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Virginiamycin S1 is a macrolide antibiotic commonly used in livestock as a growth promoter; it is also occasionally used to prevent microbial contamination in ethanol fuels. Virginiamycin S1 is an antibacterial that binds 23S rRNA of the bacterial 50S ribosome, inhibiting peptidyl transferase activity. This compound displays insecticidal activity against Leptinotarsa and acaricidal activity against Tetranychus.
| Cas No. | 23152-29-6 |
|---|---|
| Purity | ≥99% |
| Formula | C43H49N7O10 |
| Formula Wt. | 823.89 |
| IUPAC Name | N-(3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentazatricyclo[20.4.0.06,10]hexacosan-15-yl)-3-hydroxypyridine-2-carboxamide |
| Synonym | Virginiamycin factor S, Staphylomycin S, N-((3-Hydroxy-2-pyridinyl)carbonyl)-L-threonyl-D-alpha- aminobutyryl-L-prolyl-N-methyl-L-phenylalanyl-4-oxo-L- pipecoloyl-L-2-phenylglycine rho-lactone, N-(3-Hydroxypicolinoyl)-L-threonyl-D-alpha-aminobutyryl-L- prolyl-N-methyl-L-phenylalanyl-4-oxo-L-pipecoloyl-L-2- phenylglycine rho-lactone |
| Melting Point | 179-186°C |
| Solubility | Soluble in ethanol, methanol, DMSO, Dichloromethane, DMF, and sparingly, in water. |
| Appearance | White Crystal Powder |
| Store Temp | -20°C |
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| Ship Temp | Ambient |
| MSDS | |
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| Info Sheet |
Batista L, Rivera M, Fonseca M, et al. The influence of virginiamycin on digestion and ruminal parameters under feedlot conditions. Transl Anim Sci. 2024 Feb 14:8:txae019. PMID: 38406320.
Compart DM, Carlson AM, Crawford GI, et al. Presence and biological activity of antibiotics used in fuel ethanol and corn co-product production. J Anim Sci. 2013 May;91(5):2395-404. PMID: 23463564.
Qiu Y, Yang F, Liu Z, et al. Determination of virginiamycin M1 and S1 residues in livestock and poultry products by liquid chromatography-tandem mass spectrometry. Se Pu. 2012 May;30(5):463-7. PMID: 22934408.
Champney WS, Tober CL. Specific inhibition of 50S ribosomal subunit formation in Staphylococcus aureus cells by 16-membered macrolide, lincosamide, and streptogramin B antibiotics. Curr Microbiol. 2000 Aug;41(2):126-35. PMID: 10856379.
Prikrylová V, Samoukina GV, Kandybin NV, et al. Pesticidal activity of virginiamycins S1 and M1. Folia Microbiol (Praha). 1992;37(5):386-8. PMID: 1493906.