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Ramoplanin Complex

(Synonyms: 雷莫拉宁) 目录号 : GC48025

An antibiotic complex

Ramoplanin Complex Chemical Structure

Cas No.:76168-82-6

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10 mg
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50 mg
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100 mg
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250 mg
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产品描述

Ramoplanin complex is a mixture of ramoplanin A1, -A2, and -A3 originally isolated from Actinoplanes that has antibacterial activity.1,2,3 Ramoplanin complex is active against clinical isolates of the Gram-positive bacteria S. aureus, S. pyogenes, S. pneumoniae, and S. faecalis (MICs = 0.016-2 &#181g/ml) but not Gram-negative bacteria or C. albicans (MICs = ≥128 &#181g/ml).2 It inhibits cell wall synthesis in B. subtilis when used at a concentration of 0.5 &#181g/ml.1 Ramoplanin complex is effective against systemic S. pyogenes, S. pneumoniae, and S. aureus infections in mice with ED50 values of 0.081, 0.14, and approximately 25 mg/kg per day, respectively.

1.Cavalleri, B., Pagani, H., Volpe, G., et al.A-16686, a new antibiotic from actinoplanes. I. Fermentation, isolation and preliminary physico-chemical characteristicsJ. Antibiot. (Tokyo)37(4)309-317(1984) 2.Pallanza, R., Berti, M., Scotti, R., et al.A-16686, a new antibiotic from actinoplanes. II. Biological propertiesJ. Antibiot. (Tokyo)37(4)318-324(1984) 3.Shin, D., Rew, Y., and Boger, D.L.Total synthesis and structure of the ramoplanin A1 and A3 aglycons: Two minor components of the ramoplanin complexProc. Natl. Acad. Sci. USA101(33)11977-11979(2004)

Chemical Properties

Cas No. 76168-82-6 SDF
别名 雷莫拉宁
Canonical SMILES OC(C=C1)=CC=C1[C@H](C(N[C@H](CCCN)C(N[C@@]([C@H](O)C)([H])C(N[C@@H](C2=CC=C(O)C=C2)C(N[C@H](C3=CC=C(O)C=C3)C(NC([C@H](C)O)C(N[C@@H](CC4=CC=CC=C4)C(N[C@H](CCCN)C(N[C@@H](C5=CC=C(O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]6O[C@]7([H])[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O7)C=C5)C8=O)=O)=O)=O)=O)=O)=O)=O)=O)NC([C@@H](NC([C@@H](NC(/C=C\C=C\CCC)=O)CC(N)=O)=O)[C@@H](C(N)=O)OC([C@]([H])(C9=CC=C(O)C(Cl)=C9)NC([C@@H](C)NC([C@H](CC(C)C)NC(CNC([C@H](C%10=CC=C(O)C=C%10)NC([C@]([C@H](O)C)([H])N8)=O)=O)=O)=O)=O)=O)=O.OC(C=C%11)=CC=C%11[C@H](C(N[C@H](CCCN)C(N[C@@]([C@H](O)C)([H])C(N[C@@H](C%12=CC=C(O)C=C%12)C(N[C@H](C%13=CC=C(O)C=C%13)C(NC([C@H](C)O)C(N[C@@H](CC%14=CC=CC=C%14)C(N[C@H](CCCN)C(N[C@@H](C%15=CC=C(O[C@H]%16O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%16O[C@]%17([H])[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O%17)C=C%15)C%18=O)=O)=O)=O)=O)=O)=O)=O)=O)NC([C@@H](NC([C@@H](NC(/C=C\C=C\CC(C)C)=O)CC(N)=O)=O)[C@@H](C(N)=O)OC([C@]([H])(C%19=CC=C(O)C(Cl)=C%19)NC([C@@H](C)NC([C@H](CC(C)C)NC(CNC([C@H](C%20=CC=C(O)C=C%20)NC([C@]([C@H](O)C)([H])N%18)=O)=O)=O)=O)=O)=O)=O.OC(C=C%21)=CC=C%21[C@H](C(N[C@H](CCCN)C(N[C@@]([C@H](O)C)([H])C(N[C@@H](C%22=CC=C(O)C=C%22)C(N[C@H](C%23=CC=C(O)C=C%23)C(NC([C@H](C)O)C(N[C@@H](CC%24=CC=CC=C%24)C(N[C@H](CCCN)C(N[C@@H](C%25=CC=C(O[C@H]%26O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%26O[C@]%27([H])[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O%27)C=C%25)C%28=O)=O)=O)=O)=O)=O)=O)=O)=O)NC([C@@H](NC([C@@H](NC(/C=C\C=C\CCC(C)C)=O)CC(N)=O)=O)[C@@H](C(N)=O)OC([C@]([H])(C%29=CC=C(O)C(Cl)=C%29)NC([C@@H](C)NC([C@H](CC(C)C)NC(CNC([C@H](C%30=CC=C(O)C=C%30)NC([C@]([C@H](O)C)([H])N%28)=O)=O)=O)=O)=O)=O)=O
分子式 C119H154ClN21O40 (for A2) 分子量 2554.1
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1 mM 0.3915 mL 1.9576 mL 3.9153 mL
5 mM 0.0783 mL 0.3915 mL 0.7831 mL
10 mM 0.0392 mL 0.1958 mL 0.3915 mL
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Research Update

Total synthesis and structure of the ramoplanin A1 and A3 aglycons: two minor components of the Ramoplanin Complex

Proc Natl Acad Sci U S A 2004 Aug 17;101(33):11977-9.PMID:15175429DOI:10.1073/pnas.0401419101.

Ramoplanin is a potent antibiotic, first disclosed in 1984, that acts by inhibiting bacterial cell-wall biosynthesis. The original Ramoplanin Complex was shown to consist of a mixture of three closely related compounds, ramoplanin A1-A3, of which ramoplanin A2 is the most abundant. The structure of ramoplanin A2 was unambiguously established first through a series of extensive spectroscopic studies, allowing complete stereochemical assignments and subsequently providing a minor reassignment of the side-chain double-bond stereochemistry and, most recently, through total synthesis of authentic material. Here we report the total syntheses of the aglycons of the minor components of the Ramoplanin Complex, A1 and A3, which unambiguously establish their structure and provide an expected structural revision for the lipid side-chain double-bond stereochemistry.