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Chemoenzymatic Synthesis of Diverse Thiohydroximates From Glucosinolate-Utilizing Enzymes From Helix Pomatia and Caldicellulosiruptor Saccharolyticus

Chemoenzymatic Synthesis of Diverse Thiohydroximates From Glucosinolate-Utilizing Enzymes From Helix Pomatia and Caldicellulosiruptor Saccharolyticus

Jakub Kopycki, Jürgen Schmidt, Steffen Abel, C Douglas Grubb

Biotechnol Lett. 2011 May;33(5):1039-46.

PMID: 21267762

Abstract:

Thiohydroximates comprise a diverse class of compounds important in both biological and industrial chemistry. Their syntheses are generally limited to simple alkyl and aryl compounds with few stereocenters and a narrow range of functional groups. We hypothesized that sequential action of two recombinant enzymes, a sulfatase from Helix pomatia and a β-O-glucosidase from Caldicellulosiruptor saccharolyticus, on glucosinolates would allow synthesis of thiohydroximates from a structurally broad array of abundant precursors. We report successful synthesis of thiohydroximates of varied chemical classes, including from homochiral compounds of demonstrated biological activity. The chemoenzymatic synthetic route reported here should allow access to many, if not all, of the thiohydroximate core structures of the ~200 known naturally occurring glucosinolates. The enrichment of this group for compounds with possible pharmacological potential is discussed.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP9016175	Sulfatase from Helix pomatia		9016-17-5	Price

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