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Synlett 2017; 28(02): 143-147
DOI: 10.1055/s-0036-1588677
DOI: 10.1055/s-0036-1588677
synpacts
Using Radical SAM Chemistry to Access Nucleoside-Containing Compounds
Further Information
Publication History
Received: 27 October 2016
Accepted after revision: 24 November 2016
Publication Date:
12 December 2016 (online)
Abstract
The radical S-adenosylmethionine (SAM) enzyme NosL catalyzes the conversion of l-tryptophan (l-Trp) into 3-methyl-2-indolic acid (MIA) in the biosynthesis of the thiopeptide antibiotic nosiheptide, and this reaction is initiated by the 5′-deoxyadenosyl (dAdo)-radical-mediated hydrogen-atom abstraction from the l-Trp amino group. NosL also exhibits diverse promiscuous activities on various l-Trp analogues, and remarkably, the canonical dAdo-radical-mediated hydrogen abstraction can be switched to radical addition reactions by using a substrate analogue containing an olefin moiety. These findings highlight the intriguing chemistry and catalytic versatility of the radical SAM superfamily enzymes, offering a promising strategy to produce nucleoside-containing compounds, which could be of pharmaceutical interest.
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