【摘 要】
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Main observation and conclusionrnThe radical S-adenosylmethionine (SAM) enzyme NosL catalyzes the conversion of L-tryptophan (L-Trp,1) to 3-methyl-2-indolic acid(MIA,2),a key intermediate in the biosynthesis of the peptide antibiotic nosiheptide.Previous
【机 构】
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Department of Chemistry,Fudan University,Shanghai 200433,China
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Main observation and conclusionrnThe radical S-adenosylmethionine (SAM) enzyme NosL catalyzes the conversion of L-tryptophan (L-Trp,1) to 3-methyl-2-indolic acid(MIA,2),a key intermediate in the biosynthesis of the peptide antibiotic nosiheptide.Previous study showed that this remarkable recombination reaction starts from the cleavage of the Cα-COO-bond to result in a ·CO2-radical migration.In contrast to the radical SAM tyrosine lyases,NosL appears unable to cleave the Cα-Cβ bond,which is intrinsically more favorable to be cleaved than the Cα-COO-bond.In this study,we investigate the NosL activity with tryptamine (11) and tryptophol (12),two L-Trp analogues lacking a carboxylate moiety.We showed that NosL cleaves the C1-C2 bond of these two substrates to produce 3-methylindole (7),suggesting that the enzyme can still catalyze a β-scission when the carboxyl group of Trp is absent.We also showed the enzyme exhibits a promiscuous activity,initiating the reaction by abstracting hydrogen atoms from two different sites to produce two sets of products.
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