Mithramycin : Cluster information
Compound
Entry name | Mithramycin |
---|---|
Synonym | Plicamycin |
PKS Type | TypeII |
Starter Unit | acetyl-CoA |
Chain Length | 10 |
Sugar Unit | D-olivose D-mycarose D-oliose |
Classification | Aureolic acid |
Activity | Antibacterial Antitumor |
Composition | C52H76O24 |
Original source
Organism | Streptomyces argillaceus |
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Strain | ATCC 12956 |
Contig | X89899 |
PKS/NRPS Module
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Reference
- Characterization of Streptomyces argillaceus genes encoding a polyketide synthase involved in the biosynthesis of the antitumor mithramycin.
- Lombo F, Blanco G, Fernandez E, Mendez C, Salas JA[PMID: 8654997]Gene. 172 (1996) 87-91
- An ABC transporter is essential for resistance to the antitumor agent mithramycin in the producer Streptomyces argillaceus.
- Fernandez E, Lombo F, Mendez C, Salas JA[PMID: 8757400]Mol Gen Genet. 251 (1996) 692-8
- Cloning and insertional inactivation of Streptomyces argillaceus genes involved in the earliest steps of biosynthesis of the sugar moieties of the antitumor polyketide mithramycin.
- Lombo F, Siems K, Brana AF, Mendez C, Bindseil K, Salas JA[PMID: 9150235]J Bacteriol. 179 (1997) 3354-7
- Identification of two genes from Streptomyces argillaceus encoding glycosyltransferases involved in transfer of a disaccharide during biosynthesis of the antitumor drug mithramycin.
- Fernandez E, Weissbach U, Sanchez Reillo C, Brana AF, Mendez C, Rohr J, Salas JA[PMID: 9733697]J Bacteriol. 180 (1998) 4929-37
- The mithramycin gene cluster of Streptomyces argillaceus contains a positive regulatory gene and two repeated DNA sequences that are located at both ends of the cluster.
- Lombo F, Brana AF, Mendez C, Salas JA[PMID: 9882681]J Bacteriol. 181 (1999) 642-7
- Oxidative cleavage of premithramycin B is one of the last steps in the biosynthesis of the antitumor drug mithramycin.
- Prado L, Fernandez E, Weissbach U, Blanco G, Quiros LM, Brana AF, Mendez C, Rohr J, Salas JA[PMID: 9889148]Chem Biol. 6 (1999) 19-30
- Analysis of two chromosomal regions adjacent to genes for a type II polyketide synthase involved in the biosynthesis of the antitumor polyketide mithramycin in Streptomyces argillaceus.
- Prado L, Lombo F, Brana AF, Mendez C, Rohr J, Salas JA[PMID: 10102355]Mol Gen Genet. 261 (1999) 216-25
- Characterization of two polyketide methyltransferases involved in the biosynthesis of the antitumor drug mithramycin by Streptomyces argillaceus.
- Lozano MJ, Remsing LL, Quiros LM, Brana AF, Fernandez E, Sanchez C, Mendez C, Rohr J, Salas JA[PMID: 10652287]J Biol Chem. 275 (2000) 3065-74
- Characterization of two glycosyltransferases involved in early glycosylation steps during biosynthesis of the antitumor polyketide mithramycin by Streptomyces argillaceus.
- Blanco G, Fernandez E, Fernandez MJ, Brana AF, Weissbach U, Kunzel E, Rohr J, Mendez C, Salas JA[PMID: 10660060]Mol Gen Genet. 262 (2000) 991-1000
- Insertional inactivation of mtrX and mtrY genes from the mithramycin gene cluster affects production and growth of the producer organism Streptomyces argillaceus.
- Garcia-Bernardo J, Brana AF, Mendez C, Salas JA[PMID: 10779713]FEMS Microbiol Lett. 186 (2000) 61-5
- The mtmVUC genes of the mithramycin gene cluster in Streptomyces argillaceus are involved in the biosynthesis of the sugar moieties.
- Gonzalez A, Remsing LL, Lombo F, Fernandez MJ, Prado L, Brana AF, Kunzel E, Rohr J, Mendez C, Salas JA[PMID: 11254130]Mol Gen Genet. 264 (2001) 827-35
- Ketopremithramycins and ketomithramycins, four new aureolic acid-type compounds obtained upon inactivation of two genes involved in the biosynthesis of the deoxysugar moieties of the antitumor drug mithramycin by Streptomyces argillaceus, reveal novel insights into post-PKS tailoring steps of the mithramycin biosynthetic pathway.
