Benzindoles

Shagalov, L. B.; Ostapchuk, G. M.; Zlobina, A. D.; Eraksina, V. N.; Babushkina, T. A.; Vasil'ev, A. M.; Ogorodnikova, V. V.; Суворов, Н. Н.

doi:10.1007/bf00673335

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“…TOCYS, ROESY, and HMBC correlations from the indole-H7 to various positions in the Lys side-chain were consistent with cross-links between the C5 and C6 of Trp18 to the αand δpositions of Lys20, respectively (Figure 4b−f, Figures S10 and S11, Table S9). This proposed regiochemistry is consistent with previous work on synthetic 4,5-, 6,7-, and 5,6tetrahydrobenzindoles, 44 with the latter providing the best match to our NMR data. Together, our data indicated that WgkB installs an unprecedented double-cross-linking reaction resulting in a tricyclic tetrahydro [5,6]benzindole modification (Figure 5).…”

Section: ■ Results and Discussionsupporting

confidence: 92%

Charting an Unexplored Streptococcal Biosynthetic Landscape Reveals a Unique Peptide Cyclization Motif

et al. 2018

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Peptide natural products are often used as signals or antibiotics and contain unusual structural modifications, thus providing opportunities for expanding our understanding of Nature's therapeutic and biosynthetic repertoires. Herein, we have investigated the under-explored biosynthetic potential of Streptococci, prevalent bacteria in mammalian microbiomes that include mutualistic, commensal, and pathogenic members. Using a new bioinformatic search strategy, in which we linked the versatile radical Sadenosylmethionine (RaS) enzyme superfamily to an emerging class of natural products in the context of quorum sensing control, we identified numerous, uncharted biosynthetic loci. Focusing on one such locus, we identified an unprecedented posttranslational modification, consisting of a tetrahydro [5,6]benzindole cyclization motif in which four unactivated positions are linked by two C−C bonds in a regio-and stereospecific manner by a single RaS enzyme. Our results expand the scope of reactions that microbes have at their disposal in concocting complex ribosomal peptides.

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Section: ■ Results and Discussionsupporting

confidence: 92%