Probing Exchange Units for Combining Iterative and Linear Fungal Nonribosomal Peptide Synthetases

Beld, 2014, The phosphopantetheinyl transferases: catalysis of a post-translational modification crucial for life, Nat. Prod. Rep., 31, 61, 10.1039/C3NP70054B Belshaw, 1999, Aminoacyl-CoAs as probes of condensation domain selectivity in nonribosomal peptide synthesis, Science, 284, 486, 10.1126/science.284.5413.486 Bloudoff, 2016, Chemical probes allow structural insight into the condensation reaction of nonribosomal peptide synthetases, Cell Chem. Biol., 23, 331, 10.1016/j.chembiol.2016.02.012 Boecker, 2018, Aspergillus niger is a superior expression host for the production of bioactive fungal cyclodepsipeptides, Fungal Biol. Biotechnol., 5, 4, 10.1186/s40694-018-0048-3 Bozhüyük, 2017, De novo design and engineering of non-ribosomal peptide synthetases, Nat. Chem., 10, 275, 10.1038/nchem.2890 Bozhüyük, 2019, Modification and de novo design of non-ribosomal peptide synthetases using specific assembly points within condensation domains, Nat. Chem., 11, 653, 10.1038/s41557-019-0276-z Datsenko, 2000, One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products, Proc. Natl. Acad. Sci. U S A, 97, 6640, 10.1073/pnas.120163297 Drake, 2016, Structures of two distinct conformations of holo-non-ribosomal peptide synthetases, Nature, 529, 235, 10.1038/nature16163 Duerfahrt, 2003, Construction of hybrid peptide synthetases for the production of alpha-l-aspartyl-l-phenylalanine, a precursor for the high-intensity sweetener aspartame, Eur. J. Biochem., 270, 4555, 10.1046/j.1432-1033.2003.03858.x Gao, 2016, Translocation of the thioesterase domain for the redesign of plipastatin synthetase, Sci. Rep., 6, 38467, 10.1038/srep38467 Gao, 2012, Cyclization of fungal nonribosomal peptides by a terminal condensation-like domain, Nat. Chem. Biol., 8, 823, 10.1038/nchembio.1047 Gibson, 2009, Enzymatic assembly of DNA molecules up to several hundred kilobases, Nat. Methods, 6, 343, 10.1038/nmeth.1318 Horsman, 2016, Polyketide synthase and non-ribosomal peptide synthetase thioesterase selectivity: logic gate or a victim of fate?, Nat. Prod. Rep., 33, 183, 10.1039/C4NP00148F Linne, 2000, Control of directionality in nonribosomal peptide synthesis: role of the condensation domain in preventing misinitiation and timing of epimerization, Biochemistry, 39, 10439, 10.1021/bi000768w Matthes, 2012, In vitro chemoenzymatic and in vivo biocatalytic syntheses of new beauvericin analogues, Chem. Commun. (Camb.), 48, 5674, 10.1039/c2cc31669b Meyer, 2016, Biochemical dissection of the natural diversification of microcystin provides lessons for synthetic biology of NRPS, Cell Chem. Biol., 23, 462, 10.1016/j.chembiol.2016.03.011 Mootz, 2000, Construction of hybrid peptide synthetases by module and domain fusions, Proc. Natl. Acad. Sci. U S A, 97, 5848, 10.1073/pnas.100075897 Mootz, 2002, Ways of assembling complex natural products on modular nonribosomal peptide synthetases, ChemBioChem, 3, 490, 10.1002/1439-7633(20020603)3:6<490::AID-CBIC490>3.0.CO;2-N Mootz, 2002, Decreasing the ring size of a cyclic nonribosomal peptide antibiotic by in-frame module deletion in the biosynthetic genes, J. Am. Chem. Soc., 124, 10980, 10.1021/ja027276m Mootz, 2002, Functional characterization of 4′-phosphopantetheinyl transferase genes of bacterial and fungal origin by complementation of Saccharomyces cerevisiae lys5, FEMS Microbiol. Lett., 213, 51 Nguyen, 2006, Combinatorial biosynthesis of novel antibiotics related to daptomycin, Proc. Natl. Acad. Sci. U S A, 103, 17462, 10.1073/pnas.0608589103 Richter, 2014, Engineering of Aspergillus niger for the production of secondary metabolites, Fungal Biol. Biotechnol., 1, 4, 10.1186/s40694-014-0004-9 Samel, 2007, Structural and functional insights into a peptide bond-forming bidomain from a nonribosomal peptide synthetase, Structure, 15, 781, 10.1016/j.str.2007.05.008 Sievers, 2014, Fast, scalable generation of high-quality protein multiple sequence alignments using Clustal Omega, Mol. Syst. Biol., 7, 539, 10.1038/msb.2011.75 Stachelhaus, 1995, Rational design of peptide antibiotics by targeted replacement of bacterial and fungal domains, Science, 269, 69, 10.1126/science.7604280 Steiniger, 2017, Harnessing fungal nonribosomal cyclodepsipeptide synthetases for mechanistic insights and tailored engineering, Chem. Sci., 8, 7834, 10.1039/C7SC03093B Steiniger, 2019, Desymmetrization of cyclodepsipeptides by assembly mode switching of iterative nonribosomal peptide synthetases, ACS Synth. Biol., 8, 661, 10.1021/acssynbio.8b00541 Süssmuth, 2017, Nonribosomal peptide synthesis—principles and prospects, Angew. Chem. Int. Ed., 56, 3770, 10.1002/anie.201609079 Süssmuth, 2011, Fungal cyclooligomerdepsipeptides: from classical biochemistry to combinatorial biosynthesis, Nat. Prod. Rep., 28, 99, 10.1039/C001463J Sy-Cordero, 2012, Revisiting the enniatins: a review of their isolation, biosynthesis, structure determination and biological activities, J. Antibiot., 65, 541, 10.1038/ja.2012.71 Takesako, 1996, Precursor directed biosynthesis of aureobasidins, J. Antibiot., 49, 676, 10.7164/antibiotics.49.676 Tanovic, 2008, Crystal structure of the termination module of a nonribosomal peptide synthetase, Science, 321, 659, 10.1126/science.1159850 Thirlway, 2012, Introduction of a non-natural amino acid into a nonribosomal peptide antibiotic by modification of adenylation domain specificity, Angew. Chem. Int. Ed., 51, 7181, 10.1002/anie.201202043 Yakimov, 2000, Recombinant acylheptapeptide lichenysin: high level of production by Bacillus subtilis cells, J. Mol. Microbiol. Biotechnol., 2, 217 Yu, 2013, Functional dissection and module swapping of fungal cyclooligomer depsipeptide synthetases, Chem. Commun. (Camb.), 49, 6176, 10.1039/c3cc42425a Yu, 2017, Decoding and reprogramming fungal iterative nonribosomal peptide synthetases, Nat. Commun., 8, 15349, 10.1038/ncomms15349 Zobel, 2016, Reprogramming the biosynthesis of cyclodepsipeptide synthetases to obtain new enniatins and beauvericins, ChemBioChem, 17, 283, 10.1002/cbic.201500649