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Light-induced Conversion of Trp to Gly and Gly Hydroperoxide in IgG1
Haywood, Jessica Mozziconacci, Olivier Allegre, Kevin M. Kerwin, Bruce A. Schöneich, Christian
Haywood, Jessica
Mozziconacci, Olivier
Allegre, Kevin M.
Kerwin, Bruce A.
Schöneich, Christian
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Abstract
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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2013-03-04
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American Chemical Society
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Haywood_2013.pdf
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Keywords
Immunoglobulin, IgG1, Tryptophan, Photochemistry, Glycine radical, Hydroperoxide
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