Erythromycin A
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| Category | Antibiotics |
| Catalog number | BBF-01703 |
| CAS | 114-07-8 |
| Molecular Weight | 733.93 |
| Molecular Formula | C37H67NO13 |
| Purity | >98% |
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Description
Erythromycin A is a group of 14-membered macrolide antibiotics produced by Streptomyces erythreus. Erythromycin A is a macrolide antibiotic that has an antimicrobial spectrum similar to or slightly wider than that of penicillin (IC50=1.5 μg/ml). It has a good effect on fish whitehead and white mouth disease, gill rot disease and kidney disease. Erythromycin can be used as an alternative medicine for animals allergic to penicillin.
Specification
| Synonyms | erythromycin; E-Mycin; Erythrocin |
| Storage | -20°C |
| IUPAC Name | (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione |
| Canonical SMILES | CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O |
| InChI | InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1 |
| InChI Key | ULGZDMOVFRHVEP-RWJQBGPGSA-N |
| Source | Saccharopolyspora erythraea |
Properties
| Appearance | Colorless Crystal |
| Boiling Point | 818.4°C at 760 mmHg |
| Melting Point | 190-193°C |
| Density | 1.2 g/cm3 |
| Solubility | Soluble in Methanol, acetone, chloroform, acetonitrile, ethyl acetate |
| LogP | 3.06 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Erythromycin acts by penetrating the bacterial cell membrane and reversibly binding to the 50 S subunit of bacterial ribosomes or donor site so that binding of tRNA (transfer RNA) to the donor site is blocked. Translocation of peptides from the acceptor site to the donor site is prevented, and subsequent protein synthesis is inhibited. Erythromycin is effective only against actively dividing organisms. |
Reference Reading
1. A novel fluorinated erythromycin antibiotic
Rebecca J. M. Goss* and Hui Hong. Chem. Commun., 2005, 3983–3985
This work focuses on the generation of novel fluorinated erythromycin. Analogues of erythromycin in which the macrolide is fluorinated have been generated synthetically, but to date only one example bearing a fluorine in the alkyl side chain has been made. Propionyl coenzyme A (CoA) is the natural starter unit for erythromycin biosynthesis by Saccharopolyspora erythraea and its incorporation leads to the production of erythromycin A 1 (Fig. 1). The loading module of the erythromycin producing polyketide synthase (PKS) 6-deoxyethronolide B synthase (DEBS) is highly selective for propionyl CoA, though it can also accept acetyl CoA. Two different methods of increasing the breadth of starter unit specificity have been explored. The first method, employed by workers in the United States, involves the generation of a strain in which a genetic block is introduced in the first condensation step of erythromycin biosynthesis, the resultant strain is unable to produce polyketide macrolide unless N-acetylcysteamine (NAC) thioesters of a diketide are administered. There has been a recent report of the application of this method to make 15-fluoro-6-deoxyethronolide B.
2. Erythromycin B: conformational analysis and antibacterial activity
Paul Tyson, Abdolreza Hassanzadeh, Jill Barber*. Med. Chem. Commun., 2011, 2, 331–336
Erythromycin A is more abundant and therefore easier to isolate than erythromycin B. Presumably because of the success of erythromycin A, erythromycin B has been largely neglected by the pharmaceutical industry. Recently, however, we have high-lighted a number of advantages of erythromycin B over erythromycin A. Firstly, it is much more stable to acid, because it is unable to cyclize in a 12,9-direction; erythromycin A undergoes facile formation of the spiro-6,9:12,9-cyclized anhydroerythromycin A, which has little or no antibacterial activity. The 2’-esters of erythromycin B are also much more stable to acid than those of erythromycin A. This finding is potentially important in paediatric medicine, in which 2’-esters serve as pro-drugs.Finally, we have been able to derivatize erythromycin B to give pro-pro-drugs, for example erythromycin B enol ether ethyl succinate (3), which are almost insoluble in the medicine bottle and therefore unable to hydrolyse to yield the vile-tasting erythromycin free base. Compound 3 is activated in two stages, as shown in Scheme 1, to yield erythromycin B.
3. Methods and options for the heterologous production of complex natural products
Haoran Zhang, Brett A. Boghigian, John Armando and Blaine A. Pfeifer*. Nat. Prod. Rep., 2011, 28, 125–151
Having established 6dEB production from either S. coelicolor or S. lividans, there was still the need to convert this polyketide intermediate to full erythromycin. However, as opposed to building upon 6dEB biosynthesis in CH999 (as would be expected given the incorporation of the ermE resistance gene), purified 6dEB produced from CH999 production cultures was exogenously fed to mutants of S. erythraea, allowing subsequent conversion to full erythromycin. Using this strategy, numerous rationally designed 6dEB derivatives were generated using the Streptomyces strains and these analogs were then converted to erythromycin derivatives via converter S. erythraea strains.
Spectrum
LC-MS/MS Spectrum - DI-ESI-Ion Trap , Positive
Experimental Conditions
Instrument Type: DI-ESI-Ion Trap
Ionization Mode: Positive
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
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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 ╳
