Arnison, P. G. et al. Ribosomally synthesized and post-translationally modified peptide natural products: overview and recommendations for a universal nomenclature. Nat. Prod. Rep. 30, 108–160 (2013).
CAS PubMed PubMed Central Article Google Scholar
Tan, N. H. & Zhou, J. Plant cyclopeptides. Chem. Rev. 106, 840–895 (2006).
CAS PubMed Article Google Scholar
Gunasekera, S., Daly, N. L., Anderson, M. A. & Craik, D. J. Chemical synthesis and biosynthesis of the cyclotide family of circular proteins. IUBMB Life 58, 515–524 (2006).
CAS PubMed Article Google Scholar
Cascales, L. & Craik, D. J. Naturally occurring circular proteins: distribution, biosynthesis and evolution. Org. Biomol. Chem. 8, 5035–5047 (2010).
CAS PubMed Article Google Scholar
Lee, J., Mcintosh, J., Hathaway, B. J. & Schmidt, E. W. Using marine natural products to discover a protease that catalyzes peptide macrocyclization of diverse substrates. J. Am. Chem. Soc. 131, 2122–2124 (2009).
CAS PubMed PubMed Central Article Google Scholar
Hegemann, J. D., Zimmermann, M., Xie, X. & Marahiel, M. A. Lasso peptides: an intriguing class of bacterial natural products. Acc. Chem. Res. 48, 1909–1919 (2015).
CAS PubMed Article Google Scholar
Maksimov, M. O. & Link, A. J. Prospecting genomes for lasso peptides. J. Ind. Microbiol. Biotechnol. 41, 333–344 (2014).
CAS PubMed Article Google Scholar
Cheung-Lee, W. L. & Link, A. J. Genome mining for lasso peptides: past, present, and future. J. Ind. Microbiol. Biotechnol. 46, 1371–1379 (2019).
CAS PubMed Article Google Scholar
Kawulka, K. et al. Structure of subtilosin A, an antimicrobial peptide from Bacillus subtilis with unusual posttranslational modifications linking cysteine sulfurs to α-carbons of phenylalanine and threonine. J. Am. Chem. Soc. 125, 4726–4727 (2003).
CAS PubMed Article Google Scholar
Kawulka, K. E. et al. Structure of subtilosin A, a cyclic antimicrobial peptide from Bacillus subtilis with unusual sulfur to α-carbon cross-links: formation and reduction of α-thio-α-amino acid derivatives. Biochemistry 43, 3385–3395 (2004).
CAS PubMed Article Google Scholar
Brown, L. C. W., Acker, M. G., Clardy, J., Walsh, C. T. & Fischbach, M. A. Thirteen posttranslational modifications convert a 14-residue peptide into the antibiotic thiocillin. Proc. Natl Acad. Sci. USA 106, 2549–2553 (2009).
Kelly, W. L., Pan, L. & Li, C. Thiostrepton biosynthesis: prototype for a new family of bacteriocins. J. Am. Chem. Soc. 131, 4327–4334 (2009).
CAS PubMed Article Google Scholar
Bagley, M. C., Dale, J. W., Merritt, E. A. & Xiong, X. Thiopeptide antibiotics. Chem. Rev. 105, 685–714 (2005).
CAS PubMed Article Google Scholar
Willey, J. M. & van der Donk, W. A. Lantibiotics: peptides of diverse structure and function. Annu. Rev. Microbiol. 61, 477–501 (2007).
CAS PubMed Article Google Scholar
Knerr, P. J. & van der Donk, W. A. Discovery, biosynthesis, and engineering of lantipeptides. Annu. Rev. Microbiol. 81, 479–505 (2012).
Bierbaum, G. & Sahl, H. Lantibiotics: mode of action, biosynthesis and bioengineering. Curr. Pharm. Biotechnol. 10, 2–18 (2009).
CAS PubMed Article Google Scholar
Schramma, K. R., Bushin, L. B. & Seyedsayamdost, M. R. Structure and biosynthesis of macrocyclic peptide containing an unprecedented lysine-to-tryptophan crosslink. Nat. Chem. 7, 431–437 (2015).
CAS PubMed PubMed Central Article Google Scholar
Okino, T., Matsuda, H., Murakami, M. & Yamaguchi, K. New microviridins, elastase inhibitors from the blue-green alga Microcystis aeruginosa. Tetrahedron 51, 10679–10686 (1995).
Li, K., Condurso, H. L., Li, G., Ding, Y. & Bruner, S. D. Structural basis for precursor protein-directed ribosomal peptide macrocyclization. Nat. Chem. Biol. 12, 973–979 (2016).
PubMed PubMed Central Article CAS Google Scholar
Liao, R. et al. Thiopeptide biosynthesis featuring ribosomally synthesized precursor peptides and conserved posttranslational modifications. Chem. Biol. 16, 141–147 (2009).
