Short protecting-group-free synthesis of 5-acetylsulfanyl-histidines in water: novel precursors of 5-sulfanyl-histidine and its analogues

The discovery of a non-enzymatic oxidative introduction of sulfur to the 5-position of histidine is reported, by activation with bromine or NBS followed by reaction with thioacetic acid forming novel 5-acetylsulfanyl-histidine. Complementing the previously developed regioselective oxidative S-introd...

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Veröffentlicht in:Organic & biomolecular chemistry 2016-01, Vol.14 (44), p.10473-10480
Hauptverfasser: Daunay, Sylvain, Lebel, Remi, Farescour, Laurence, Yadan, Jean-Claude, Erdelmeier, Irene
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Sprache:eng
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Zusammenfassung:The discovery of a non-enzymatic oxidative introduction of sulfur to the 5-position of histidine is reported, by activation with bromine or NBS followed by reaction with thioacetic acid forming novel 5-acetylsulfanyl-histidine. Complementing the previously developed regioselective oxidative S-introduction to the 2-position of histidine by reaction with cysteine, this surprising finding provides straightforward access in multi-gram quantities to naturally occurring 5-sulfanyl-histidine and its N-methylated analogues, including a hitherto unknown regioisomer of l-ergothioneine.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob01870j