Streptolydigin
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| Category | Antibiotics |
| Catalog number | BBF-03486 |
| CAS | 7229-50-7 |
| Molecular Weight | 600.70 |
| Molecular Formula | C32H44N2O9 |
| Purity | >98% |
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Description
Streptolydigin is a nitrogen-containing and oxygen-containing heterocyclic antibiotic produced by Str. lydicus NRRL 2433. It has anti-gram-positive bacteria and mycobacterial activity.
Specification
| Synonyms | Antibiotic D-45; Portamycin |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-2-[(2S,4E)-4-[(2E,4E,6R)-6-[(1R,3R,4S,5R,8R)-1,4-dimethylspiro[2,9-dioxabicyclo[3.3.1]non-6-ene-8,2'-oxirane]-3-yl]-1-hydroxy-4-methylhepta-2,4-dienylidene]-1-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]-3,5-dioxopyrrolidin-2-yl]-N-methylpropanamide |
| Canonical SMILES | CC1C2C=CC3(CO3)C(O2)(OC1C(C)C=C(C)C=CC(=C4C(=O)C(N(C4=O)C5CCC(C(O5)C)O)C(C)C(=O)NC)O)C |
| InChI | InChI=1S/C32H44N2O9/c1-16(14-17(2)28-18(3)23-12-13-32(15-40-32)31(6,42-23)43-28)8-9-22(36)25-27(37)26(19(4)29(38)33-7)34(30(25)39)24-11-10-21(35)20(5)41-24/h8-9,12-14,17-21,23-24,26,28,35-36H,10-11,15H2,1-7H3,(H,33,38)/b9-8+,16-14+,25-22+/t17-,18+,19+,20+,21+,23-,24+,26+,28-,31-,32-/m1/s1 |
| InChI Key | KVTPRMVXYZKLIG-NCAOFHFGSA-N |
Properties
| Appearance | Needle Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Boiling Point | 826.6±65.0°C at 760 mmHg |
| Melting Point | 147-148°C |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1.Insights into the roles of exogenous glutamate and proline in improving streptolydigin production of Streptomyces lydicus with metabolomic analysis.
Cheng JS1, Cui SF, Ding MZ, Yuan YJ. J Ind Microbiol Biotechnol. 2013 Nov;40(11):1303-14. doi: 10.1007/s10295-013-1326-y. Epub 2013 Aug 29.
The addition of precursors was one strategy to improve antibiotic production. The exogenous proline and glutamate, as precursors of streptolydigin, could significantly improve the streptolydigin production, but their underlying molecular mechanisms remain unknown. Herein, metabolomic analysis was carried out to explore the metabolic responses of Streptomyces lydicus to the additions of proline and glutamine. The significant differences in the quantified 53 metabolites after adding the exogenous proline and glutamate were enunciated by gas chromatography coupled to time-of-flight mass spectrometry. Among them, the levels of some fatty acids (e.g., dodecanoic acid, octadecanoic acid, hexadecanoic acid) were significantly decreased after adding glutamate and proline, indicating that the inhibition of fatty acid synthesis might be benefit for the accumulation of streptolydigin. Particularly, the dramatic changes of the identified metabolites, which are involved in glycolysis, the tricarboxylic acid cycle, and the amino acid and fatty acid metabolism, revealed that the additions of glutamate and proline possibly caused the metabolic cross-talk in S.
2.Mycobacterium tuberculosis is resistant to streptolydigin.
Speer A1, Rowland JL, Niederweis M. Tuberculosis (Edinb). 2013 Jul;93(4):401-4. doi: 10.1016/j.tube.2013.03.002. Epub 2013 Apr 13.
Drug resistant strains of Mycobacterium tuberculosis (Mtb) undermine tuberculosis (TB) control. Streptolydigin is a broadly effective antibiotic which inhibits RNA polymerase, similarly to rifampicin, a key drug in current TB chemotherapeutic regimens. Due to a vastly improved chemical synthesis streptolydigin and derivatives are being promoted as putative TB drugs. The microplate Alamar Blue assay revealed that Streptococcus salivarius and Mycobacterium smegmatis were susceptible to streptolydigin with minimum inhibitory concentrations (MICs) of 1.6 mg/L and 6.25 mg/L, respectively. By contrast, the MICs of streptolydigin and two derivatives, streptolydiginone and dihydrostreptolydigin, against Mtb were ≥ 100 mg/L demonstrating that Mtb is resistant to streptolydigin in contrast to previous reports. Further, a porin mutant of M. smegmatis is resistant to streptolydigin indicating that porins mediate uptake of streptolydigin across the outer membrane.
3.Metabolic analysis reveals the amino acid responses of Streptomyces lydicus to pitching ratios during improving streptolydigin production.
Cheng JS1, Liang YQ, Ding MZ, Cui SF, Lv XM, Yuan YJ. Appl Microbiol Biotechnol. 2013 Jul;97(13):5943-54. doi: 10.1007/s00253-013-4790-4. Epub 2013 Mar 14.
Pitching ratio has been reported to impact not only on the primary metabolism, but also the secondary metabolism. Comparative metabolomics was used to explore the metabolic responses of Streptomyces lydicus E9 to pitching ratios (1, 10, and 30%, v/v). We identified more than 120 metabolites involved in glycolysis, tricarboxylic acid cycle, and amino acid and secondary metabolism, of which there are significant differences in the quantified 32 metabolites under different pitching ratios by gas chromatography coupled to time-of-flight mass spectrometry. The intracellular levels of most amino acids (e.g., valine, alanine, and isoleucine) declined with the increases of pitching ratios. Especially, the relative abundances of glutamate and proline were not only decreased with the increases of pitching rations, but also had much low level at stages II and III, which might be related to the significant enhancement in streptolydigin of S. lydicus E9 under 30% high pitching ratio.
4.Antibiotic streptolydigin requires noncatalytic Mg2+ for binding to RNA polymerase.
Zorov S1, Yuzenkova Y, Nikiforov V, Severinov K, Zenkin N. Antimicrob Agents Chemother. 2014;58(3):1420-4. doi: 10.1128/AAC.02248-13. Epub 2013 Dec 16.
Multisubunit RNA polymerase, an enzyme that accomplishes transcription in all living organisms, is a potent target for antibiotics. The antibiotic streptolydigin inhibits RNA polymerase by sequestering the active center in a catalytically inactive conformation. Here, we show that binding of streptolydigin to RNA polymerase strictly depends on a noncatalytic magnesium ion which is likely chelated by the aspartate of the bridge helix of the active center. Substitutions of this aspartate may explain different sensitivities of bacterial RNA polymerases to streptolydigin. These results provide the first evidence for the role of noncatalytic magnesium ions in the functioning of RNA polymerase and suggest new routes for the modification of existing and the design of new inhibitors of transcription.
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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 ╳
