bilirubin

• 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: bilirubin
• 英文别名: bilirubin XIII-α；3-[2-[[3-(2-carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid
• 化学式: C₃₃H₃₆N₄O₆
• 分子量: 584.672
• InChiKey: SJDJRWBCNPRKRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  164
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bilirubin 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 bilirubin IXα diamide
  参考文献：
  名称：

  Biliverdin Amides Reveal Roles for Propionate Side Chains in Bilin Reductase Recognition and in Holophytochrome Assembly and Photoconversion

  摘要：

  Linear tetrapyrroles (bilins) perform important antioxidant and light-harvesting functions in cells from bacteria to humans. To explore the role of the propionate moieties in bilin metabolism, we report the semisynthesis of mono- and diamides of biliverdin IX alpha and those of its non-natural XIII alpha isomer. Initially, these were examined as substrates of two types of NADPH-dependent biliverdin reductase, BVR and BvdR, and of the representative ferredoxin-dependent bilin reductase, phycocyanobilin:ferredoxin oxidoreductase (PcyA). Our studies indicate that the NADPH-dependent biliverdin reductases are less accommodating to amidation of the propionic acid side chains of biliverdin IX alpha than PcyA, which does not require free carboxylic acid side chains to yield its phytobilin product, phycocyanobilin. Bilin amides were also assembled with BV-type and phytobilin-type apophytochromes, demonstrating a role for the 8-propionate in the formation of the spectroscopically native P-r dark states of these biliprotein photosensors. Neither ionizable propionate side chain proved to be essential to primary photoisomerization for both classes of phytochromes, but an unsubstituted 12-propionate was required for full photointerconversion of phytobilin-type phytochrome Cph1. Taken together, these studies provide insight into the roles of the ionizable propionate side chains in substrate discrimination by two bilin reductase families while further underscoring the mechanistic differences between the photoconversions of BV-type and phytobilin-type phytochromes.

  DOI：

  10.1021/bi100756x
• 作为产物：
  描述：

  在 哌啶 、 硫酸 、 溶剂黄146 、 copper(l) chloride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 61.0h， 生成 bilirubin
  参考文献：
  名称：

  [EN] METHOD FOR SYNTHESIZING BILIRUBIN
  [FR] PROCÉDÉ DE SYNTHÈSE DE BILIRUBINE
  [KO] 빌리루빈의 합성 방법

  摘要：

  본 발명은 빌리루빈의 합성 방법에 관한 것으로서, 보다 상세하게는 화학식 1로 표시되는 화합물과 화학식 2로 표시되는 화합물을 커플링시켜 화학식 3으로 표시되는 화합물을 제조하는 단계를 포함함으로써 의약품 등으로 유용하게 활용되는 빌리루빈 및 페길화된 빌리루빈을 최초로 화학적으로 합성한 방법에 관한 것이다.

  公开号：

  WO2023018217A1

文献信息

• Biliverdin Amides Reveal Roles for Propionate Side Chains in Bilin Reductase Recognition and in Holophytochrome Assembly and Photoconversion
  作者：Lixia Shang、Nathan C. Rockwell、Shelley S. Martin、J. Clark Lagarias

  DOI：10.1021/bi100756x

  日期：2010.7.27

  Linear tetrapyrroles (bilins) perform important antioxidant and light-harvesting functions in cells from bacteria to humans. To explore the role of the propionate moieties in bilin metabolism, we report the semisynthesis of mono- and diamides of biliverdin IX alpha and those of its non-natural XIII alpha isomer. Initially, these were examined as substrates of two types of NADPH-dependent biliverdin reductase, BVR and BvdR, and of the representative ferredoxin-dependent bilin reductase, phycocyanobilin:ferredoxin oxidoreductase (PcyA). Our studies indicate that the NADPH-dependent biliverdin reductases are less accommodating to amidation of the propionic acid side chains of biliverdin IX alpha than PcyA, which does not require free carboxylic acid side chains to yield its phytobilin product, phycocyanobilin. Bilin amides were also assembled with BV-type and phytobilin-type apophytochromes, demonstrating a role for the 8-propionate in the formation of the spectroscopically native P-r dark states of these biliprotein photosensors. Neither ionizable propionate side chain proved to be essential to primary photoisomerization for both classes of phytochromes, but an unsubstituted 12-propionate was required for full photointerconversion of phytobilin-type phytochrome Cph1. Taken together, these studies provide insight into the roles of the ionizable propionate side chains in substrate discrimination by two bilin reductase families while further underscoring the mechanistic differences between the photoconversions of BV-type and phytobilin-type phytochromes.
• [EN] METHOD FOR SYNTHESIZING BILIRUBIN<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE BILIRUBINE<br/>[KO] 빌리루빈의 합성 방법
  申请人：[en]BILIX CO., LTD.;[ko]주식회사 빌릭스

  公开号：WO2023018217A1

  公开（公告）日：2023-02-16

  본 발명은 빌리루빈의 합성 방법에 관한 것으로서, 보다 상세하게는 화학식 1로 표시되는 화합물과 화학식 2로 표시되는 화합물을 커플링시켜 화학식 3으로 표시되는 화합물을 제조하는 단계를 포함함으로써 의약품 등으로 유용하게 활용되는 빌리루빈 및 페길화된 빌리루빈을 최초로 화학적으로 합성한 방법에 관한 것이다.