12',10-diapocarotene-12',10-dial | 35482-79-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12',10-diapocarotene-12',10-dial
• 英文别名: C12-apocarotene-dialdehyde；(all-E)-2,7-dimethyl-deca-2,4,6,8-tetraenedial；2,7-Dimethyl-deca-2,4,6,8-tetraenedial；(2E,4E,6E,8E)-2,7-dimethyldeca-2,4,6,8-tetraenedial
• CAS: 35482-79-2
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: GFXWLWOPYGKKOJ-SZZOTQSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  fucoxanthin 在 zinc(II) permanganate 作用下， 以 丙酮 为溶剂， 生成 12',10-diapocarotene-12',10-dial
  参考文献：
  名称：

  类胡萝卜素和相关化合物。第XX部分。岩藻黄质的结构与反应

  摘要：

  岩藻黄质是一种Allenic类胡萝卜素。化学和光谱研究确定其结构为3'-乙酰氧基-5,6-环氧-3,5'-二羟基-6'，7'-二氢-5,6,7,8,5'，6'-六氢- β-caroten-8-one（15）。

  DOI：

  10.1039/j39690000429

文献信息

• Synthesen in der Carotinoid-Reihe 23. Mitteilung Ein Beitrag zur Chromsäure-Oxydation von Polyenen
  作者：U. Schwieter、W. Arnold、W. E. Oberhänsli、N. Rigassi、W. Vetter

  DOI：10.1002/hlca.19710540808

  日期：1971.12.10

  Chromic acid oxidation of polyenes with terminal β-ionylidene groups has been studied. A number of hitherto unknown and unexpected oxidation products has been isolated. A mechanism for these oxidations is discussed.

  研究了带有末端β-亚硫基的多烯的铬酸氧化。已经分离出许多迄今未知和意外的氧化产物。讨论了这些氧化的机理。
• The human mitochondrial enzyme BCO2 exhibits catalytic activity toward carotenoids and apocarotenoids
  作者：Linda D. Thomas、Sepalika Bandara、Vipulkumar M. Parmar、Ramkumar Srinivasagan、Nimesh Khadka、Marcin Golczak、Philip D. Kiser、Johannes von Lintig

  DOI：10.1074/jbc.ra120.015515

  日期：2020.11

  The enzyme beta-carotene oxygenase 2 (BCO2) converts carotenoids into more polar metabolites. Studies in mammals, fish, and birds revealed that BCO2 controls carotenoid homeostasis and is involved in the pathway for vitamin A production. However, it is controversial whether BCO2 function is conserved in humans, because of a 4-amino acid long insertion caused by a splice acceptor site polymorphism. We here show that human BCO2 splice variants, BCO2a and BCO2b, are expressed as pre-proteins with mitochondrial targeting sequence (MTS). The MTS of BCO2a directed a green fluorescent reporter protein to the mitochondria when expressed in ARPE-19 cells. Removal of the MTS increased solubility of BCO2a when expressed in Escherichia coli and rendered the recombinant protein enzymatically active. The expression of the enzymatically active recombinant human BCO2a was further improved by codon optimization and its fusion with maltose-binding protein. Introduction of the 4-amino acid insertion into mouse Bco2 did not impede the chimeric enzyme's catalytic proficiency. We further showed that the chimeric BCO2 displayed broad substrate specificity and converted carotenoids into two ionones and a central C14-apocarotendial by oxidative cleavage reactions at C9,C10 and C9',C10'. Thus, our study demonstrates that human BCO2 is a catalytically competent enzyme. Consequently, information on BCO2 becomes broadly applicable in human biology with important implications for the physiology of the eyes and other tissues.