In Vitro Production of Ergothioneine Isotopologues. (14th January 2021)

• Record Type: Journal Article
• Authors: Beliaeva, Mariia A.; Burn, Reto; Lim, David; Seebeck, Florian P.
• Is Part Of: Angewandte Chemie. Volume 133:Number 10(2021)
• Page Start: 5269
• Page End: 5272
• Publication Date: 2021-01-14
• Subjects: biocatalysis -- ergothioneine -- isotopes -- methyltransferase -- sulfur transferase; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202011096
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Ergothioneine is an emerging component of the redox homeostasis system in human cells and in microbial pathogens, such as Mycobacterium tuberculosis and Burkholderia pseudomallei . The synthesis of stable isotope‐labeled ergothioneine derivatives may provide important tools for deciphering the distribution, function, and metabolism of this compound in vivo. We describe a general protocol for the production of ergothioneine isotopologues with programmable 2 H, 15 N, 13 C, 34 S, and 33 S isotope labeling patterns. This enzyme‐based approach makes efficient use of commercial isotope reagents and is also directly applicable to the synthesis of radio‐isotopologues. Abstract : In an enzyme‐based approach involving commercial isotope reagents, ergothioneine isotopologues with programmable 2 H, 15 N, 13 C, 34 S, and 33 S isotope patterns were synthesized (see scheme). Such isotope‐labeled ergothioneine derivatives are expected to be useful for deciphering the distribution, function, and metabolism of this compound in vivo. The labeling method is directly applicable to the synthesis of radio‐isotopologues.