Enzymatic [4+2] Cycloadditions in the Biosynthesis of Spirotetramates and Spirotetronates

Auclair, 2000, Lovastatin nonaketide synthase catalyzes an intramolecular Diels–Alder reaction of a substrate analogue, Journal of the American Chemical Society, 122, 11519, 10.1021/ja003216+ Chen, 2008, Genetic modulation of the overexpression of tailoring genes eryK and eryG leading to the improvement of erythromycin A purity and production in Saccharopolyspora erythraea fermentation, Applied and Environmental Microbiology, 74, 1820, 10.1128/AEM.02770-07 Corey, 2002, Catalytic enantioselective Diels–Alder reactions: Methods, mechanistic fundamentals, pathways, and applications, Angewandte Chemie International Edition, 41, 1650, 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO;2-B Ding, 1994, Pyrroindomycins, novel antibiotics produced by Streptomyces rugosporus sp. LL-42D005. I. Isolation and structure determination, The Journal of Antibiotics, 47, 1250, 10.7164/antibiotics.47.1250 Fang, 2008, Cloning and characterization of the tetrocarcin A gene cluster from Micromonospora chalcea NRRL 11289 reveals a highly conserved strategy for tetronate biosynthesis in spirotetronate antibiotics, Journal of Bacteriology, 190, 6014, 10.1128/JB.00533-08 Gottardi, 2011, Abyssomicin biosynthesis: Formation of an unusual polyketide, antibiotic-feeding studies and genetic analysis, Chembiochem, 12, 1401, 10.1002/cbic.201100172 Hashimoto, 2015, Biosynthesis of versipelostatin: Identification of an enzyme-catalyzed [4+2]-cycloaddition required for macrocyclization of spirotetronate-containing polyketides, Journal of the American Chemical Society, 137, 572, 10.1021/ja510711x He, 2012, Quartromicin biosynthesis: Two alternative polyketide chains produced by one polyketide synthase assembly line, Chemistry & Biology, 19, 1313, 10.1016/j.chembiol.2012.07.024 Jia, 2006, Genetic characterization of the chlorothricin gene cluster as a model for spirotetronate antibiotic biosynthesis, Chemistry & Biology, 13, 575, 10.1016/j.chembiol.2006.03.008 Kakule, 2015, Native promoter strategy for high-yielding synthesis and engineering of fungal secondary metabolites, ACS Synthetic Biology, 4, 625, 10.1021/sb500296p Kanchanabanca, 2013, Unusual acetylation–elimination in the formation of tetronate antibiotics, Angewandte Chemie International Edition, 52, 5785, 10.1002/anie.201301680 Kato, 2015, A new enzyme involved in the control of the stereochemistry in the decalin formation during equisetin biosynthesis, Biochemical and Biophysical Research Communications, 460, 210, 10.1016/j.bbrc.2015.03.011 Kelly, 2008, Intramolecular cyclizations of polyketide biosynthesis: Mining for a “Diels-Alderase”?, Organic & Biomolecular Chemistry, 6, 4483, 10.1039/b814552k Kieser, 2000 Kim, 2010, Mechanistic insights on riboflavin synthase inspired by selective binding of the 6,7-dimethyl-8-ribityllumazine exomethylene anion, Journal of the American Chemical Society, 132, 2983, 10.1021/ja908395r Kim, 2011, Enzyme-catalysed [4+2] cycloaddition is a key step in the biosynthesis of spinosyn A, Nature, 473, 109, 10.1038/nature09981 Kim, 2012, Current developments and challenges in the search for a naturally selected Diels-Alderase, Current Opinion in Chemical Biology, 16, 124, 10.1016/j.cbpa.2011.12.017 Kries, 2016, Structural determinants of reductive terpene cyclization in iridoid biosynthesis, Nature Chemical Biology, 12, 6, 10.1038/nchembio.1955 Li, 2008, Characterization of the saframycin A gene cluster from Streptomyces lavendulae NRRL 11002 revealing a nonribosomal peptide synthetase system for assembling the unusual tetrapeptidyl skeleton in an iterative manner, Journal of Bacteriology, 190, 251, 10.1128/JB.00826-07 Li, 2013, Dissecting glycosylation steps in lobophorin biosynthesis implies an iterative glycosyltransferase, Organic Letters, 15, 1374, 10.1021/ol400342e Ma, 2009, Complete reconstitution of a highly reducing iterative polyketide synthase, Science, 326, 589, 10.1126/science.1175602 MacNeil, 1992, Analysis of Streptomyces avermitilis genes required for avermectin biosynthesis utilizing a novel integration vector, Gene, 111, 61, 10.1016/0378-1119(92)90603-M Nicolaou, 2002, The Diels–Alder reaction in total synthesis, Angewandte Chemie International Edition, 41, 1668, 10.1002/1521-3773(20020517)41:10<1668::AID-ANIE1668>3.0.CO;2-Z Oikawa, 1995, Enzymatic activity catalysing exo-selective Diels-Alder reaction in solanapyrone biosynthesis, Journal of the Chemical Society, Chemical Communications, 13, 1321, 10.1039/C39950001321 Oikawa, 2004, Enzymatic catalysis of the Diels–Alder reaction in the biosynthesis of natural products, Natural Product Reports, 21, 321, 10.1039/B305068H Ose, 2003, Insight into a natural Diels–Alder reaction from the structure of macrophomate synthase, Nature, 422, 185, 10.1038/nature01454 Pang, 2016, Cyclization of polyketides and non-ribosomal peptides on and off their assembly lines, Natural Product Reports, 33, 162, 10.1039/C5NP00095E Reeves, 1999, Transcriptional organization of the erythromycin biosynthetic gene cluster of Saccharopolyspora erythraea, Journal of Bacteriology, 181, 7098, 10.1128/JB.181.22.7098-7106.1999 Roy, 2010, I-TASSER: A unified platform for automated protein structure and function prediction, Nature Protocols, 5, 725, 10.1038/nprot.2010.5 Sato, 2015, Involvement of lipocalin-like CghA in decalin-forming stereoselective intramolecular [4+2] cycloaddition, Chembiochem, 16, 2294, 10.1002/cbic.201500386 Singh, 1994, Pyrroindomycins, novel antibiotics produced by Streptomyces rugosporus LL-42D005. II. Biological activities, The Journal of Antibiotics, 47, 1258, 10.7164/antibiotics.47.1258 Sun, 2013, Spiroketal formation and modification in avermectin biosynthesis involves a dual activity of AveC, Journal of the American Chemical Society, 135, 1540, 10.1021/ja311339u Takahashi, 2011, Reveromycin A biosynthesis uses RevG and RevJ for stereospecific spiroacetal formation, Nature Chemical Biology, 7, 461, 10.1038/nchembio.583 Tian, 2015, An enzymatic [4+2] cyclization cascade creates the pentacyclic core of pyrroindomycins, Nature Chemical Biology, 11, 259, 10.1038/nchembio.1769 Wever, 2015, Chemoenzymatic synthesis of thiazolyl peptide natural products featuring an enzyme-catalyzed formal [4+2] cycloaddition, Journal of the American Chemical Society, 137, 3494, 10.1021/jacs.5b00940 Wu, 2012, Insights into pyrroindomycin biosynthesis reveal a uniform paradigm for tetramate/tetronate formation, Journal of the American Chemical Society, 134, 17342, 10.1021/ja304829g Zhang, 2007, Elucidation of the kijanimicin gene cluster: Insights into the biosynthesis of spirotetronate antibiotics and nitrosugars, Journal of the American Chemical Society, 129, 14670, 10.1021/ja0744854