CAS PubMed PubMed Central Article Google Scholar
Walsh, C. T., Malcolmson, S. J. & Young, T. S. Three ring posttranslational circuses: insertion of oxazoles, thiazoles, and pyridines into protein-derived frameworks. ACS Chem. Biol. 7, 429–442 (2012).
CAS PubMed PubMed Central Article Google Scholar
Ireland, C. & Scheuer, P. J. Ulicyclamide and ulithiacyclamide, two new small peptides from a marine tunicate. J. Am. Chem. Soc. 102, 5688 (1980).
Morris, R. P. et al. Ribosomally synthesized thiopeptide antibiotics targeting elongation factor Tu. J. Am. Chem. Soc. 131, 5946–5955 (2009).
CAS PubMed Article Google Scholar
Freeman, M. F. et al. Metagenome mining reveals polytheonamides as posttranslationally modified ribosomal peptides. Science 338, 387–391 (2012).
CAS PubMed Article Google Scholar
Maksimov, M. O., Pan, S. J. & Link, A. J. Lasso peptides: structure, function, biosynthesis, and engineering. Nat. Prod. Rep. 29, 996–1006 (2012).
CAS PubMed Article Google Scholar
Braffman, N. R. et al. Structural mechanism of transcription inhibition by lasso peptides microcin J25 and capistruin. Proc. Natl Acad. Sci. USA 116, 1273–1278 (2019).
CAS PubMed PubMed Central Article Google Scholar
Wilson, K. A. et al. Structure of microcin J25, a peptide inhibitor of bacterial RNA polymerase, is a lassoed tail. J. Am. Chem. Soc. 125, 12475–12483 (2003).
CAS PubMed Article Google Scholar
Travin, D. Y. et al. Structure of ribosome-bound azole-modified peptide phazolicin rationalizes its species-specific mode of bacterial translation inhibition. Nat. Commun. 10, 4563 (2019).
PubMed PubMed Central Article CAS Google Scholar
Metelev, M. et al. Klebsazolicin inhibits 70S ribosome by obstructing the peptide exit tunnel. Nat. Chem. Biol. 13, 1129–1136 (2017).
CAS PubMed PubMed Central Article Google Scholar
Ishitsuka, M. O., Kusumi, T., Kakisawa, H., Kaya, K. & Watanabe, M. M. Microviridin: a novel tricyclic depsipeptide from the toxic cyanobacterium Microcystis viridis. J. Am. Chem. Soc. 112, 8180–8182 (1990).
Ahmed, M. N. et al. Phylogenomic analysis of the microviridin biosynthetic pathway coupled with targeted chemo-enzymatic synthesis yields potent protease inhibitors. ACS Chem. Biol. 12, 1538–1546 (2017).
CAS PubMed Article Google Scholar
Ziemert, N., Ishida, K., Weiz, A., Hertweck, C. & Dittmann, E. Exploiting the natural diversity of microviridin gene clusters for discovery of novel tricyclic depsipeptides. Appl. Environ. Microbiol. 76, 3568–3574 (2010).
CAS PubMed PubMed Central Article Google Scholar
Ziemert, N., Ishida, K., Liaimer, A., Hertweck, C. & Dittmann, E. Ribosomal synthesis of tricyclic depsipeptides in bloom-forming cyanobacteria. Angew. Chem. Int. Ed. 47, 7756–7759 (2008).
Philmus, B., Christiansen, G., Yoshida, W. Y. & Hemscheidt, T. K. Post-translational modification in microviridin biosynthesis. ChemBioChem 9, 3066–3073 (2008).
CAS PubMed Article Google Scholar
Philmus, B., Guerrette, J. P. & Hemscheidt, T. K. Substrate specificity and scope of MvdD, a GRASP-like ligase from the microviridin biosynthetic gene cluster. ACS Chem. Biol. 4, 429–434 (2009).
CAS PubMed Article Google Scholar
Lee, H., Park, Y. & Kim, S. Enzymatic cross-linking of side chains generates a modified peptide with four hairpin-like bicyclic repeats. Biochemistry 56, 4927–4930 (2017).
CAS PubMed Article Google Scholar
Lee, C., Lee, H., Park, J. U. & Kim, S. Introduction of bifunctionality into the multidomain architecture of the ω-ester-containing peptide plesiocin. Biochemistry 59, 285–289 (2020).
CAS PubMed Article Google Scholar
Roh, H., Han, Y., Lee, H. & Kim, S. A topologically distinct modified peptide with multiple bicyclic core motifs expands the diversity of microviridin-like peptides. ChemBioChem 20, 1051–1059 (2019).
CAS PubMed Article Google Scholar
Lee, H., Choi, M., Park, J. U., Roh, H. & Kim, S. Genome mining reveals high topological diversity of ω-ester-containing peptides and divergent evolution of ATP-grasp macrocyclases. J. Am. Chem. Soc. 142, 3013–3023 (2020).
留言 (0)