Biosynthesis of Macrolactam BE-14106 Involves Two Distinct PKS Systems and Amino Acid Processing Enzymes for Generation of the Aminoacyl Starter Unit
Tài liệu tham khảo
Aron, 2005, Characterization of a new tailoring domain in polyketide biogenesis: the amine transferase domain of MycA in the mycosubtilin gene cluster, J. Am. Chem. Soc., 127, 14986, 10.1021/ja055247g
Bassett, 2004, Cellular response and molecular mechanism of antitumor activity by leinamycin in MiaPaCa human pancreatic cancer cells, Anticancer Drugs, 15, 689, 10.1097/01.cad.0000136886.72917.6f
Bisang, 1999, A chain initiation factor common to both modular and aromatic polyketide synthases, Nature, 401, 502, 10.1038/46829
Borgos, 2006, Effect of glucose limitation and specific mutations in the module 5 enoyl reductase domains in the nystatin and amphotericin polyketide synthases on polyene macrolide biosynthesis, Arch. Microbiol., 185, 165, 10.1007/s00203-005-0083-3
Borgos, 2006, Probing the structure-function relationship of polyene macrolides: engineered biosynthesis of soluble nystatin analogues, J. Med. Chem., 49, 2431, 10.1021/jm050895w
Bredholt, 2008, Actinomycetes from sediments in the Trondheim fjord, Norway: diversity and biological activity, Mar. Drugs, 6, 12, 10.3390/md6010012
Bruheim, 2004, Chemical diversity of polyene macrolides produced by Streptomyces noursei ATCC 11455 and recombinant strain ERD44 with genetically altered polyketide synthase NysC, Antimicrob. Agents Chemother., 48, 4120, 10.1128/AAC.48.11.4120-4129.2004
Chen, 2001, Aminoacyl-S-enzyme intermediates in β-hydroxylations and α,β-desaturations of amino acids in peptide antibiotics, Biochemistry, 40, 11651, 10.1021/bi0115434
Cheng, 2003, Type I polyketide synthase requiring a discrete acyltransferase for polyketide biosynthesis, Proc. Natl. Acad. Sci. USA, 100, 3149, 10.1073/pnas.0537286100
Duitman, 1999, The mycosubtilin synthetase of Bacillus subtilis ATCC6633: a multifunctional hybrid between a peptide synthetase, an amino transferase, and a fatty acid synthase, Proc. Natl. Acad. Sci. USA, 96, 13294, 10.1073/pnas.96.23.13294
Futamura, 2008, Discovery of incednine as a potent modulator of the anti-apoptotic function of Bcl-xL from microbial origin, J. Am. Chem. Soc., 130, 1822, 10.1021/ja710124p
Gatto, 2005, Elucidating the substrate specificity and condensation domain activity of FkbP, the FK520 pipecolate-incorporating enzyme, Biochemistry, 44, 5993, 10.1021/bi050230w
Hara, 1989, Leinamycin, a new antitumor antibiotic from Streptomyces: producing organism, fermentation and isolation, J. Antibiot. (Tokyo), 42, 1768, 10.7164/antibiotics.42.1768
Hara, 1989, DC 107, a novel antitumor antibiotic produced by a Streptomyces sp, J. Antibiot. (Tokyo), 42, 333, 10.7164/antibiotics.42.333
He, 2008, The LuxR family members GdmRI and GdmRII are positive regulators of geldanamycin biosynthesis in Streptomyces hygroscopicus 17997, Arch. Microbiol., 189, 501, 10.1007/s00203-007-0346-2
Ishikawa, 1999, FramePlot: a new implementation of the frame analysis for predicting protein-coding regions in bacterial DNA with a high G+C content, FEMS Microbiol. Lett., 174, 251, 10.1111/j.1574-6968.1999.tb13576.x
Jakobi, 1996, Maltophilin: a new antifungal compound produced by Stenotrophomonas maltophilia R3089, J. Antibiot. (Tokyo), 49, 1101, 10.7164/antibiotics.49.1101
Jomon, 1972, A new antibiotic, ikarugamycin, J. Antibiot. (Tokyo), 25, 271, 10.7164/antibiotics.25.271
Jørgensen, 2009, Candicidin biosynthetic gene cluster is widely distributed among Streptomyces spp. isolated from the sediments and the neuston layer in the Trondheim fjord, Appl. Environ. Microbiol., 75, 3296, 10.1128/AEM.02730-08
