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Ramoplanin

Ramoplanin is a peptide antibiotic that displays antibacterial activity against aerobic and anaerobic gram positive bacteria such as Clostridium difficile. Ramoplanin inhibits bacterial growth by binding lipid II and preventing cell wall peptidoglycan formation.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18957441

Cas No.

76168-82-6

Purity

≥96%

Formula

C106H170ClN21O30

Formula Wt.

2254.06

IUPAC Name

2-[[(2R)-2-[[(2S)-2-[[2-[[2-[[(2S,3S)-2-[[2-[[(2R)-5-amino-2-[[(2S)-2-[[(2S,3S)-2-[[(2R)-2-[[(2R)-2-[[(2R,3S)-2-[[(2R)-5-amino-2-[[(2R)-2-[[4-amino-2-[[(2S)-4-amino-2-[[(2Z,4Z)-octa-2,4-dienoyl]amino]-4-oxobutanoyl]amino]-4-oxobutanoyl]amino]-2-(4-hydroxycyclohexyl)acetyl]amino]pentanoyl]amino]-3-hydroxybutanoyl]amino]-2-(4-hydroxycyclohexyl)acetyl]amino]-2-(4-hydroxycyclohexyl)acetyl]amino]-3-hydroxybutanoyl]amino]-3-phenylpropanoyl]amino]pentanoyl]amino]-2-(4-hydroxycyclohexyl)acetyl]amino]-3-hydroxybutanoyl]amino]-2-(4-hydroxycyclohexyl)acetyl]amino]acetyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-2-(3-chloro-4-hydroxycyclohexyl)acetic acid

Appearance

White to off white powder

Mathur H, OConnor PM, Hill C, et al. Analysis of anti-Clostridium difficile activity of thuricin CD, vancomycin, metronidazole, ramoplanin, and actagardine, both singly and in paired combinations. Antimicrob Agents Chemother. 2013 Jun;57(6):2882-6. PMID: 23571539.

Fulco P, Wenzel RP. Ramoplanin: a topical lipoglycodepsipeptide antibacterial agent. Expert Rev Anti Infect Ther. 2006 Dec;4(6):939-45. PMID: 17181409.

Farver DK, Hedge DD, Lee SC. Ramoplanin: a lipoglycodepsipeptide antibiotic. Ann Pharmacother. 2005 May;39(5):863-8. PMID: 15784805.

Hu Y, Helm JS, Chen L, et al. Ramoplanin inhibits bacterial transglycosylases by binding as a dimer to lipid II. J Am Chem Soc. 2003 Jul 23;125(29):8736-7. PMID: 12862463.

ZM-241386