Unusual Chemistry in the Biosynthesis of the Antibiotic Chondrochlorens
Tài liệu tham khảo
Berner, 2006, Genes and enzymes involved in caffeic acid biosynthesis in the actinomycete Saccharothrix espanaensis, J. Bacteriol., 188, 2666, 10.1128/JB.188.7.2666-2673.2006
Beyer, 1999, Biochim. Biophys. Acta, 1445, 185, 10.1016/S0167-4781(99)00041-X
Bisang, 1999, A chain initiation factor common to both modular and aromatic polyketide synthases, Nature, 401, 502, 10.1038/46829
Bode, 2006, Analysis of myxobacterial secondary metabolism goes molecular, J. Ind. Microbiol. Biotechnol., 33, 577, 10.1007/s10295-006-0082-7
Brady, 2002, New natural product families from an environmental DNA (eDNA) gene cluster, J. Am. Chem. Soc., 124, 9968, 10.1021/ja0268985
Buck, 1987, High-performance liquid chromatographic determination of enantiomeric amino acids and amino alcohols after derivatization with O-phthaldialdehyde and various chiral mercaptans. Application to peptide hydrolysates, J. Chromatogr., 387, 255, 10.1016/S0021-9673(01)94529-7
Büdenbender, 2009, Structure and action of the myxobacterial chondrochloren halogenase CndH: a new variant of FAD-dependent halogenases, J. Mol. Biol., 385, 520, 10.1016/j.jmb.2008.10.057
Chan, 2006, Hydroxymalonyl-acyl carrier protein (ACP) and aminomalonyl-ACP are two additional type I polyketide synthase extender units, Proc. Natl. Acad. Sci. USA, 103, 14349, 10.1073/pnas.0603748103
Donadio, 1992, Organization of the enzymatic domains in the multifunctional polyketide synthase involved in erythromycin formation in Saccharopolyspora erythraea, Gene, 111, 51, 10.1016/0378-1119(92)90602-L
Dong, 2005, Tryptophan 7-halogenase (PrnA) structure suggests a mechanism for regioselective chlorination, Science, 309, 2216, 10.1126/science.1116510
Dorrestein, 2005, Dichlorination of a pyrrolyl-S-carrier protein by FADH2-dependent halogenase PltA during pyoluteorin biosynthesis, Proc. Natl. Acad. Sci. USA, 102, 13843, 10.1073/pnas.0506964102
Dorrestein, 2006, The bifunctional glyceryl transferase/phosphatase OzmB belonging to the HAD superfamily that diverts 1,3-bisphosphoglycerate into polyketide biosynthesis, J. Am. Chem. Soc., 128, 10386, 10.1021/ja0639362
Edwards, 2004, Structure and biosynthesis of the jamaicamides, new mixed polyketide-peptide neurotoxins from the marine cyanobacterium Lyngbya majuscula, Chem. Biol., 11, 817, 10.1016/j.chembiol.2004.03.030
Emmert, 2004, Genetics of zwittermicin A production by Bacillus cereus, Appl. Environ. Microbiol., 70, 104, 10.1128/AEM.70.1.104-113.2004
Eppelmann, 2001, Engineered biosynthesis of the peptide antibiotic bacitracin in the surrogate host Bacillus subtilis, J. Biol. Chem., 276, 34824, 10.1074/jbc.M104456200
Fujimori, 2007, What's new in enzymatic halogenations, Curr. Opin. Chem. Biol., 11, 553, 10.1016/j.cbpa.2007.08.002
Gerth, 2003, Myxobacteria: proficient producers of novel natural products with various biological activities—past and future biotechnological aspects with the focus on the genus Sorangium, J. Biotechnol., 106, 233, 10.1016/j.jbiotec.2003.07.015
Gomez Maqueo Chew, 2007, Bacteriochlorophyllide c C-8(2) and C-12(1) methyltransferases are essential for adaptation to low light in Chlorobaculum tepidum, J. Bacteriol., 189, 6176, 10.1128/JB.00519-07
Gutierrez, 2008, Apratoxin D, a potent cytotoxic cyclodepsipeptide from Papua New Guinea collections of the marine cyanobacteria Lyngbya majuscula and Lyngbya sordida, J. Nat. Prod., 71, 1099, 10.1021/np800121a
Haydock, 1995, Divergent structural motifs correlated with the substrate specificity of (methyl)malonyl-CoA:acylcarrier protein transacylase domains in the modular polyketide synthases, FEBS Lett., 374, 246, 10.1016/0014-5793(95)01119-Y
