Erythromycin C
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| Category | Antibiotics |
| Catalog number | BBF-04432 |
| CAS | 1675-02-1 |
| Molecular Weight | 719.90 |
| Molecular Formula | C36H65NO13 |
| Purity | >98% by HPLC |
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Description
A minor co-metabolite of erythromycin produced by saccharopolyspora erythreae. It exhibits a narrow spectrum of antibacterial activity, and it is much less active than erythromycin A and B.
Specification
| Synonyms | 3''-O-Demethylerythromycin A; Erythromycin Impurity 6 |
| Storage | Store at -20°C |
| IUPAC Name | (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-4-[(2R,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-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)O)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O |
| InChI | InChI=1S/C36H65NO13/c1-13-24-36(10,45)29(40)19(4)26(38)17(2)15-35(9,44)31(50-33-27(39)23(37(11)12)14-18(3)46-33)20(5)28(21(6)32(42)48-24)49-25-16-34(8,43)30(41)22(7)47-25/h17-25,27-31,33,39-41,43-45H,13-16H2,1-12H3/t17-,18-,19+,20+,21-,22+,23+,24-,25+,27-,28+,29-,30+,31-,33+,34-,35-,36-/m1/s1 |
| InChI Key | MWFRKHPRXPSWNT-QNPWSHAKSA-N |
| Source | Saccharopolyspora erythraea |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Bacteria |
| Boiling Point | 826.2±65.0°C (Predicted) |
| Melting Point | 121-125°C |
| Density | 1.23±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Another look at erythromycin
J L Straughan S Afr Med J . 1978 Apr 8;53(14):527-30.
The erythromycins are broadly reviewed from a clinical viewpoint. The antimicrobial spectrum, clinical indications, pharmacokinetics and toxicity are dealt with. The usefulness of erythromycin for respiratory tract infections is stressed. New evidence to support bactericidal activity of this antibiotic is noted. There seems little reason to use the potentially hepatotoxic estolate form of erythromycin. The safety of the other forms of this antibiotic available in this country is emphasized.
2. Erythromycin
D C Brittain Med Clin North Am . 1987 Nov;71(6):1147-54. doi: 10.1016/s0025-7125(16)30802-1.
Erythromycin is the only macrolide antibiotic to have gained widespread use in the United States. Introduced in 1952, it rapidly gained a popularity that it enjoys to this day. Numerous other antimicrobial agents have been marketed since that time: Whole new classes of antibiotics, both natural and synthetic, have been discovered, studied, and released for general use. Many of these newer agents boast a broader spectrum of antimicrobial activity, yet erythromycin's place in the clinician's arsenal is unthreatened because erythromycin remains the drug of first choice for a number of pathogens against which the new drugs are inactive. It is one of the safest antibiotics available for use today and when used against susceptible organisms and in indicated clinical situations, its effectiveness is unquestioned.
3. Knocking out of tailoring genes eryK and eryG in an industrial erythromycin-producing strain of Saccharopolyspora erythraea leading to overproduction of erythromycin B, C and D at different conversion ratios
Y Zhuang, J Qian, J Wu, J Chu, W Liu, S Zhang, Q Zhang Lett Appl Microbiol . 2011 Feb;52(2):129-37. doi: 10.1111/j.1472-765X.2010.02973.x.
Aims:To overproduce erythromycin C, B or D and evaluate the effect of disruption of tailoring genes eryK and eryG in an industrial erythromycin producer.Methods and results:The tailoring genes eryG and eryK were inactivated individually or simultaneously by targeted gene disruption in an industrial strain Saccharopolyspora erythraea HL3168 E3, resulting in the overproduction of erythromycin C (2·48 g l(-1) ), B (1·70 g l(-1) ) or D (2·15 g l(-1) ) in the mutant strain QL-G, QL-K or QL-KG, respectively. Analysis of the erythromycin congeners throughout the fermentation indicated that, at the end of fermentation, comparatively large amount of erythromycin D (0·67 g l(-1) ) was accumulated in QL-G, whereas only small amount of erythromycin D (0·10 g l(-1) ) was produced in QL-K.Conclusions:Inactivation of tailoring genes eryG and eryK in the high producer did not affect the biosynthesis of erythromycin. However, erythromycin D could be more efficiently methylated by EryG than be hydroxylated by EryK.Significance and impact of the study:Development of the mutant strains provides a method for the economical large-scale production of potent lead compounds. The information about the accumulation and conversion of erythromycins in the industrial strains may contribute to further improving erythromycin production.
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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 ╳
