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A visible-light activated [2 + 2] cycloaddition reaction enables pinpointing carbon–carbon double bonds in lipids
Chemical Science ( IF 7.6 ) Pub Date : 2020-06-22 , DOI: 10.1039/d0sc01149e Guifang Feng 1 , Yanhong Hao 1 , Liang Wu 1 , Suming Chen 1
Chemical Science ( IF 7.6 ) Pub Date : 2020-06-22 , DOI: 10.1039/d0sc01149e Guifang Feng 1 , Yanhong Hao 1 , Liang Wu 1 , Suming Chen 1
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The precise location of C![[double bond, length as m-dash]](https://www.rsc.org/images/entities/char_e001.gif)
C bonds in bioactive molecules is critical for a deep understanding of the relationship between their structures and biological roles. However, the traditional ultraviolet light-based approaches exhibited great limitations. Here, we discovered a new type of visible-light activated [2 + 2] cycloaddition of carbonyl with CC bonds. We found that carbonyl in anthraquinone showed great reactivities towards CC bonds in lipids to form oxetanes under the irradiation of visible-light. Combined with tandem mass spectrometry, this site-specific dissociation of oxetane enabled precisely locating the CC bonds in various kinds of monounsaturated and polyunsaturated lipids. The proof-of-concept applicability of this new type of [2 + 2] photocycloaddition was validated in the global identification of unsaturated lipids in a complex human serum sample. 86 monounsaturated and polyunsaturated lipids were identified with definitive positions of CC bonds, including phospholipids and fatty acids even with up to 6 CC bonds. This study provides new insights into both the photocycloaddition reactions and the structural lipidomics.
中文翻译：
可见光激活的 [2 + 2] 环加成反应能够精确定位脂质中的碳-碳双键
C的精确位置 生物活性分子中的 C 键对于深入理解其结构和生物学作用之间的关系至关重要。然而，传统的基于紫外光的方法表现出很大的局限性。在这里，我们发现了一种新型的可见光激活的羰基与 C 的 [2 + 2] 环加成反应 C 债券。我们发现蒽醌中的羰基对C表现出很强的反应活性 C在可见光照射下与脂质结合形成氧杂环丁烷。结合串联质谱法，氧杂环丁烷的这种位点特异性解离能够精确定位 C 各种单不饱和和多不饱和脂质中的 C 键。这种新型 [2 + 2] 光环加成的概念验证适用性在复杂人血清样品中不饱和脂质的整体鉴定中得到了验证。 86 种单不饱和和多不饱和脂质被确定为 C 的明确位置 C 键，包括磷脂和脂肪酸，甚至具有高达 6 个 C C 债券。这项研究为光环加成反应和结构脂质组学提供了新的见解。
更新日期：2020-07-15
C bonds in bioactive molecules is critical for a deep understanding of the relationship between their structures and biological roles. However, the traditional ultraviolet light-based approaches exhibited great limitations. Here, we discovered a new type of visible-light activated [2 + 2] cycloaddition of carbonyl with CC bonds. We found that carbonyl in anthraquinone showed great reactivities towards CC bonds in lipids to form oxetanes under the irradiation of visible-light. Combined with tandem mass spectrometry, this site-specific dissociation of oxetane enabled precisely locating the CC bonds in various kinds of monounsaturated and polyunsaturated lipids. The proof-of-concept applicability of this new type of [2 + 2] photocycloaddition was validated in the global identification of unsaturated lipids in a complex human serum sample. 86 monounsaturated and polyunsaturated lipids were identified with definitive positions of CC bonds, including phospholipids and fatty acids even with up to 6 CC bonds. This study provides new insights into both the photocycloaddition reactions and the structural lipidomics.
中文翻译：
可见光激活的 [2 + 2] 环加成反应能够精确定位脂质中的碳-碳双键
C的精确位置
生物活性分子中的 C 键对于深入理解其结构和生物学作用之间的关系至关重要。然而，传统的基于紫外光的方法表现出很大的局限性。在这里，我们发现了一种新型的可见光激活的羰基与 C 的 [2 + 2] 环加成反应 C 债券。我们发现蒽醌中的羰基对C表现出很强的反应活性 C在可见光照射下与脂质结合形成氧杂环丁烷。结合串联质谱法，氧杂环丁烷的这种位点特异性解离能够精确定位 C 各种单不饱和和多不饱和脂质中的 C 键。这种新型 [2 + 2] 光环加成的概念验证适用性在复杂人血清样品中不饱和脂质的整体鉴定中得到了验证。 86 种单不饱和和多不饱和脂质被确定为 C 的明确位置 C 键，包括磷脂和脂肪酸，甚至具有高达 6 个 C C 债券。这项研究为光环加成反应和结构脂质组学提供了新的见解。
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