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AdipoGen Life Sciences

Ramoplanin A2

CHF 45.00
In stock
AG-CN2-0318-M0011 mgCHF 45.00
AG-CN2-0318-M0055 mgCHF 135.00
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Product Details
Synonyms Antibiotic A16686A2; MDL-62198; Antibiotic A 16686
Product Type Chemical
Properties
Formula

C119H154ClN21O40
MW 2554.1
CAS 81988-88-7 [A2]
Source/Host Chemicals Isolated from Actinoplanes sp.
Purity Chemicals ≥90% (HPLC)
Appearance White to off-white powder.
Solubility Soluble in DMSO or water.
Identity Determined by 1H-NMR and MS.
Other Product Data

Purity Note: The purity is referred exclusively to the main congener(s), the sample also contains minor related congeners. See: Ramoplanin (A-16686), a new glycolipodepsipeptide antibiotic. III. Structure elucidation: R. Ciabatti, et al.; J. Antibiot. 42, 254 (1989)
InChi Key KGZHFKDNSAEOJX-BALZYLSASA-N
Smiles OC[C@H]([C@@H](O)[C@H](O)[C@@H]1O)O[C@]1([H])O[C@@H]2[C@H](O[C@H](CO)[C@@H](O)[C@@H]2O)OC3=CC=C([C@@H]4NC([C@H](NC([C@@H](NC(C(NC([C@@H](C5=CC=C(O)C=C5)NC([C@@](C6=CC=C(O)C=C6)([H])NC([C@@](NC([C@H](NC([C@@H](C7=CC=C(O)C=C7)NC([C@@H](NC([C@H](CC(N)=O)NC(/C=C\C=C\CC(C)C)=O)=O)[C@@H](C(N)=O)OC([C@@](C8=CC(Cl)=C(O)C=C8)([H])NC([C@@H](C)NC([C@H](CC(C)C)NC(CNC([C@H](C9=CC=C(O)C=C9)NC([C@]([C@H](O)C)([H])NC4=O)=O)=O)=O)=O)=O)=O)=O)=O)CCCN)=O)([H])[C@H](O)C)=O)=O)=O)[C@@H](O)C)=O)CC%10=CC=CC=C%10)=O)CCCN)=O)C=C3
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Protect from light.
Protect from light when in solution.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
Description

  • Glycolipodepsipeptide antibiotic. 

  • Complex of structurally related molecules A1, A2 and A3, with ramoplanin A2 as the primary component. 

  • Antibacterial and antiviral agent with activity against aerobic and anaerobic Gram-positive bacteria such as Clostridium difficile and antibiotic-resistant enterococci.

  • Inhibits cell wall synthesis and consequently bacterial growth by forming a complex with lipid intermediate II (Lipid II), a key intermediate in peptidoglycan biosynthesis.

Product References

  1. A-16686, a new antibiotic from Actinoplanes. I. Fermentation, isolation and preliminary physico-chemical characteristics: B. Cavalleri, et al.; J. Antibiot. 37, 309 (1984)

  2. A-16686, a new antibiotic from Actinoplanes. II. Biological properties: R. Pallanza, et al.; J. Antibiot. 37, 318 (1984)

  3. In vitro evaluation of ramoplanin (MDL 62198, A 16686): S. Dixson, et al.; Eur. J. Clin. Microbiol. Infect. Dis. 7, 819 (1988)

  4. In vitro bactericidal activity of the glycopeptide compounds vancomycin, teicoplanin and ramoplanin (A-16686/MDL 62,198): M.D. O'Hare, et al.; J. Chemother. 1, 210 (1989)

  5. In-vitro studies with ramoplanin (MDL 62,198): a novel lipoglycopeptide antimicrobial: M.D. O'Hare, et al.; J. Antimicrob. Chemother. 25, 217 (1990)

  6. Inhibition of peptidoglycan biosynthesis by ramoplanin: E.A. Somner & P.E. Reynolds; Antimicrob. Agents Chemother. 34, 413 (1990)

  7. 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)

  8. Bactericidal activity of ramoplanin against antibiotic-resistant enterococci: C.C. Johnson, et al.; Antimicrob. Agents Chemother. 36, 2342 (1992)

  9. In vitro activity of ramoplanin against vancomycin-resistant gram-positive organisms: L.A. Collins, et al.; Antimicrob. Agents Chemother. 37, 1364 (1993)

  10. A new structure for the substrate-binding antibiotic ramoplanin: M.C. Lo, et al.; JACS 123, 8640 (2001)

  11. Ramoplanin. A 16686, A 16686A, MDL 62198:Adis Comments; Drugs R.D. 3, 271 (2002) (Review)

  12. Ramoplanin inhibits bacterial transglycosylases by binding as a dimer to lipid II: Y. Hu, et al.; JACS 125, 8736 (2003)

  13. Chemistry and biology of ramoplanin: a lipoglycodepsipeptide with potent antibiotic activity: S. Walker, et al.; Chem. Rev. 105, 449 (2005) (Review)

  14. Ramoplanin: a lipoglycodepsipeptide antibiotic: D.K. Farver, et al.; Ann. Pharmacother. 39, 863 (2005) (Review)

  15. Lipid II as a target for antibiotics: E. Breukink & B. de Kruijff; Nat. Rev. Drug Discov. 5, 321 (2006) (Review) 

  16. The mechanism of action of ramoplanin and enduracidin: X. Fang, et al.; Mol. Biosyst. 2, 69 (2006)

  17. Cyclic lipodepsipeptides: a new class of antibacterial agents in the battle against resistant bacteria: N. Bionda, et al.; Future Med. Chem. 5, 1311 (2013) (Review)

  18. Identification of a two-component regulatory system involved in antimicrobial peptide resistance in Streptococcus pneumoniae: A.M. Diagne, et al. PLoS Pathog. 18, e1010458 (2022)

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