Singlet oxygen oxidation products of biliverdin IX alpha dimethyl ester

Dorazio Sarina J.; Halepas Steven; Bruhn TorstenFleming Kathleen M.Zeller MatthiasBrueckner Christian

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Singlet oxygen oxidation products of biliverdin IX alpha dimethyl ester

机译：Singlet oxygen oxidation products of biliverdin IX alpha dimethyl ester

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Biliverdin IX alpha is a naturally occurring linear tetrapyrrolic product of the enzymatic oxidative ring cleavage of heme. Evidence is mounting that biliverdin possesses antioxidant properties in mammals but its mode of action is unclear. We present the single crystal X-ray structure analysis of two regioisomeric biladien-1,19-diones-ab that are derived from biliverdin IX alpha dimethyl ester by addition of two vicinal trans-methoxy groups to the 4,5- or 15,16-double bonds, respectively. The compounds were likely formed by photosensitized singlet oxygen addition, followed by Lewis acid-catalyzed methanol-induced ring-opening of the intermediate epoxide, and OH-to-OMe substitution. We thus present structural evidence for a possible reaction mechanism by which biliverdin can act as an antioxidant. (c) 2015 Elsevier Ltd. All rights reserved.

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《Bioorganic and medicinal chemistry》 |2015年第24期|7671-7675|共5页
作者
Dorazio Sarina J.; Halepas Steven; Bruhn TorstenFleming Kathleen M.Zeller MatthiasBrueckner Christian;
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作者单位

Univ Connecticut, Dept Chem, Storrs, CT 06269 USA;

Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany;

Youngstown State Univ, Dept Chem, Youngstown, OH 44555 USA;

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正文语种英语
中图分类药学;
关键词
Biliverdin; Antioxidants; Tetrapyrrolic pigments; Reactive oxygen species; Epoxidation;

Singlet oxygen oxidation products of biliverdin IX alpha dimethyl ester

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