Ribostamycin
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| Category | Antibiotics |
| Catalog number | BBF-02683 |
| CAS | 25546-65-0 |
| Molecular Weight | 454.47 |
| Molecular Formula | C17H34N4O10 |
| Purity | 95% |
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Description
Ribostamycin is an antibiotic produced by Streptomyces ribosidifcus. It is active against gram-positive bacteria.
Specification
| Synonyms | Vistamycin; Hetangmycin; Xylostatin; Antibiotic SF 733; SF-733; SF 733 |
| Storage | 2-8ºC |
| IUPAC Name | (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol |
| Canonical SMILES | C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)N)OC3C(C(C(O3)CO)O)O)O)N |
| InChI | InChI=1S/C17H34N4O10/c18-2-6-10(24)12(26)8(21)16(28-6)30-14-5(20)1-4(19)9(23)15(14)31-17-13(27)11(25)7(3-22)29-17/h4-17,22-27H,1-3,18-21H2/t4-,5+,6-,7-,8-,9+,10-,11-,12-,13-,14-,15-,16-,17+/m1/s1 |
| InChI Key | NSKGQURZWSPSBC-VVPCINPTSA-N |
Properties
| Appearance | Needle Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 769.8±60.0°C at 760 mmHg |
| Melting Point | 192-195°C (dec.) |
| Density | 1.6±0.1 g/cm3 |
Reference Reading
1.Aminoglycoside Antibiotics: New Insights into the Biosynthetic Machinery of Old Drugs.
Kudo F1, Eguchi T2. Chem Rec. 2016 Feb;16(1):4-18. doi: 10.1002/tcr.201500210. Epub 2015 Oct 12.
2-Deoxystreptamine (2DOS) is the unique chemically stable aminocyclitol scaffold of clinically important aminoglycoside antibiotics such as neomycin, kanamycin, and gentamicin, which are produced by Actinomycetes. The 2DOS core can be decorated with various deoxyaminosugars to make structurally diverse pseudo-oligosaccharides. After the discovery of biosynthetic gene clusters for 2DOS-containing aminoglycoside antibiotics, the function of each biosynthetic enzyme has been extensively elucidated. The common biosynthetic intermediates 2DOS, paromamine and ribostamycin are constructed by conserved enzymes encoded in the gene clusters. The biosynthetic intermediates are then converted to characteristic architectures by unique enzymes encoded in each biosynthetic gene cluster. In this Personal Account, we summarize both common biosynthetic pathways and the pathways used for structural diversification.
2.Chemically related 4,5-linked aminoglycoside antibiotics drive subunit rotation in opposite directions.
Wasserman MR1, Pulk A2, Zhou Z1, Altman RB1, Zinder JC3, Green KD4, Garneau-Tsodikova S4, Doudna Cate JH2, Blanchard SC5. Nat Commun. 2015 Jul 30;6:7896. doi: 10.1038/ncomms8896.
Dynamic remodelling of intersubunit bridge B2, a conserved RNA domain of the bacterial ribosome connecting helices 44 (h44) and 69 (H69) of the small and large subunit, respectively, impacts translation by controlling intersubunit rotation. Here we show that aminoglycosides chemically related to neomycin-paromomycin, ribostamycin and neamine-each bind to sites within h44 and H69 to perturb bridge B2 and affect subunit rotation. Neomycin and paromomycin, which only differ by their ring-I 6'-polar group, drive subunit rotation in opposite directions. This suggests that their distinct actions hinge on the 6'-substituent and the drug's net positive charge. By solving the crystal structure of the paromomycin-ribosome complex, we observe specific contacts between the apical tip of H69 and the 6'-hydroxyl on paromomycin from within the drug's canonical h44-binding site. These results indicate that aminoglycoside actions must be framed in the context of bridge B2 and their regulation of subunit rotation.
3.Potentiation of aminoglycoside activity in Pseudomonas aeruginosa by targeting the AmgRS envelope stress-responsive two-component system.
Poole K1, Gilmour C2, Farha MA3, Mullen E2, Lau CH2, Brown ED3. Antimicrob Agents Chemother. 2016 Mar 28. pii: AAC.03069-15. [Epub ahead of print]
A screen for agents that potentiated the activity of paromomycin (PAR), a 4,5-linked aminoglycoside (AG), against wild typePseudomonas aeruginosaidentified the RNA polymerase inhibitor, rifampicin (RIF). RIF potentiated additional 4,5-linked AGs such as neomycin and ribostamycin but not the clinically-important 4,6-linked AGs amikacin and gentamicin. Potentiation was absent in a mutant lacking the AmgRS envelope stress response two-component system (TCS), which protects the organism from AG-generated membrane-damaging aberrant polypeptides and, thus, promotes AG resistance, an indication that RIF was acting via this TCS in potentiating 4,5-linked AG activity. Potentiation was also absent in a RIF-resistant RNA polymerase mutant, consistent with its potentiation of AG activity being dependent on RNA polymerase perturbation. PAR-inducible expression of the AmgRS-dependent geneshtpXandyccAwas reduced by RIF, suggesting that AG activation of this TCS was compromised by this agent.
4.Defining RNA motif-aminoglycoside interactions via two-dimensional combinatorial screening and structure-activity relationships through sequencing.
Velagapudi SP1, Disney MD. Bioorg Med Chem. 2013 Oct 15;21(20):6132-8. doi: 10.1016/j.bmc.2013.04.072. Epub 2013 May 7.
RNA is an extremely important target for the development of chemical probes of function or small molecule therapeutics. Aminoglycosides are the most well studied class of small molecules to target RNA. However, the RNA motifs outside of the bacterial rRNA A-site that are likely to be bound by these compounds in biological systems is largely unknown. If such information were known, it could allow for aminoglycosides to be exploited to target other RNAs and, in addition, could provide invaluable insights into potential bystander targets of these clinically used drugs. We utilized two-dimensional combinatorial screening (2DCS), a library-versus-library screening approach, to select the motifs displayed in a 3×3 nucleotide internal loop library and in a 6-nucleotide hairpin library that bind with high affinity and selectivity to six aminoglycoside derivatives. The selected RNA motifs were then analyzed using structure-activity relationships through sequencing (StARTS), a statistical approach that defines the privileged RNA motif space that binds a small molecule.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