Kakavas, 1997, Identification and characterization of the niddamycin polyketide synthase genes from Streptomyces caelestis, J. Bacteriol., 179, 7515, 10.1128/jb.179.23.7515-7522.1997
Kanda, 1998, Synthesis and antitumor activity of leinamycin derivatives: modifications of C-8 hydroxy and C-9 keto groups, Bioorg. Med. Chem. Lett., 8, 909, 10.1016/S0960-894X(98)00133-4
Kanda, 1999, Synthesis and antitumor activity of novel thioester derivatives of leinamycin, J. Med. Chem., 42, 1330, 10.1021/jm9900366
Kanda, 2003, Synthesis and antitumor activity of novel C-8 ester derivatives of leinamycin, Bioorg. Med. Chem. Lett., 13, 455, 10.1016/S0960-894X(02)00949-6
Kim, 2002, Biochemical evidence for an editing role of thioesterase II in the biosynthesis of the polyketide pikromycin, J. Biol. Chem., 277, 48028, 10.1074/jbc.M207770200
Kojiri, 1992, A new macrocyclic lactam antibiotic, BE-14106, J. Antibiot. (Tokyo), 45, 868, 10.7164/antibiotics.45.868
Komiyama, 1982, Antitumor activity of a new antitumor antibiotic, stubomycin, J. Antibiot. (Tokyo), 35, 703, 10.7164/antibiotics.35.703
Kopp, 2005, Production of the tubulin destabilizer disorazol in Sorangium cellulosum: biosynthetic machinery and regulatory genes, ChemBioChem, 6, 1277, 10.1002/cbic.200400459
Kuhstoss, 1996, Production of a novel polyketide through the construction of a hybrid polyketide synthase, Gene, 183, 231, 10.1016/S0378-1119(96)00565-3
Long, 2002, Engineering specificity of starter unit selection by the erythromycin-producing polyketide synthase, Mol. Microbiol., 43, 1215, 10.1046/j.1365-2958.2002.02815.x
Marahiel, 1997, Modular peptide synthetases involved in nonribosomal peptide synthesis, Chem. Rev., 97, 2651, 10.1021/cr960029e
Mitchell, 2004, Aureoverticillactam, a novel 22-atom macrocyclic lactam from the marine actinomycete Streptomyces aureoverticillatus, J. Nat. Prod., 67, 1400, 10.1021/np049970g
Naruse, 1991, Fluvirucins A1, A2, B1, B2, B3, B4 and B5, new antibiotics active against influenza A virus. III. The stereochemistry and absolute configuration of fluvirucin A1, J. Antibiot. (Tokyo), 44, 756, 10.7164/antibiotics.44.756
Nowakowski, 2006, A phase I trial of twice-weekly 17-allylamino-demethoxy-geldanamycin in patients with advanced cancer, Clin. Cancer Res., 12, 6087, 10.1158/1078-0432.CCR-06-1015
Ogasawara, 2004, Cloning, sequencing, and functional analysis of the biosynthetic gene cluster of macrolactam antibiotic vicenistatin in Streptomyces halstedii, Chem. Biol., 11, 79
Õmura, 2001, Genome sequence of an industrial microorganism Streptomyces avermitilis: deducing the ability of producing secondary metabolites, Proc. Natl. Acad. Sci. USA, 98, 12215, 10.1073/pnas.211433198
Ortiz de Orué Lucana, 2000, The DNA-binding characteristics of the Streptomyces reticuli regulator FurS depend on the redox state of its cysteine residues, Mol. Gen. Genet., 264, 341, 10.1007/s004380000328
Piel, 2004, Unprecedented diversity of catalytic domains in the first four modules of the putative pederin polyketide synthase, ChemBioChem, 5, 93, 10.1002/cbic.200300782
Rascher, 2003, Cloning and characterization of a gene cluster for geldanamycin production in Streptomyces hygroscopicus NRRL 3602, FEMS Microbiol. Lett., 218, 223, 10.1016/S0378-1097(02)01148-5
Rausch, 2005, Specificity prediction of adenylation domains in nonribosomal peptide synthetases (NRPS) using transductive support vector machines (TSVMs), Nucleic Acids Res., 33, 5799, 10.1093/nar/gki885
Reeves, 2001, Alteration of the substrate specificity of a modular polyketide synthase acyltransferase domain through site-specific mutations, Biochemistry, 40, 15464, 10.1021/bi015864r
