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Daptomycin is an anionic lipopeptide antibiotic that exhibits antibacterial efficacy and is used clinically to treat gram positive bacterial infections such as MRSA. Daptomycin induces reorganization of cell membranes and alters localization of proteins involved in cell division and cell wall synthesis; this compound also induces release of intracellular Ca2+ and other ions. This compound is also produced by the soil saprotroph Streptomyces roseosporus.
| Cas No. | 103060-53-3 |
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| Purity | ≥97% |
| Formula | C72H101N17O26 |
| Formula Wt. | 1620.67 |
| Chemical Name | N-decanoyl-L-tryptophyl-L-asparaginyl-L-aspartyl-L-threonylglycyl-L-ornithyl-L-aspartyl-D-alanyl-L-aspartylglycyl-D-seryl-threo -3-methyl-L-glutamyl-3-anthraniloyl-L-alanine[egr]1-lactone |
| IUPAC Name | (3S)-3-[[(2S)-4-amino-2-[[(2S)-2-(decanoylamino)-3-(1H-indol-3-yl)propanoyl]amino]-4-oxobutanoyl]amino]-4-[[(3S,6S,9R,15S,18R,21S,24S,30S,31R)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-[(2R)-1-carboxypropan-2-yl]-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonazacyclohentriacont-30-yl]amino]-4-oxobutanoic acid |
| Solubility | Soluble in ethanol (50 mM), methano, DMF, DMSO (100 mM). Slightly soluble in water (25 mg/mL, 5 mM). |
| Appearance | White to off white powder |
| Store Temp | -20°C |
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| Ship Temp | Ambient |
| MSDS | |
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| Info Sheet |
Pogliano J, Pogliano N, Silverman JA. Daptomycin-mediated reorganization of membrane architecture causes mislocalization of essential cell division proteins. J Bacteriol. 2012 Sep;194(17):4494-504. PMID: 22661688.
Vilhena C, Bettencourt A. Daptomycin: a review of properties, clinical use, drug delivery and resistance. Mini Rev Med Chem. 2012 Mar;12(3):202-9. PMID: 22356191
Beiras-Fernandez A, Vogt F, Sodian R, et al. Daptomycin: a novel lipopeptide antibiotic against Gram-positive pathogens. Infect Drug Resist. 2010;3:95-101. PMID: 21694898.