Paulomycin B
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| Category | Antibiotics |
| Catalog number | BBF-02376 |
| CAS | 81988-76-3 |
| Molecular Weight | 772.77 |
| Molecular Formula | C33H44N2O17S |
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Description
It is produced by the strain of Str. paulus 273. It has anti-gram-positive bacteria effect, and it has inhibitory effect on staphylococcus aureus resistant to penicillin, streptomycin, neomycin and macrolide antibiotics. The antibacterial activity of Paulomycin A, A1 and B are stronger than other components.
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]-α-L-lyxo-hexopyranosyl]-4-O-[(Z)-2-isothiocyanato-1-oxo-2-buten-1-yl]-β-D-allopyranosyl]-2-amino-5-hydroxy-3,6-dioxo-, (5S)- |
| IUPAC Name | (3S)-3-[(2R,3R,4S,5R,6R)-6-(acetyloxymethyl)-3-hydroxy-4-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyl-5-[(1S)-1-(2-methylpropanoyloxy)ethyl]oxan-2-yl]oxy-5-[(Z)-2-isothiocyanatobut-2-enoyl]oxyoxan-2-yl]-2,3-dihydroxy-6-imino-5-oxocyclohexene-1-carboxylic acid |
| Canonical SMILES | CC=C(C(=O)OC1C(OC(C(C1OC2CC(C(C(O2)C)(C(C)OC(=O)C(C)C)O)OC)O)C3(CC(=O)C(=N)C(=C3O)C(=O)O)O)COC(=O)C)N=C=S |
| InChI | InChI=1S/C33H44N2O17S/c1-8-17(35-12-53)31(43)52-25-19(11-47-16(6)36)50-28(32(44)10-18(37)23(34)22(27(32)39)29(40)41)24(38)26(25)51-21-9-20(46-7)33(45,14(4)48-21)15(5)49-30(42)13(2)3/h8,13-15,19-21,24-26,28,34,38-39,44-45H,9-11H2,1-7H3,(H,40,41)/b17-8-,34-23?/t14-,15-,19+,20-,21-,24+,25+,26-,28+,32+,33-/m0/s1 |
| InChI Key | MXSSKXQZXUFIJA-HDAXSHDCSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 882.3°C at 760 mmHg |
| Melting Point | 105-143°C (dec.) |
| Density | 1.51 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. New insights into paulomycin biosynthesis pathway in Streptomyces albus J1074 and generation of novel derivatives by combinatorial biosynthesis
Aránzazu González, Miriam Rodríguez, Alfredo F Braña, Carmen Méndez, José A Salas, Carlos Olano Microb Cell Fact. 2016 Mar 21;15:56. doi: 10.1186/s12934-016-0452-4.
Background: Streptomyces albus J1074 produces glycosylated antibiotics paulomycin A, B and E that derive from chorismate and contain an isothiocyanate residue in form of paulic acid. Paulomycins biosynthesis pathway involves two glycosyltransferases, three acyltransferases, enzymes required for paulic acid biosynthesis (in particular an aminotransferase and a sulfotransferase), and enzymes involved in the biosynthesis of two deoxysugar moieties: D-allose and L-paulomycose. Results: Inactivation of genes encoding enzymes involved in deoxysugar biosynthesis, paulic acid biosynthesis, deoxysugar transfer, and acyl moieties transfer has allowed the identification of several biosynthetic intermediates and shunt products, derived from paulomycin intermediates, and to propose a refined version of the paulomycin biosynthesis pathway. Furthermore, several novel bioactive derivatives of paulomycins carrying modifications in the L-paulomycose moiety have been generated by combinatorial biosynthesis using different plasmids that direct the biosynthesis of alternative deoxyhexoses. Conclusions: The paulomycins biosynthesis pathway has been defined by inactivation of genes encoding glycosyltransferases, acyltransferases and enzymes involved in paulic acid and L-paulomycose biosynthesis. These experiments have allowed the assignment of each of these genes to specific paulomycin biosynthesis steps based on characterization of products accumulated by the corresponding mutant strains. In addition, novel derivatives of paulomycin A and B containing L-paulomycose modified moieties were generated by combinatorial biosynthesis. The production of such derivatives shows that L-paulomycosyl glycosyltransferase Plm12 possesses a certain degree of flexibility for the transfer of different deoxysugars. In addition, the pyruvate dehydrogenase system form by Plm8 and Plm9 is also flexible to catalyze the attachment of a two-carbon side chain, derived from pyruvate, into both 2,6-dideoxyhexoses and 2,3,6-trideoxyhexoses. The activity of the novel paulomycin derivatives carrying modifications in the L-paulomycose moiety is lower than the original compounds pointing to some interesting structure-activity relationships.
2. 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.
3. Characterization of a 3-hydroxyanthranilic acid 6-hydroxylase involved in paulomycin biosynthesis
Yong Ding, Min Wang, Jine Li, Pengwei Li, Zhenyan Guo, Yihua Chen Biochem Biophys Res Commun. 2021 Mar 5;543:8-14. doi: 10.1016/j.bbrc.2021.01.042. Epub 2021 Jan 23.
Paulomycins (PAUs) refer to a group of glycosylated antibiotics with attractive antibacterial activities against Gram-positive bacteria. They contain a special ring A moiety that is prone to dehydrate between C-4 and C-5 to a quinone-type form at acidic condition, which will reduce the antibacterial activities of PAUs significantly. Elucidation of the biosynthetic mechanism of the ring A moiety may facilitate its structure modifications by combinatorial biosynthesis to generate PAU analogues with enhanced bioactivity or stability. Previous studies showed that the ring A moiety is derived from chorismate, which is converted to 3-hydroxyanthranilic acid (3-HAA) by a 2-amino-2-deoxyisochorismate (ADIC) synthase, a 2,3-dihydro-3-hydroxyanthranilic acid (DHHA) synthase, and a DHHA dehydrogenase. Unfortunately, little is known about the conversion process from 3-HAA to the highly decorated ring A moiety of PAUs. In this work, we characterized Pau17 as an unprecedented 3-HAA 6-hydroxylase responsible for the conversion of 3-HAA to 3,6-DHAA by in vivo and in vitro studies, pushing one step forward toward elucidating the biosynthetic mechanism of the ring A moiety of PAUs.
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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 ╳
