Daptomycin

Isolated from Streptomyces sp. Appearance: Off-white to pale yellow powder. Solubility: Soluble in water (25mg/ml), DMSO (50mg/ml) or methanol (5mg/ml). Identity: Determined by 1H-NMR. InChi Key: DOAKLVKFURWEDJ-RWDRXURGSA-N Smiles: O=C(O[C@H](C)[C@H](NC([C@H](CC(O)=O)NC([C@@H](NC([C@@H](NC(CCCCCCCCC)=O)CC1=CNC2=C1C=CC=C2)=O)CC(N)=O)=O)=O)C(NC3)=O)[C@H](CC(C4=C(N)C=CC=C4)=O)NC([C@@H](NC([C@@H](CO)NC(CNC([C@H](CC(O)=O)NC([C@@H](C)NC([C@H](CC(O)=O)NC([C@@H](NC3=O)CCCN)=O)=O)=O)=O)=O)=O)[C@H](C)CC(O)=O)=O Daptomycin, a naturally occurring cyclic lipopeptide, is a calcium-dependent antibiotic. It exhibits potent bacteriocidal activity against most Gram-positive bacteria in vitro and in vivo, including antibiotic-resistant strains such as MRSA and VRE. Daptomycin disrupts the bacterial plasma membrane function, which results in membrane depolarization consequently leading to inhibition of protein, DNA and RNA synthesis, essential for cell division and cell wall synthesis. Product References In-vitro activity of vancomycin, teicoplanin, daptomycin, ramoplanin, MDL 62873 and other agents against staphylococci, enterococci and Clostridium difficile: A. Bartoloni, et al., J. Antimicrob. Chemother. 26, 627 (1990) Development of daptomycin for Gram-positive infections: F.P. Tally & M.F. DeBruin, J. Antimicrob. Chemother. 46, 523 (2000) Structural transitions as determinants of the action of the calcium-dependent antibiotic daptomycin, D. Jung, et al., Chem. Biol. 11, 949 (2004) Daptomycin: A lipopeptide antibiotic for the treatment of serious Gram-positive infections: J.N. Steenbergen, et al., J. Antimicrob. Chemother. 55, 283 (2005) The action mechanism of daptomycin: S.C. Taylor & M. Palmer, Bioorg. Med. Chem. 24, 6253 (2016) (Review) More Than a Pore: A Current Perspective on the In Vivo Mode of Action of the Lipopeptide Antibiotic Daptomycin: D.A. Gray & M. Wenzel, Antibiotics 9, 17 (2020) (Review) DAPTOMYCIN, its membrane-active mechanism vs. that of other antimicrobial peptides: H.W. Huang, Biochim. Biophys. Acta Biomembr. 1862, 183395 (2020) (Review) The Antibiotic Peptide Daptomycin Functions by Reorganizing the Membrane: A. Pokorny & P.F. Almeida, J. Membr. Biol. 254, 97 (2021) (Review)