Mureidomycin A
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| Category | Antibiotics |
| Catalog number | BBF-02564 |
| CAS | 114797-04-5 |
| Molecular Weight | 840.90 |
| Molecular Formula | C38H48N8O12S |
| Purity | 95% |
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Description
Mureidomycin A is an antibiotic produced by Str. flavidovirens SANK 60486. It has anti-Pseudomonas aeruginosa activity.
Specification
| Synonyms | MureidomycinA; 114797-04-5; AC1NQZEO; CHEBI:29632; AM012930; NU002483 |
| IUPAC Name | 2-[[1-[[3-[[2-amino-3-(3-hydroxyphenyl)propanoyl]-methylamino]-1-[[(Z)-[(4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-2-ylidene]methyl]amino]-1-oxobutan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]carbamoylamino]-3-(3-hydroxyphenyl)propanoic acid |
| Canonical SMILES | CC(C(C(=O)NC=C1CC(C(O1)N2C=CC(=O)NC2=O)O)NC(=O)C(CCSC)NC(=O)NC(CC3=CC(=CC=C3)O)C(=O)O)N(C)C(=O)C(CC4=CC(=CC=C4)O)N |
| InChI | InChI=1S/C38H48N8O12S/c1-20(45(2)34(53)26(39)16-21-6-4-8-23(47)14-21)31(33(52)40-19-25-18-29(49)35(58-25)46-12-10-30(50)43-38(46)57)44-32(51)27(11-13-59-3)41-37(56)42-28(36(54)55)17-22-7-5-9-24(48)15-22/h4-10,12,14-15,19-20,26-29,31,35,47-49H,11,13,16-18,39H2,1-3H3,(H,40,52)(H,44,51)(H,54,55)(H2,41,42,56)(H,43,50,57)/b25-19-/t20?,26?,27?,28?,29-,31?,35-/m1/s1 |
| InChI Key | LLINEOOFHRQODR-QQCWUGGYSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1.Modes of action of tunicamycin, liposidomycin B, and mureidomycin A: inhibition of phospho-N-acetylmuramyl-pentapeptide translocase from Escherichia coli.
Brandish PE1, Kimura KI, Inukai M, Southgate R, Lonsdale JT, Bugg TD. Antimicrob Agents Chemother. 1996 Jul;40(7):1640-4.
Using a continuous fluorescence-based enzyme assay, we have characterized the antibacterial agents tumicamycin and liposidomycin B as inhibitors of solubilized Escherichia coli phospho-N-acetylmuramyl-pentapeptide translocase. Tunicamycin exhibited reversible inhibition (Ki = 0.55 +/- 0.1 microM) which was noncompetitive with respect to the lipid acceptor substrate and competitive with respect to the fluorescent substrate analog, dansyl-UDPMurNAc-pentapeptide. Liposidomycin B exhibited slow-binding inhibition (Ki = 80 +/- 15 nM) which was competitive with respect to the lipid acceptor substrate and noncompetitive with respect to dansyl-UDPMurNAc-pentapeptide. These results provide insight into the molecular mechanisms of action of these two classes of nucleoside antibiotics.
2.Synthesis and activity of 5'-uridinyl dipeptide analogues mimicking the amino terminal peptide chain of nucleoside antibiotic mureidomycin A.
Howard NI1, Bugg TD. Bioorg Med Chem. 2003 Jul 17;11(14):3083-99.
A series of 5'-uridinyl dipeptides were synthesised which mimic the amino terminal chain of nucleoside antibiotic mureido omycin A. Aminoacyl-beta-alanyl- and aminoacyl-N-methyl-beta-alanyl- dipeptides were attached either via an ester linkage to the 5'-hydroxyl of uridine, or via an amide linkage to 5'-amino-5'-deoxyuridine. The most active inhibitor of Escherichia coli phospho-MurNAc-pentapeptide translocase (MraY) was 5'-O-(L-Ala-N-methyl-beta-alanyl)-uridine (13l), which also showed 97% enzyme inhibition at 2.35 mM concentration, and showed antibacterial activity at 100 microg/mL concentration against Pseudomonas putida. Both the central N-methyl amide linkage and a 5' uridine ester linkage were required for highest biological activity. Enzyme inhibition was shown to be competitive with Mg(2+). It is proposed that the primary amino terminus of the inhibitor binds in place of the Mg(2+) cofactor at the MraY active site, positioned via a cis-N-methyl amide linkage.
3.Intrinsic resistance of Escherichia coli to mureidomycin A and C due to expression of the multidrug efflux system AcrAB-TolC: comparison with the efflux systems of mureidomycin-susceptible Pseudomonas aeruginosa.
Gotoh N1, Murata T, Ozaki T, Kimura T, Kondo A, Nishino T. J Infect Chemother. 2003 Mar;9(1):101-3.
Intrinsic resistance to mureidomycin is shown in Escherichia coli. This is in contrast to Pseudomonas aeruginosa, which generally displays intrinsic resistance to a variety of antimicrobial agents, but not to mureidomycin. Isogenic efflux system mutants from both species were subjected to antibiotic susceptibility tests. These studies showed that the differences regarding the susceptibility of E. coli and P. aeruginosa to mureidomycin A and C may be explained by the expression of efflux systems that mediate resistance to mureidomycin A and C.
4.Slow binding inhibition of phospho-N-acetylmuramyl-pentapeptide-translocase (Escherichia coli) by mureidomycin A.
Brandish PE1, Burnham MK, Lonsdale JT, Southgate R, Inukai M, Bugg TD. J Biol Chem. 1996 Mar 29;271(13):7609-14.
Enzymes of the membrane cycle of reactions in bacterial peptidoglycan biosynthesis remain as unexploited potential targets for antibacterial agents. The first of these enzymes, phospho-N-acetylmuramyl-pentapeptide-translocase (EC 2.7.8.13), has been overexpresed in Escherichia coli and solubilized from particulate fractions. The work of W.A. Weppner and F.C. Neuhaus ((1977) J. Biol. Chem. 252, 2296-303) has been extended to establish a usable routine fluorescence-based continuous assay for solubilized preparations. This assay has been used in the characterization of the natural product, mureidomycin A as a potent slow binding inhibitor of the enzyme with Ki and Ki* of 36 nM and 2 nM, respectively.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
