Synthesis of γ-oxyprotoporphyrin IX and pterobiline (biliverdin IX_γ)
  作者：Anthony H. Jackson、Rhiannydd M. Jenkins、D. Michael Jones、Stephen A. Matlin

  DOI：10.1039/c39810000763

  日期：——

  The γ-meso-hydroxy-derivative of protopor-phyrin IX has been synthesised by condensation of a bis(formylpyrroly) ketone and a dispyrrolylmethane; the iron complex underwent oxidative ring-opening to give biliverdin IXγ(ptrobiline), the blue -green butterfly pigment, thus providing a modle for its biosynthesis.

  的γ -内消旋-羟基衍生物protopor-卟啉IX的已经由双（formylpyrroly）酮和dispyrrolylmethane的缩合合成; 铁络合物后行氧化开环，得到胆绿素IX γ（ptrobiline），蓝-绿色颜料蝴蝶，从而提供了其生物合成的模型。。
• Heme-iron utilization by Leptospira interrogans requires a heme oxygenase and a plastidic-type ferredoxin-NADP+ reductase
  作者：Anabel Soldano、Huili Yao、Mario Rivera、Eduardo A. Ceccarelli、Daniela L. Catalano-Dupuy

  DOI：10.1016/j.bbagen.2014.07.021

  日期：2014.11

  Background: Heme oxygenase catalyzes the conversion of heme to iron, carbon monoxide and biliverdin employing oxygen and reducing equivalents. This enzyme is essential for heme-iron utilization and contributes to virulence in Leptospira interrogans. Methods: A phylogenetic analysis was performed using heme oxygenases sequences from different organisms including saprophytic and pathogenic Leptospira species. L. interrogans heme oxygenase (LepHO) was cloned, overexpressed and purified. The structural and enzymatic properties of LepHO were analyzed by UV-vis spectrophotometry and (1)H NMR. Heme-degrading activity, ferrous iron release and biliverdin production were studied with different redox partners. Results: A plastidic type, high efficiently ferredoxin-NADP(+) reductase (LepFNR) provides the electrons for heme turnover by heme oxygenase in L. interrogans. This catalytic reaction does not require a ferredoxin. Moreover, LepFNR drives the heme degradation to completeness producing free iron and α-biliverdin as the final products. The phylogenetic divergence between heme oxygenases from saprophytic and pathogenic species supports the functional role of this enzyme in L. interrogans pathogenesis. Conclusions: Heme-iron scavenging by LepHO in L. interrogans requires only LepFNR as redox partner. Thus, we report a new substrate of ferredoxin-NADP(+) reductases different to ferredoxin and flavodoxin, the only recognized protein substrates of this flavoenzyme to date. The results presented here uncover a fundamental step of heme degradation in L. interrogans. General significance: Our findings contribute to understand the heme-iron utilization pathway in Leptospira. Since iron is required for pathogen survival and infectivity, heme degradation pathway may be relevant for therapeutic applications.
• Synthesis of biliverdin IXγ (pterobilin)
  作者：Anthony H. Jackson、Rhianydd M. Jenkins、D.Michael Jones、Stephen A. Matlin

  DOI：10.1016/s0040-4020(01)88698-1

  日期：1983.1
• Synthesis of the four meso- oxyprotoporphyrin isomers
  作者：Anthony H. Jackson、K. R. Nagaraja Rao、Martyn Wilkins

  DOI：10.1039/c39820000794

  日期：——

  The four isomers of meso- oxyprotoporphrin dimethyl esters have been prepared via direct oxidation of protoporphyrin IX dimehtyl ester, separated by h.p.l.c., and identifide by conversion into the corresponding biliverdins.

  的四种异构体的内消旋- oxyprotoporphrin二甲基酯已经制备通过原卟啉IX dimehtyl酯，通过HPLC分离，并identifide的直接氧化通过转化成相应的biliverdins。
• Urinary Excretion of .ALPHA.- and .BETA.-Isomers of Biliverdin-IX in Humans.
  作者：Kazuhiro HIROTA

  DOI：10.1248/bpb.18.481

  日期：——

  investigated using urinary samples from seven healthy adults. The biliverdins from samples were adsorbed on talc, and the adsorbed biliverdins were then soaked in a solution of methanol and concentrated sulfuric acid for derivation to the dimethyl esters. The esters were passed to a reversed-phase cartridge for clean-up, then quantitated by HPLC on a reversed-phase column. The analyses revealed that the biliverdins

  使用来自七个健康成年人的尿液样本研究了α-，β-，γ-和δ-胆小素-IX的四个异构体的分布和相对比例。将来自样品的联肝素吸附在滑石上，然后将吸附的联肝素浸入甲醇和浓硫酸的溶液中，以衍生为二甲基酯。将酯送入反相柱中进行纯化，然后在反相柱上通过HPLC进行定量。分析显示，在24小时尿液中的biliverdins由6.4 +/- 2.5 nmolα-和9.3 +/- 5.4 nmolβ-异构体组成。HPLC分析表明，δ-异构体的存在量要少得多，但没有检测到γ-异构体。α-和β-异构体的鉴定通过共色谱和吸收光谱进行。