Heterologous expression of a Photorhabdus luminescens syrbactin-like gene cluster results in production of the potent proteasome inhibitor glidobactin A

Amrein, 2004, Functional analysis of genes involved in the synthesis of syringolin A by Pseudomonas syringae pv. syringae B301D-R, Mol Plant-Microbe Interact, 17, 90, 10.1094/MPMI.2004.17.1.90 Ansari, 2004, NRPS-PKS: a knowledge-based resource for analysis of NRPS/PKS megasynthases, Nucleic Acids Res, 32, W405, 10.1093/nar/gkh359 Ausubel, 1987 Christensen, 1999, Molecular tools for the study of biofilm physiology, Methods Enzymol, 20, 10.1016/S0076-6879(99)10004-1 Crawford, 2010, Regulating alternative lifestyles in entomopathogenic bacteria, Curr Biol, 20, 69, 10.1016/j.cub.2009.10.059 Felnagle, 2010, MbtH-like proteins as integral components of bacterial nonribosomal peptide synthetases, Biochemistry, 49, 8815, 10.1021/bi1012854 Groll, 2008, A plant pathogen virulence factor inhibits the eukaryotic proteasome by a novel mechanism, Nature, 452, 755, 10.1038/nature06782 Imker, 2010, N-acylation during glidobactin biosynthesis by the tridomain nonribosomal peptide synthetase module GlbF, Chem Biol, 17, 1077, 10.1016/j.chembiol.2010.08.007 Imker, 2009, SylC catalyzes ureido-bond formation during biosynthesis of the proteasome inhibitor syringolin A, J Am Chem Soc, 131, 18263, 10.1021/ja909170u Krahn, 2011, The chemistry and biology of syringolins, glidobactins and cepafungins (syrbactins), Nat Prod Rep, 28, 1854, 10.1039/c1np00048a Lautru, 2007, MbtH-like protein-mediated cross-talk between non-ribosomal peptide antibiotic and siderophore biosynthetic pathways in Streptomyces coelicolor M145, Microbiology, 153, 1405, 10.1099/mic.0.2006/003145-0 Mo, 1991, Plant signal molecules activate the syrB gene, which is required for syringomycin production by Pseudomonas syringae pv. syringae, J Bacteriol, 173, 5784, 10.1128/jb.173.18.5784-5792.1991 Oka, 1988, Glidobactins A, B and C, new antitumor antibiotics. I. Production, isolation, chemical properties and biological activity, J Antibiot, 41, 1331, 10.7164/antibiotics.41.1331 Oka, 1988, Glidobactins D, E, F, G and H; minor components of the antitumor antibiotic glidobactin, J Antibiot, 41, 1906, 10.7164/antibiotics.41.1906 Prieto, 2012, NRPSsp: non-ribosomal peptide synthase substrate predictor, Bioinformatics, 28, 426, 10.1093/bioinformatics/btr659 Rackham, 2010, Pacidamycin biosynthesis: identification and heterologous expression of the first uridyl peptide antibiotic gene cluster, ChemBioChem, 11, 1700, 10.1002/cbic.201000200 Ramel, 2009, Biosynthesis of the proteasome inhibitor syringolin A: the ureido group joining two amino acids originates from bicarbonate, BMC Biochem, 10, 26, 10.1186/1471-2091-10-26 Schellenberg, 2007, Identification of genes involved in the biosynthesis of the cytotoxic compound glidobactin from a soil bacterium, Environ Microbiol, 9, 1640, 10.1111/j.1462-2920.2007.01278.x Senior, 1976, Enzyme evolution in a microbial community growing on herbicide Dalapon, Nature, 263, 476, 10.1038/263476a0 Staskawicz, 1987, Molecular characterization of cloned avirulence genes from race-0 and race-1 of Pseudomonas syringae pv. glycinea, J Bacteriol, 169, 5789, 10.1128/jb.169.12.5789-5794.1987 Terui, 1990, Structures of cepafungins I, II and III, J Antibiot, 43, 788, 10.7164/antibiotics.43.788 Titus, 1990, Improvement of glidobactin A production by Polyangium brachysporum, J Ind Microbiol, 6, 215, 10.1007/BF01577699 Wäspi, 1998, Syringolin, a novel peptide elicitor from Pseudomonas syringae pv. syringae that induces resistance to Pyricularia oryzae in rice, Mol Plant-Microbe Interact, 11, 727, 10.1094/MPMI.1998.11.8.727 Wäspi, 1999, Identification and structure of a family of syringolin variants: unusual cyclic peptides from Pseudomonas syringae pv. syringae that elicit defense responses in rice, Microbiol Res, 154, 1, 10.1016/S0944-5013(99)80040-8 Wuest, 2011, Enzymatic timing and tailoring of macrolactamization in syringolin biosynthesis, Org Lett, 13, 4518, 10.1021/ol2016687 Zhang, 2010, Activation of the pacidamycin PacL adenylation domain by MbtH-like proteins, Biochemistry, 49, 9946, 10.1021/bi101539b