Paulomenol B
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02373 |
| CAS | 97670-28-5 |
| Molecular Weight | 647.62 |
| Molecular Formula | C28H41NO16 |
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Description
It is produced by the strain of Str. paulus 273. It has the effect of anti-gram-positive bacteria including Staphylococcus aureus, streptococcus pyogenes, streptococcus pneumoniae and so on.
Specification
| Synonyms | 1-Cyclohexene-1-carboxylic acid, 5-[6-O-acetyl-3-O-[2,6-dideoxy-3-O-methyl-4-C-[(1S)-1-(2-methyl-1-oxopropoxy)ethyl]-a-L-lyxo-hexopyranosyl]-b-D-allopyranosyl]-2-amino-5-hydroxy-3,6-dioxo-, (5S)-; 4'-De-O-(2-isothiocyano-2-butenoyl)paulomycin B |
| IUPAC Name | (3S)-3-[(2R,3R,4R,5R,6R)-6-(acetyloxymethyl)-3,5-dihydroxy-4-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyl-5-[(1S)-1-(2-methylpropanoyloxy)ethyl]oxan-2-yl]oxyoxan-2-yl]-2,3-dihydroxy-6-imino-5-oxocyclohexene-1-carboxylic acid |
| Canonical SMILES | CC1C(C(CC(O1)OC2C(C(OC(C2O)C3(CC(=O)C(=N)C(=C3O)C(=O)O)O)COC(=O)C)O)OC)(C(C)OC(=O)C(C)C)O |
| InChI | InChI=1S/C28H41NO16/c1-10(2)26(37)43-12(4)28(39)11(3)42-17(7-16(28)40-6)45-22-20(32)15(9-41-13(5)30)44-24(21(22)33)27(38)8-14(31)19(29)18(23(27)34)25(35)36/h10-12,15-17,20-22,24,29,32-34,38-39H,7-9H2,1-6H3,(H,35,36)/t11-,12-,15+,16-,17-,20+,21+,22+,24+,27+,28-/m0/s1 |
| InChI Key | YPQBBJZWKRQORN-GRYNUUMSSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 806.0°C at 760 mmHg |
| Density | 1.47 g/cm3 |
| Solubility | Soluble in Chloroform, Methanol |
Reference Reading
1. O-demethylpaulomycins A and B, U-77,802 and U-77,803, paulomenols A and B, new metabolites produced by Streptomyces paulus
A D Argoudelis, L Baczynskyj, S A Mizsak, F B Shilliday J Antibiot (Tokyo). 1988 Oct;41(10):1316-30. doi: 10.7164/antibiotics.41.1316.
O-Demethylpaulomycin A (C33H44N2O17S), O-demethylpaulomycin B (C32H42N2O17S), paulomenol A (C29H43NO16), paulomenol B (C28H41NO16), and the hydrogen sulfide adducts of paulomycin A (U-77,802, C34H48N2O17S2), and paulomycin B (U-77,803, C33H46N2O17S2) have been isolated from fermentations of Streptomyces paulus strain 273. The structure of these compounds was determined by 1H and 13C NMR and fast atom bombardment mass spectrum spectroscopic techniques and degradative studies. The antibacterial properties of these new metabolites, which are related to paulomycins A and B (J. Antibiotics 35: 285-294, 1982), are briefly discussed.
2. Novel Bioactive Paulomycin Derivatives Produced by Streptomyces albus J1074
Jorge Fernández-De la Hoz, Carmen Méndez, José A Salas, Carlos Olano Molecules. 2017 Oct 18;22(10):1758. doi: 10.3390/molecules22101758.
Four novel paulomycin derivatives have been isolated from S. albus J1074 grown in MFE culture medium. These compounds are structural analogs of antibiotics 273a2α and 273a2β containing a thiazole moiety, probably originated through an intramolecular Michael addition. The novel, thiazole, moiety-containing paulomycins show a lower antibiotic activity than paulomycins A and B against Gram-positive bacteria. However, two of them show an improved activity against Gram-negative bacteria. In addition, the four novel compounds are more stable in culture than paulomycins A and B. Thus, the presence of an N-acetyl-l-cysteine moiety linked to the carbon atom of the paulic acid isothiocyanate moiety, via a thioester bond, and the subsequent intramolecular cyclization of the paulic acid to generate a thiazole heterocycle confer to paulomycins a higher structural stability that otherwise will conduce to paulomycin degradation and into inactive paulomenols.
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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 ╳
