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• W2264473432 endingPage "3337" @default.
• W2264473432 startingPage "3334" @default.
• W2264473432 abstract "The radical S-adenosyl-l-methionine (SAM) enzyme NosL catalyzes the transformation of l-tryptophan into 3-methyl-2-indolic acid (MIA), which is a key intermediate in the biosynthesis of a clinically interesting antibiotic nosiheptide. NosL catalysis was investigated by using the substrate analogue 2-methyl-3-(indol-3-yl)propanoic acid (MIPA), which can be converted into MIA by NosL. Biochemical assays with different MIPA isotopomers in D2 O and H2 O unambiguously indicated that the 5'-deoxyadenosyl (dAdo)-radical-mediated hydrogen abstraction is from the amino group of l-tryptophan and not a protein residue. Surprisingly, the dAdo-radical-mediated hydrogen abstraction occurs at two different sites of MIPA, thereby partitioning the substrate into different reaction pathways. Together with identification of an α,β-unsaturated ketone shunt product, our study provides valuable mechanistic insight into NosL catalysis and highlights the remarkable catalytic flexibility of radical SAM enzymes." @default.
• W2264473432 created "2016-06-24" @default.
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• W2264473432 date "2016-02-02" @default.
• W2264473432 modified "2023-09-26" @default.
• W2264473432 title "Mechanistic Insights into the Radical<i>S</i>-adenosyl-<scp>l</scp>-methionine Enzyme NosL From a Substrate Analogue and the Shunt Products" @default.
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• W2264473432 doi "https://doi.org/10.1002/anie.201509900" @default.
• W2264473432 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/26837062" @default.
• W2264473432 hasPublicationYear "2016" @default.
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