Purpuromycin
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| Category | Antibiotics |
| Catalog number | BBF-04342 |
| CAS | 53969-01-0 |
| Molecular Weight | 538.41 |
| Molecular Formula | C26H18O13 |
| Purity | 96% |
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Description
A broad spectrum naphthoquinone antibiotic isolated from actinoplanes ianthinogenes.
Specification
| Synonyms | Hydroxyrubromycin; BRN 1419445; Spiro(benzo(1,2-b:5,4-c)-dipyran-2(3H),2'(3'H)-naphtho(2,3-b)furan)-7-carboxylic acid, 4,5',8',9-tetrahydro-4,4',9',10-tetrahydroxy-7'-methoxy-5',8',9-trioxo-, methyl ester |
| IUPAC Name | methyl 4,4',9',10-tetrahydroxy-7'-methoxy-5',8',9-trioxospiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate |
| Canonical SMILES | COC1=CC(=O)C2=C(C1=O)C(=C3C(=C2O)CC4(O3)CC(C5=C(O4)C(=C6C(=C5)C=C(OC6=O)C(=O)OC)O)O)O |
| InChI | InChI=1S/C26H18O13/c1-35-13-5-11(27)16-17(19(13)30)21(32)23-10(18(16)29)6-26(39-23)7-12(28)9-3-8-4-14(24(33)36-2)37-25(34)15(8)20(31)22(9)38-26/h3-5,12,28-29,31-32H,6-7H2,1-2H3 |
| InChI Key | VGXVKHPGBHVPMW-UHFFFAOYSA-N |
Properties
| Appearance | Red Powder |
| Boiling Point | 927.7°C at 760 mmHg |
| Density | 1.83 g/cm3 |
| Solubility | Highly soluble in Sodium Hydroxide; Slightly soluble in Sodium Carbonate, Acetic Acid, Ethyl Acetate, Dioxane, Chloroform, Acetone |
Reference Reading
1. Effect of the antibiotic purpuromycin on cell-free protein-synthesizing systems
M Zamboni, M Denaro, S Sperti, L Montanaro, M Brigotti, F Rambelli Biochem J . 1989 Apr 1;259(1):307-10. doi: 10.1042/bj2590307.
Purpuromycin, an antibiotic isolated from the culture broth of Actinoplanes ianthinogenes, which is very active against Gram-positive bacteria and fungi, inhibits protein synthesis in both prokaryotic and eukaryotic cell-free systems. The ID50 was 9 microM with the endogenous mRNA-directed rabbit reticulocyte lysate, 17 microM with a poly(U)-directed system from Escherichia coli and 69 microM with a poly(U)-directed system from Artemia salina cysts. Of the three steps of elongation, purpuromycin does not affect the peptidyl-transferase reaction, inhibits the elongation factor 1 (EF-1) dependent binding of phenylalanyl-tRNA and stimulates the GTP-dependent binding of EF-2. When protein synthesis is stopped by the addition of purpuromycin, the nascent peptide chains are found in the puromycin-reactive P site. The results suggest that the mechanism of action of purpuromycin is similar to that of fusidic acid. Both antibiotics would seem to produce a stable guanine nucleotide-ribosome-EF-2 complex which allows one round of translocation but prevents, because of a common or overlapping ribosomal binding site for the two elongation factors, the subsequent EF-1-dependent binding of aminoacyl-tRNA.
2. Investigation of a convergent route to purpuromycin: benzofuran formation vs spiroketalization
Stephen P Waters, Marisa C Kozlowski, Michael W Fennie Org Lett . 2006 Jul 20;8(15):3243-6. doi: 10.1021/ol061112j.
[Structure: see text] A mild and efficient [3+2] nitrile oxide/olefin cycloaddition allows coupling of the highly functionalized naphthalene and isocoumarin hemispheres of purpuromycin. A rationale of the inability of advanced keto alcohols to spirocyclize is presented based upon a systematic examination of the electronic factors present in these systems and suggests that the biosynthesis of purpuromycin does not proceed through open-chain intermediates.
3. A concise synthesis of the naphthalene portion of purpuromycin
Andrew N Lowell, Marisa C Kozlowski, Michael W Fennie J Org Chem . 2008 Mar 7;73(5):1911-8. doi: 10.1021/jo7024114.
A concise synthesis of naphthalene compounds for incorporation into a synthetic sequence for the rubromycin family of natural products is presented. These highly substituted naphthalenes are generated in seven and nine steps, respectively, from 2,4,5-trimethoxybenzaldehyde. Three ring-forming methods were explored and the controlled oxygenation of different positions was investigated to yield differentially substituted/protected systems. Key steps to the final products include a Stobbe condensation to form the ring system and a novel series of regioselective oxidations to introduce the required oxygen functionality. These naphthalene products incorporate orthogonal protecting groups and are suitable for combination with a variety of coupling partners.
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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 ╳