Reger, 2007, Biochemical and crystallographic analysis of substrate binding and conformational changes in acetyl-CoA synthetase, Biochemistry, 46, 6536, 10.1021/bi6026506
Sandal, 2001, Establishment of okadaic acid resistant cell clones using a cDNA expression library, Cell Death Differ., 8, 754, 10.1038/sj.cdd.4400873
Sandal, 2002, A novel, extraneuronal role for cyclin-dependent protein kinase 5 (CDK5): modulation of cAMP-induced apoptosis in rat leukemia cells, J. Biol. Chem., 277, 20783, 10.1074/jbc.M112248200
Schwarzer, 2002, Regeneration of misprimed nonribosomal peptide synthetases by type II thioesterases, Proc. Natl. Acad. Sci. USA, 99, 14083, 10.1073/pnas.212382199
Scrutton, 2004, Chemical aspects of amine oxidation by flavoprotein enzymes, Nat. Prod. Rep., 21, 722, 10.1039/b306788m
Sekurova, 2004, In vivo analysis of the regulatory genes in the nystatin biosynthetic gene cluster of Streptomyces noursei ATCC 11455 reveals their differential control over antibiotic biosynthesis, J. Bacteriol., 186, 1345, 10.1128/JB.186.5.1345-1354.2004
Settembre, 2003, Structural and mechanistic studies on ThiO, a glycine oxidase essential for thiamin biosynthesis in Bacillus subtilis, Biochemistry, 42, 2971, 10.1021/bi026916v
Shibata, 1988, Chemical modification of hitachimycin synthesis, antibacterial, cytocidal and in vivo antitumor activities of hitachimycin derivatives, J. Antibiot. (Tokyo), 41, 614, 10.7164/antibiotics.41.614
Shibata, 1989, Chemical modification of hitachimycin. II. Synthesis and antitumor activities of carbonate derivatives, J. Antibiot. (Tokyo), 42, 718, 10.7164/antibiotics.42.718
Shibata, 1989, Chemical modification of hitachimycin. III. Synthesis and antitumor activities of amino acyl derivatives, J. Antibiot. (Tokyo), 42, 1114, 10.7164/antibiotics.42.1114
Shindo, 1993, Vicenistatin, a novel 20-membered macrocyclic lactam antitumor antibiotic, J. Antibiot. (Tokyo), 46, 1076, 10.7164/antibiotics.46.1076
Silakowski, 2001, Novel features in a combined polyketide synthase/non-ribosomal peptide synthetase: the myxalamid biosynthetic gene cluster of the myxobacterium Stigmatella aurantiaca Sga15, Chem. Biol., 8, 59, 10.1016/S1074-5521(00)00056-9
Takahashi, 1997, GT32-B new 20-membered macrocyclic lactam antibiotic, J. Antibiot. (Tokyo), 50, 186, 10.7164/antibiotics.50.186
Takano, 1992, Transcriptional regulation of the redD transcriptional activator gene accounts for growth-phase-dependent production of the antibiotic undecylprodigiosin in Streptomyces coelicolor A3 (2), Mol. Microbiol., 6, 2797, 10.1111/j.1365-2958.1992.tb01459.x
Tang, 2007, Chain initiation in the leinamycin-producing hybrid nonribosomal peptide/polyketide synthetase from Streptomyces atroolivaceus S-140, J. Biol. Chem., 282, 20273, 10.1074/jbc.M702814200
Udwary, 2007, Genome sequencing reveals complex secondary metabolome in the marine actinomycete Salinispora tropica, Proc. Natl. Acad. Sci. USA, 104, 10376, 10.1073/pnas.0700962104
Umezawa, 1981, A new antitumor antibiotic, stubomycin, J. Antibiot. (Tokyo), 34, 259, 10.7164/antibiotics.34.259
Uraji, 2007, Effect of salt on the activity of Streptomyces prolyl aminopeptidase, Biochim. Biophys. Acta, 1774, 1462, 10.1016/j.bbapap.2007.08.022
Waldron, 2001, Cloning and analysis of the spinosad biosynthetic gene cluster of Saccharopolyspora spinosa, Chem. Biol., 8, 487, 10.1016/S1074-5521(01)00029-1
Yu, 2002, The biosynthetic gene cluster of the maytansinoid antitumor agent ansamitocin from Actinosynnema pretiosum, Proc. Natl. Acad. Sci. USA, 99, 7968, 10.1073/pnas.092697199
Zafriri, 1981, Mode of action of Myxococcus xanthus antibiotic TA, Antimicrob. Agents Chemother., 19, 349, 10.1128/AAC.19.2.349