InChI=1S/C44H48O18/c1-16-9-10-17(2)33(47)28(16)41(53)62-39-21(6)59-27(15-42(39,7)54)60-24-11-12-26(58-20(24)5)61-40-36(50)30(19(4)45)37(51)44(56)38(52)31-22(14-43(40,44)55)18(3)29-32(35(31)49)23(46)13-25(57-8)34(29)48/h9-10,13,20-21,24,26-27,39-40,45,47,49,54-56H,11-12,14-15H2,1-8H3/b30-19+/t20-,21+,24+,26+,27+,39-,40-,42-,43-,44-/m1/s1 |
OWRCRVABZYJUES-FLJLGRLJSA-N |
[H][C@@]1(CC[C@]([H])(O[C@H]2C[C@@](C)(O)[C@H](OC(=O)c3c(C)ccc(C)c3O)[C@H](C)O2)[C@@H](C)O1)O[C@@H]1C(=O)\C(=C(\C)O)C(=O)[C@@]2(O)C(=O)c3c(O)c4C(=O)C=C(OC)C(=O)c4c(C)c3C[C@@]12O |
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Streptomyces sp.
(NCBI:txid1931)
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of strain
MK277 AF1
See:
PubMed
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antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via carbohydrate-containing antibiotic )
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antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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View more via ChEBI Ontology
(2R,3S,6S)-2-methyl-6-{[(1S,3E,4aS,12aR)-4a,6,12a-trihydroxy-3-(1-hydroxyethylidene)-9-methoxy-11-methyl-2,4,5,7,10-pentaoxo-1,2,3,4,4a,5,7,10,12,12a-decahydrotetracen-1-yl]oxy}tetrahydro-2H-pyran-3-yl 2,6-dideoxy-4-O-(2-hydroxy-3,6-dimethylbenzoyl)-3-C-methyl-α-L-xylo-hexopyranoside
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200625-47-4
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CAS Registry Number
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ChemIDplus
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8184047
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Reaxys Registry Number
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Reaxys
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Daum M, Peintner I, Linnenbrink A, Frerich A, Weber M, Paululat T, Bechthold A (2009) Organisation of the biosynthetic gene cluster and tailoring enzymes in the biosynthesis of the tetracyclic quinone glycoside antibiotic polyketomycin. Chembiochem : a European journal of chemical biology 10, 1073-1083 [PubMed:19266534] [show Abstract] Polyketomycin is a tetracyclic quinone glycoside produced by Streptomyces diastatochromogenes Tü6028. It shows cytotoxic and antibiotic activity, in particular against Gram-positive multi-drug-resistant strains (for example, MRSA). The polyketomycin biosynthetic gene cluster has been sequenced and characterised. Its identity was proven by inactivation of a alpha-ketoacyl synthase gene (pokP1) of the "minimal polyketide synthase II" system. In order to obtain valuable information about tailoring steps, we performed further gene-inactivation experiments. The generation of mutants with deletions in oxygenase genes (pokO1, pokO2, both in parallel and pokO4) and methyltransferase genes (pokMT1, pokMT2 and pokMT3) resulted in new polyketomycin derivatives, and provided information about the organisation of the biosynthetic pathway. | Paululat T, Zeeck A, Gutterer JM, Fiedler HP (1999) Biosynthesis of polyketomycin produced by Streptomyces diastatochromogenes Tü 6028. The Journal of antibiotics 52, 96-101 [PubMed:10344562] [show Abstract] The biosynthesis of polyketomycin was investigated by feeding 13C-labeled acetate and propionate to the growing cultures of Streptomyces diastatochromogenes Tü 6028. 13C NMR spectral analysis demonstrated the polyketide origin of the aglycone and the dimethylsalicyloyl moieties. The O-methyl group and 6-CH3 of the aglycone as well as 3B-CH3 of L-axenose and 3C-CH3 of the salicyloyl residue were labeled by feeding L-[methyl-13C]methionine. Both deoxysugars emerged from D-glucose. The biosynthesis of the aglycone and the assembly of the glycoside are discussed. The polyketomycin producing strain may be a candidate for further exploration in combinatorial biosynthesis. | Momose I, Chen W, Nakamura H, Naganawa H, Iinuma H, Takeuchi T (1998) Polyketomycin, a new antibiotic from Streptomyces sp. MK277-AF1. II. Structure determination. The Journal of antibiotics 51, 26-32 [PubMed:9531984] [show Abstract] A new antibiotic, polyketomycin, was isolated from the culture broth of Streptomyces sp. MK277-AF1. The structure was determined by various NMR spectroscopies, X-ray crystallographic analysis and degradation experiments. | Momose I, Chen W, Kinoshita N, Iinuma H, Hamada M, Takeuchi T (1998) Polyketomycin, a new antibiotic from Streptomyces sp. MK277-AF1. I. Taxonomy, production, isolation, physico-chemical properties and biological activities. The Journal of antibiotics 51, 21-25 [PubMed:9531983] [show Abstract] A new antibiotic designated polyketomycin was isolated from the culture broth of Streptomyces sp. MK277-AF1. It was purified by ethyl acetate extraction, Sephadex LH-20 column chromatography and centrifugal partition chromatography (CPC). It inhibited growth of Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA). Its MICs were less than 0.2 microgram/ml. Polyketomycin exhibited cytotoxic activity against nine tumor cell lines at concentrations of 0.9-5.2 micrograms/ml. |
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