Haydock, 2005, Organization of the biosynthetic gene cluster for the macrolide concanamycin A in Streptomyces neyagawaensis ATCC 27449, Microbiology, 151, 3161, 10.1099/mic.0.28194-0
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
Jansen, 1999, Antibiotics from gliding bacteria, LXXXIII—the crocacins, novel antifungal and cytotoxic antibiotics from Chondromyces crocatus and Chondromyces pediculatus (myxobacteria): isolation and structure elucidation, Eur. J. Org. Chem., 1085, 10.1002/(SICI)1099-0690(199905)1999:5<1085::AID-EJOC1085>3.0.CO;2-G
Jansen, 2002, The ajudazols A and B, novel isochromanones from Chondromyces crocatus (myxobacteria): isolation and structure elucidation, Eur. J. Org. Chem., 917, 10.1002/1099-0690(200203)2002:5<917::AID-EJOC917>3.0.CO;2-Z
Jansen, 2003, Chondrochloren A and B, new β-amino styrenes from Chondromyces crocatus (myxobacteria), Eur. J. Org. Chem., 2684, 10.1002/ejoc.200200699
Kaneda, 1992, Studies on bottromycins. I. 1H and 13C NMR assignments of bottromycin A2, the main component of the complex, J. Antibiot. (Tokyo), 45, 792, 10.7164/antibiotics.45.792
Keller, 2000, Purification and partial characterization of tryptophan 7-halogenase (PrnA) from Pseudomonas fluorescens, Angew. Chem. Int. Ed. Engl., 39, 2300, 10.1002/1521-3773(20000703)39:13<2300::AID-ANIE2300>3.0.CO;2-I
Kieser, 2000
Kopp, 2007, Macrocyclization strategies in polyketide and nonribosomal peptide biosynthesis, Nat. Prod. Rep., 24, 735, 10.1039/b613652b
Kudo, 2007, Cloning of the pactamycin biosynthetic gene cluster and characterization of a crucial glycosyltransferase prior to a unique cyclopentane ring formation, J. Antibiot. (Tokyo), 60, 492, 10.1038/ja.2007.63
Kunze, 1995, Chondramides A–D, new antifungal and cytostatic depsipeptides from Chondromyces crocatus (myxobacteria). Production, physico-chemical and biological properties, J. Antibiot. (Tokyo), 48, 1262, 10.7164/antibiotics.48.1262
Lin, 2007, Regiospecific chlorination of (S)-β-tyrosyl-S-carrier protein catalyzed by SgcC3 in the biosynthesis of the enediyne antitumor antibiotic C-1027, J. Am. Chem. Soc., 129, 12432, 10.1021/ja072311g
Luesch, 2001, Total structure determination of apratoxin A, a potent novel cytotoxin from the marine cyanobacterium Lyngbya majuscula, J. Am. Chem. Soc., 123, 5418, 10.1021/ja010453j
Mallavadhani, 2006, Three new pentacyclic triterpenes and some flavonoids from the fruits of an Indian Ayurvedic plant Dendrophthoe falcata and their estrogen receptor binding activity, Chem. Pharm. Bull. (Tokyo), 54, 740, 10.1248/cpb.54.740
Marsh, 2004, S-adenosylmethionine radical enzymes, Bioorg. Chem., 32, 326, 10.1016/j.bioorg.2004.06.001
Matthew, 2008, Apratoxin E, a cytotoxic peptolide from a Guamanian collection of the marine cyanobacterium Lyngbya bouillonii, J. Nat. Prod., 71, 1113, 10.1021/np700717s
Mulzer, 2009
Pelzer, 1999, Identification and analysis of the balhimycin biosynthetic gene cluster and its use for manipulating glycopeptide biosynthesis in Amycolatopsis mediterranei DSM5908, Antimicrob. Agents Chemother., 43, 1565, 10.1128/AAC.43.7.1565
Puk, 2004, Biosynthesis of chloro-β-hydroxytyrosine, a nonproteinogenic amino acid of the peptidic backbone of glycopeptide antibiotics, J. Bacteriol., 186, 6093, 10.1128/JB.186.18.6093-6100.2004
Rachid, 2006, Molecular and biochemical studies of chondramide formation—highly cytotoxic natural products from Chondromyces crocatus Cm c5, Chem. Biol., 13, 667, 10.1016/j.chembiol.2006.06.002
Recktenwald, 2002, Nonribosomal biosynthesis of vancomycin-type antibiotics: a heptapeptide backbone and eight peptide synthetase modules, Microbiology, 148, 1105, 10.1099/00221287-148-4-1105
Reichenbach, 2001, Myxobacteria, producers of novel bioactive substances, J. Ind. Microbiol. Biotechnol., 27, 149, 10.1038/sj.jim.7000025
