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Issue 44, 2016
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Short protecting-group-free synthesis of 5-acetylsulfanyl-histidines in water: novel precursors of 5-sulfanyl-histidine and its analogues

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Abstract

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.

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

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Publication details

The article was received on 25 Aug 2016, accepted on 11 Oct 2016 and first published on 19 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB01870J
Citation: Org. Biomol. Chem., 2016,14, 10473-10480
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    Short protecting-group-free synthesis of 5-acetylsulfanyl-histidines in water: novel precursors of 5-sulfanyl-histidine and its analogues

    S. Daunay, R. Lebel, L. Farescour, J. Yadan and I. Erdelmeier, Org. Biomol. Chem., 2016, 14, 10473
    DOI: 10.1039/C6OB01870J

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