title: Regioselectivity of the oxidative C-S bond formation in ergothioneine and ovothiol biosyntheses.
abstract: Ergothioneine (5) and ovothiol (8) are two novel thiol-containing natural products. Their C-S bonds are formed by oxidative coupling reactions catalyzed by EgtB and OvoA enzymes, respectively. In this work, it was discovered that in addition to catalyzing the oxidative coupling between histidine and cysteine (1 → 6 conversion), OvoA can also catalyze a direct oxidative coupling between hercynine (2) and cysteine (2 → 4 conversion), which can shorten the ergothioneine biosynthetic pathway by two steps.
authors.affiliation: Department of Chemistry, Boston University , Boston, Massachusetts 02215, United States.
authors.forename: Heng
authors.initials: H
authors.lastname: Song
authors.forename: Maureen
authors.initials: M
authors.lastname: Leninger
authors.forename: Norman
authors.initials: N
authors.lastname: Lee
authors.forename: Pinghua
authors.initials: P
authors.lastname: Liu
mesh_terms: D001622:Betaine / Q000031:analogs & derivatives / Q000737:chemistry; D019730:Carbon-Sulfur Ligases / Q000378:metabolism*; D002384:Catalysis; D003545:Cysteine / Q000737:chemistry; D004880:Ergothioneine / Q000096:biosynthesis* / Q000737:chemistry / Q000378:metabolism; D006639:Histidine / Q000031:analogs & derivatives / Q000096:biosynthesis / Q000737:chemistry / Q000378:metabolism; D008762:Methylhistidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D008762:Methylhistidines; D013438:Sulfhydryl Compounds; C050085:ovothiol C; D001622:Betaine; D006639:Histidine; D004880:Ergothioneine; D019730:Carbon-Sulfur Ligases; D003545:Cysteine; C007928:hercynine
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