CAS 76168-82-6|ramoplanin A2
| Common Name | ramoplanin A2 | ||
|---|---|---|---|
| CAS Number | 76168-82-6 | Molecular Weight | 2554.066 |
| Density | 1.5±0.1 g/cm3 | Boiling Point | / |
| Molecular Formula | C106H170ClN21O30 | Melting Point | >218 °C(dec.) |
| MSDS | ChineseUSA | Flash Point | / |
| Symbol | GHS05 | Signal Word | Danger |
Names
| Name | Ramoplanin |
|---|---|
| Synonym | More Synonyms |
ramoplanin A2 BiologicalActivity
| Description | Ramoplanin is a broad-spectrum lipoglycodepsipeptide antibiotic derived from the Actinoplanes spp with with activity against gram-positive bacteria[1][2]. |
|---|---|
| Related Catalog | Research Areas >>InfectionSignaling Pathways >>Anti-infection >>Bacterial |
| Target | Bacteria[1] |
| In Vitro | Ramoplanin exerts its bactericidal activity against gram-positive aerobic and anaerobic bacteria by blocking peptidoglycan synthesis via lipid II[1]. |
| In Vivo | Ramoplanin (100, 500 μg/ml; p.o.; for 8 days) suppresses vancomycin-resistant Enterococcus (VRE) to undetectable level during treatment[1]. Animal Model: Female CF1 mice (25-30 g)[1] Dosage: 100 μg/ml, 500 μg/ml Administration: Oral administration; for 8 days Result: Developed undetectable levels of VRE in stool during treatment. |
| References | [1]. Stiefel U, et al. Efficacy of oral ramoplanin for inhibition of intestinal colonization by vancomycin-resistant enterococci in mice. Antimicrob Agents Chemother. 2004 Jun;48(6):2144-8. [2]. Cheng M, et al. Ramoplanin at bactericidal concentrations induces bacterial membrane depolarization in Staphylococcus aureus. Antimicrob Agents Chemother. 2014 Nov;58(11):6819-27. |
Chemical & Physical Properties
| Density | 1.5±0.1 g/cm3 |
|---|---|
| Melting Point | >218 °C(dec.) |
| Molecular Formula | C106H170ClN21O30 |
| Molecular Weight | 2554.066 |
| Exact Mass | 2552.035156 |
| LogP | -6.39 |
| Index of Refraction | 1.689 |
| Storage condition | -20°C |
Safety Information
| Symbol | GHS05 |
|---|---|
| Signal Word | Danger |
| Hazard Statements | H318 |
| Precautionary Statements | P280-P305 + P351 + P338 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | C |
| RIDADR | NONH for all modes of transport |
| RTECS | VE5050000 |
Articles31
More Articles| Functional identification of the gene encoding the enzyme involved in mannosylation in ramoplanin biosynthesis in Actinoplanes sp. Biotechnol. Lett. 35(9) , 1501-8, (2013) Ramoplanin is a lipopeptide antibiotic active against multi-drug-resistant, Gram-positive pathogens. Structurally, it contains a di-mannose moiety attached to the peptide core at Hpg(11). The biosynth... | |
| Dissecting ramoplanin: mechanistic analysis of synthetic ramoplanin analogues as a guide to the design of improved antibiotics. J. Am. Chem. Soc. 126(24) , 7462-3, (2004) Ramoplanin is a potent cyclic lipoglycodepsipeptide antibiotic that disrupts bacterial cell wall synthesis by binding to the peptidoglycan intermediate Lipid II and blocking its polymerization to form... | |
| Total synthesis and examination of three key analogues of ramoplanin: a lipoglycodepsipeptide with potent antibiotic activity. J. Am. Chem. Soc. 126(4) , 1041-3, (2004) The total synthesis and evaluation of three key ramoplanin aglycon analogues are detailed. The first (5a) represents replacement of the labile depsipeptide ester with a stable amide (HAsn2 --> Dap2) w... |
Synonyms
| A 16686A |
| N-[(3S,6R,9S,15S,18R,21S,24R,27S,30S,33R,36S,39R,42R,45R,48S,49S)-24,42-Bis(3-aminopropyl)-27-benzyl-49-carbamoyl-3-(3-chloro-4-hydroxyphenyl)-18,39-bis[(1R)-1-hydroxyethyl]-30-[(1S)-1-hydroxyethyl ]-15,33,36,45-tetrakis(4-hydroxyphenyl)-9-isobutyl-21-(4-{[2-O-(α-D-mannopyranosyl)-α-D-mannopyranosyl]oxy}phenyl)-6-methyl-2,5,8,11,14,17,20,23,26,29,32,35,38,41,44,47-hexadecaoxo-1-oxa-4,7,1
 0,13,16,19,22,25,28,31,34,37,40,43,46-pentad |
| L-Aspartamide, N-[(3S,6R,9S,15S,18R,21S,24R,27S,30S,33R,36S,39R,42R,45R,48S,49S)-49-(aminocarbonyl)-24,42-bis(3-aminopropyl)-3-(3-chloro-4-hydroxyphenyl)-18,39-bis[(1R)-1-hydroxyethyl]-30-[(1S)-1-h ;ydroxyethyl]-15,33,36,45-tetrakis(4-hydroxyphenyl)-21-[4-[(2-O-α-D-mannopyranosyl-α-D-mannopyranosyl)oxy]phenyl]-6-methyl-9-(2-methylpropyl)-2,5,8,11,14,17,20,23,26,29,32,35,38,41,44,47-hexade caoxo-27-(phenylmethyl)-1-oxa-4,7,10,13,16,1 |
| ramoplanin A2 |
| A 16686 |
| Antibiotic A 16686 |
