title: Short protecting-group-free synthesis of 5-acetylsulfanyl-histidines in water: novel precursors of 5-sulfanyl-histidine and its analogues.
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.
authors.affiliation: TETRAHEDRON, 14 Avenue de l'Opéra, 75001 Paris, France. irene.erdelmeier@tetrahedron.fr.
authors.forename: Sylvain
authors.initials: S
authors.lastname: Daunay
authors.affiliation: TETRAHEDRON, 14 Avenue de l'Opéra, 75001 Paris, France. irene.erdelmeier@tetrahedron.fr.
authors.forename: Remi
authors.initials: R
authors.lastname: Lebel
authors.affiliation: TETRAHEDRON, 14 Avenue de l'Opéra, 75001 Paris, France. irene.erdelmeier@tetrahedron.fr.
authors.forename: Laurence
authors.initials: L
authors.lastname: Farescour
authors.affiliation: TETRAHEDRON, 14 Avenue de l'Opéra, 75001 Paris, France. irene.erdelmeier@tetrahedron.fr.
authors.forename: Jean-Claude
authors.initials: JC
authors.lastname: Yadan
authors.affiliation: TETRAHEDRON, 14 Avenue de l'Opéra, 75001 Paris, France. irene.erdelmeier@tetrahedron.fr.
authors.forename: Irene
authors.initials: I
authors.lastname: Erdelmeier
mesh_terms: D060326:Chemistry Techniques, Synthetic; D006639:Histidine / Q000138:chemical synthesis* / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D014867:Water; D006639:Histidine