Light-induced Conversion of Trp to Gly and Gly Hydroperoxide in IgG1

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Issue Date
2013-03-04Author
Haywood, Jessica
Mozziconacci, Olivier
Allegre, Kevin M.
Kerwin, Bruce A.
Schöneich, Christian
Publisher
American Chemical Society
Type
Article
Article Version
Scholarly/refereed, author accepted manuscript
Rights
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Molecular Pharmaceutics, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://doi.org/10.1021/mp1000718.
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Show full item recordAbstract
The exposure of IgG1 in aqueous solution to light with λ = 254 nm or λ > 295 nm yields products consistent with Trp radical cation formation followed by αC-βC cleavage of the Trp side chain. The resulting glycyl radicals are either reduced to Gly, or add oxygen prior to reduction to Gly hydroperoxide. Photoirradiation at λ = 254 nm targets Trp at positions 191 (light chain), 309 and 377 (heavy chain) while photoirradiation at λ > 295 nm targets Trp at position 309 (heavy chain). Mechanistically, the formation of Trp radical cations likely proceeds via photo-induced electron- or hydrogen-transfer to disulfide bonds, yielding thiyl radicals and thiols, where thiols may serve as reductants for the intermediary glycyl or glycylperoxyl radicals.
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Citation
Haywood, J., Mozziconacci, O., Allegre, K. M., Kerwin, B. A., & Schöneich, C. (2013). Light-induced Conversion of Trp to Gly and Gly Hydroperoxide in IgG1. Molecular Pharmaceutics, 10(3), 1146–1150. http://doi.org/10.1021/mp300680c
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