Mechanism of dioxindolylalanine formation by singlet molecular oxygen-mediated oxidation of tryptophan residues

Mechanism of dioxindolylalanine formation by singlet molecular oxygen-mediated oxidation of tryptophan residues
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DOI:
10.1039/c1pp05181d
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发表时间:
2011-01-01
影响因子:
3.1
通讯作者:
Di Mascio, Paolo
Di Mascio, Paolo
中科院分区:
化学3区
文献类型:
--
作者:
Ronsein, Graziella Eliza;Bof de Oliveira, Mauricio Cesar;Di Mascio, Paolo

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色氨酸的单线态分子氧氧化产生非对映异构体二氧吲哚丙氨酸(dioxindolylalanine, diOia)以及氢过氧化物、醇和羰基化合物。基于同位素标记和质谱/质谱分析的机制研究支持通过二氧乙烷中间体形成diOia。
The singlet molecular oxygen-oxidation of tryptophan generates diastereoisomeric dioxindolylalanine (diOia) along with hydroperoxides, alcohols and carbonyl compounds. Mechanistic investigations based on isotopic labeling and MS/MS analyses support diOia formation through a dioxetane intermediate.