Rose, 2003, CODEHOP (COnsensus-DEgenerate Hybrid Oligonucleotide Primer) PCR primer design, Nucleic Acids Res., 31, 3763, 10.1093/nar/gkg524
Rouhiainen, 2000, Genes encoding synthetases of cyclic depsipeptides, anabaenopeptilides, in Anabaena strain 90, Mol. Microbiol., 37, 156, 10.1046/j.1365-2958.2000.01982.x
Sambrook, 1989
Schneiker, 2007, Complete genome sequence of the myxobacterium Sorangium cellulosum, Nat. Biotechnol., 25, 1281, 10.1038/nbt1354
Schwecke, 1995, The biosynthetic gene cluster for the polyketide immunosuppressant rapamycin, Proc. Natl. Acad. Sci. USA, 92, 7839, 10.1073/pnas.92.17.7839
Shimkets, 1993, The myxobacterial genome, 85
Shyr, 2006, Rossicasins A, B and rosicaside F, three new phenylpropanoid glycosides from Boschniakia rossica, Chem. Pharm. Bull. (Tokyo), 54, 252, 10.1248/cpb.54.252
Silakowski, 1999, New lessons for combinatorial biosynthesis from myxobacteria: the myxothiazol biosynthetic gene cluster of Stigmatella aurantiaca DW4/3-1, J. Biol. Chem., 274, 37391, 10.1074/jbc.274.52.37391
Sosio, 2004, Organization of the teicoplanin gene cluster in Actinoplanes teichomyceticus, Microbiology, 150, 95, 10.1099/mic.0.26507-0
Stachelhaus, 1995, Modular structure of peptide synthetases revealed by dissection of the multifunctional enzyme GrsA, J. Biol. Chem., 270, 6163, 10.1074/jbc.270.11.6163
Staden, 1996, The Staden sequence analysis package, Mol. Biotechnol., 5, 233, 10.1007/BF02900361
Steinmetz, 2007, Thuggacins, macrolide antibiotics active against Mycobacterium tuberculosis: isolation from myxobacteria, structure elucidation, conformation analysis and biosynthesis, Chemistry, 13, 5822, 10.1002/chem.200700269
Tang, 2004, Elucidating the mechanism of cis double bond formation in epothilone biosynthesis, J. Am. Chem. Soc., 126, 46, 10.1021/ja030503f
van Wageningen, 1998, Sequencing and analysis of genes involved in the biosynthesis of a vancomycin group antibiotic, Chem. Biol., 5, 155, 10.1016/S1074-5521(98)90060-6
Walsh, 2007, The chemical versatility of natural-product assembly lines, Acc. Chem. Res., 41, 4, 10.1021/ar7000414
Weissman, 2005, Combinatorial biosynthesis of reduced polyketides, Nat. Rev. Microbiol., 3, 925, 10.1038/nrmicro1287
Wenzel, 2007, Myxobacterial natural product assembly lines: fascinating examples of curious biochemistry, Nat. Prod. Rep., 24, 1211, 10.1039/b706416k
Wenzel, 2006, On the biosynthetic origin of methoxymalonyl-acyl carrier protein, the substrate for incorporation of “glycolate” units into ansamitocin and soraphen A, J. Am. Chem. Soc., 128, 14325, 10.1021/ja064408t
Williamson, 1985, Biosynthesis of the β-lactam antibiotic, thienamycin, by Streptomyces cattleya, J. Biol. Chem., 260, 4637, 10.1016/S0021-9258(18)89118-9
Wu, 2000, The FK520 gene cluster of Streptomyces hygroscopicus var. ascomyceticus (ATCC 14891) contains genes for biosynthesis of unusual polyketide extender units, Gene, 251, 81, 10.1016/S0378-1119(00)00171-2
Yadav, 2003, Computational approach for prediction of domain organization and substrate specificity of modular polyketide synthases, J. Mol. Biol., 328, 335, 10.1016/S0022-2836(03)00232-8
Yeh, 2005, Robust in vitro activity of RebF and RebH, a two-component reductase/halogenase, generating 7-chlorotryptophan during rebeccamycin biosynthesis, Proc. Natl. Acad. Sci. USA, 102, 3960, 10.1073/pnas.0500755102
Yeh, 2007, Chlorination by a long-lived intermediate in the mechanism of flavin-dependent halogenases, Biochemistry, 46, 1284, 10.1021/bi0621213
Zehner, 2005, A regioselective tryptophan 5-halogenase is involved in pyrroindomycin biosynthesis in Streptomyces rugosporus LL-42D005, Chem. Biol., 12, 445, 10.1016/j.chembiol.2005.02.005