Narasin A
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| Category | Antibiotics |
| Catalog number | BBF-02573 |
| CAS | 55134-13-9 |
| Molecular Weight | 765.02 |
| Molecular Formula | C43H72O11 |
| Purity | >98% by HPLC |
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Description
Narasin A is a polyether antibiotic produced by Str. aureofaciena NRRL 5758. It has anti-gram-positive bacteria, anaerobic bacteria, mycoplasma and coccidia activity, and also has antiviral effect.
Specification
| Related CAS | 58331-17-2 (sodium) |
| Synonyms | narasin; Monteban |
| Storage | -20°C |
| IUPAC Name | (2R)-2-[(2R,3S,5S,6R)-6-[(2S,3S,4S,6R)-6-[(3S,5S,7R,9S,10S,12R,15R)-3-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-15-hydroxy-3,10,12-trimethyl-4,6,8-trioxadispiro[4.1.57.35]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-3,5-dimethyloxan-2-yl]butanoic acid |
| Canonical SMILES | CCC(C1C(CC(C(O1)C(C)C(C(C)C(=O)C(CC)C2C(CC(C3(O2)C=CC(C4(O3)CCC(O4)(C)C5CCC(C(O5)C)(CC)O)O)C)C)O)C)C)C(=O)O |
| InChI | InChI=1S/C43H72O11/c1-12-30(35(46)27(8)34(45)28(9)36-23(4)21-24(5)37(51-36)31(13-2)39(47)48)38-25(6)22-26(7)42(52-38)18-15-32(44)43(54-42)20-19-40(11,53-43)33-16-17-41(49,14-3)29(10)50-33/h15,18,23-34,36-38,44-45,49H,12-14,16-17,19-22H2,1-11H3,(H,47,48)/t23-,24-,25-,26+,27-,28-,29-,30-,31+,32+,33+,34+,36+,37+,38-,40-,41+,42-,43-/m0/s1 |
| InChI Key | VHKXXVVRRDYCIK-CWCPJSEDSA-N |
| Source | Streptomyces aureofaciens |
Properties
| Appearance | Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycoplasma; parasites; viruses |
| Boiling Point | 842.5±65.0°C at 760 mmHg |
| Melting Point | 98-100°C |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1.Stereocontrolled synthesis of C1-C17 fragment of narasin via a free radical-based approach.
Brazeau JF1, Guilbault AA, Kochuparampil J, Mochirian P, Guindon Y. Org Lett. 2010 Jan 1;12(1):36-9. doi: 10.1021/ol902414u.
An efficient synthesis of the C1-C17 western unit of narasin was achieved from (S)-Roche ester. Highlights in our synthesis include the successful exploitation of three stereoselective sequences of Lewis acid mediated reaction followed by free-radical-based hydrogen transfer.
2.The isolation and characterization of narasin, a new polyether antibiotic.
Berg DH, Hamill RL. J Antibiot (Tokyo). 1978 Jan;31(1):1-6.
Narasin is a new polyether antibiotic produced by a strain of Streptomyces aureofaciens. It is purified by organic solvent extraction and silica gel chromatography. Narasin is active in vitro against gram-positive bacteria, anaerobic bacteria, and fungi and is effective in protecting chickens from coccidial infections.
3.Anticoccidial efficacy of narasin in battery cage trials.
Jeffers TK1, Tonkinson LV, Callender ME. Poult Sci. 1988 Jul;67(7):1043-9.
Narasin is a polyether monocarboxylic acid antibiotic produced by Streptomyces aureofaciens. An extensive series of battery cage trials was conducted to evaluate the efficacy of narasin against recent field isolates of the pathogenic species of chicken coccidia. Statistical analyses of the results of these studies revealed that each successive increase in the concentration of narasin produced a significant reduction in the severity of cecal and intestinal lesions when compared with those in infected nonmedicated controls. Increasing the concentration of narasin also produced significant improvements in weight gain and feed efficiency when compared to gain and feed efficiency of infected nonmedicated controls. Maximum weight gain of birds infected with Eimeria tenella alone was obtained at a narasin concentration of 60 ppm, but birds infected with E. tenella plus intestinal species of coccidia, when medicated with 80 ppm narasin had weight gains significantly greater than those of birds medicated with 60 ppm narasin.
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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 ╳
