Short protecting-group-free synthesis of 5-acetylsulfanyl-histidines in water: novel precursors of 5-sulfanyl-histidine and its analogues.
| Autor: | Daunay S; TETRAHEDRON, 14 Avenue de l'Opéra, 75001 Paris, France. irene.erdelmeier@tetrahedron.fr., Lebel R; TETRAHEDRON, 14 Avenue de l'Opéra, 75001 Paris, France. irene.erdelmeier@tetrahedron.fr., Farescour L; TETRAHEDRON, 14 Avenue de l'Opéra, 75001 Paris, France. irene.erdelmeier@tetrahedron.fr., Yadan JC; TETRAHEDRON, 14 Avenue de l'Opéra, 75001 Paris, France. irene.erdelmeier@tetrahedron.fr., Erdelmeier I; TETRAHEDRON, 14 Avenue de l'Opéra, 75001 Paris, France. irene.erdelmeier@tetrahedron.fr. |
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| Jazyk: | angličtina |
| Zdroj: | Organic & biomolecular chemistry [Org Biomol Chem] 2016 Nov 08; Vol. 14 (44), pp. 10473-10480. |
| DOI: | 10.1039/c6ob01870j |
| Abstrakt: | 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. |
| Databáze: | MEDLINE |
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