- Remsing LL, Garcia-Bernardo J, Gonzalez A, Kunzel E, Rix U, Brana AF, Bearden DW, Mendez C, Salas JA, Rohr J[PMID: 11853433]J Am Chem Soc. 124 (2002) 1606-14
- Mithramycin SK, a novel antitumor drug with improved therapeutic index, mithramycin SA, and demycarosyl-mithramycin SK: three new products generated in the mithramycin producer Streptomyces argillaceus through combinatorial biosynthesis.
- Remsing LL, Gonzalez AM, Nur-e-Alam M, Fernandez-Lozano MJ, Brana AF, Rix U, Oliveira MA, Mendez C, Salas JA, Rohr J[PMID: 12733914]J Am Chem Soc. 125 (2003) 5745-53
- Purification and characterization of a monooxygenase involved in the biosynthetic pathway of the antitumor drug mithramycin.
- Rodriguez D, Quiros LM, Brana AF, Salas JA[PMID: 12813091]J Bacteriol. 185 (2003) 3962-5
- MtmMII-mediated C-methylation during biosynthesis of the antitumor drug mithramycin is essential for biological activity and DNA-drug interaction.
- Rodriguez D, Quiros LM, Salas JA[PMID: 14660589]J Biol Chem. 279 (2004) 8149-58
- Elucidation of the glycosylation sequence of mithramycin biosynthesis: isolation of 3A-deolivosylpremithramycin B and its conversion to premithramycin B by glycosyltransferase MtmGII.
- Nur-e-Alam M, Mendez C, Salas JA, Rohr J[PMID: 15712316]Chembiochem. 6 (2005) 632-6
- Characterization of kinetics and products of the Baeyer-Villiger oxygenase MtmOIV, the key enzyme of the biosynthetic pathway toward the natural product anticancer drug mithramycin from Streptomyces argillaceus.
- Gibson M, Nur-e-alam M, Lipata F, Oliveira MA, Rohr J[PMID: 16351075]J Am Chem Soc. 127 (2005) 17594-5
- Crystallization and X-ray diffraction properties of Baeyer-Villiger monooxygenase MtmOIV from the mithramycin biosynthetic pathway in Streptomyces argillaceus.
- Wang C, Gibson M, Rohr J, Oliveira MA[PMID: 16511225]Acta Crystallogr Sect F Struct Biol Cryst Commun. 61 (2005) 1023-6
- Novel GC-rich DNA-binding compound produced by a genetically engineered mutant of the mithramycin producer Streptomyces argillaceus exhibits improved transcriptional repressor activity: implications for cancer therapy.
- Albertini V, Jain A, Vignati S, Napoli S, Rinaldi A, Kwee I, Nur-e-Alam M, Bergant J, Bertoni F, Carbone GM, Rohr J, Catapano CV[PMID: 16571899]Nucleic Acids Res. 34 (2006) 1721-34
- Premithramycinone G, an early shunt product of the mithramycin biosynthetic pathway accumulated upon inactivation of oxygenase MtmOII.
- Abdelfattah MS, Rohr J[PMID: 16856198]Angew Chem Int Ed Engl. 45 (2006) 5685-9
- Crystal structure of Baeyer-Villiger monooxygenase MtmOIV, the key enzyme of the mithramycin biosynthetic pathway .
- Beam MP, Bosserman MA, Noinaj N, Wehenkel M, Rohr J[PMID: 19364090]Biochemistry. 48 (2009) 4476-87
- Investigating Mithramycin deoxysugar biosynthesis: enzymatic total synthesis of TDP-D-olivose.
- Wang G, Kharel MK, Pahari P, Rohr J[PMID: 21960454]Chembiochem. 12 (2011) 2568-71
- Cooperation of two bifunctional enzymes in the biosynthesis and attachment of deoxysugars of the antitumor antibiotic mithramycin.
- Wang G, Pahari P, Kharel MK, Chen J, Zhu H, Van Lanen SG, Rohr J[PMID: 22997042]Angew Chem Int Ed Engl. 51 (2012) 10638-42
- Structural insight into MtmC, a bifunctional ketoreductase-methyltransferase involved in the assembly of the mithramycin trisaccharide chain.
- Chen JM, Hou C, Wang G, Tsodikov OV, Rohr J[PMID: 25587924]Biochemistry. 54 (2015) 2481-9
- Expanding the Chemical Diversity of the Antitumoral Compound Mithramycin by Combinatorial Biosynthesis and Biocatalysis: The Quest for Mithralogs with Improved Therapeutic Window.
- Mendez C, Gonzalez-Sabin J, Moris F, Salas JA[PMID: 26393942]Planta Med. 81 (2015) 1326-38
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History
- 2016-12-27[Update]
- 2016-01-27[Update]
- 2013-05-28[Release]