期刊
BIOORGANIC & MEDICINAL CHEMISTRY
卷 23, 期 24, 页码 7671-7675出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2015.11.012
关键词
Biliverdin; Antioxidants; Tetrapyrrolic pigments; Reactive oxygen species; Epoxidation
资金
- NSF [CHE-1058846, CHE-1465133, CHE-0087210]
- Ohio Board of Regents Grant [CAP-491]
- Youngstown State University
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1465133] Funding Source: National Science Foundation
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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