Ribostamycin sulfate
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| Category | Antibiotics |
| Catalog number | BBF-03898 |
| CAS | 53797-35-6 |
| Molecular Weight | 552.55 |
| Molecular Formula | C17H36N4O14S |
| Purity | >98% |
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Description
Ribostamycin is an aminoglycoside antibiotic, containing a neutral sugar moiety, and is produced by Streptomyces ribosidificus.
Specification
| Related CAS | 25546-65-0 (free base) |
| Synonyms | Vistamycin Sulfate; Landamycine; Ribomycine |
| Storage | Store at 2-8°C |
| 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;sulfuric acid |
| 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.OS(=O)(=O)O |
| InChI | InChI=1S/C17H34N4O10.H2O4S/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;1-5(2,3)4/h4-17,22-27H,1-3,18-21H2;(H2,1,2,3,4)/t4-,5+,6-,7+,8-,9+,10-,11+,12-,13+,14-,15-,16-,17-;/m0./s1 |
| InChI Key | RTCDDYYZMGGHOE-NMMMDEJWSA-N |
| Source | Streptomyces Ribosidificus |
Properties
| Appearance | White Powder |
| Boiling Point | 907.6°C at 760 mmHg |
| Melting Point | 175-180°C |
| Density | 1.6 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1.Unique O-ribosylation in the biosynthesis of butirosin.
Kudo F1, Fujii T, Kinoshita S, Eguchi T. Bioorg Med Chem. 2007 Jul 1;15(13):4360-8. Epub 2007 Apr 25.
Using a comparative genetics approach, one or more of the BtrA, BtrL, BtrP, and BtrV proteins encoded in the butirosin biosynthetic gene cluster (btr) from Bacillus circulans SANK72073 were identified as being responsible for an O-ribosylation process leading to the formation of ribostamycin, a key intermediate in this, and related antibiotic biosynthetic pathways. Functional analysis of the recombinantly expressed proteins revealed that both BtrL and BtrP were responsible for the ribosylation of neamine, using 5-phosphoribosyl-1-diphosphate (PRPP) as the ribosyl donor. Further detailed analysis indicated that this process occurs via two discrete steps: with BtrL first catalyzing the phosphoribosylaion of neamine to form 5''-phosphoribostamycin, followed by a BtrP-catalyzed dephosphorylation to generate ribostamycin. To the best of our knowledge, this is the first time that the functional characterization of a glycosyltransferase from an aminoglycoside biosynthetic gene cluster has been reported.
2.In vitro activity of amikacin and ten other aminoglycoside antibiotics against gentamicin-resistant bacterial strains.
Reyonolds AV, Hamilton-Miller JM, Brumfitt W. J Infect Dis. 1976 Nov;134 SUPPL:S291-6.
Sixty-nine strains of gentamicin-resistant gram-negative bacilli obtained from different geographical sources were tested for susceptibility to 11 aminoglycoside antibiotics. From the results of determinations of minimal inhibitory concentrations, patterns of resistance were established for 45 strains of Enterobacteriaceae and 24 strains of Pseudomonas aeruginosa. Overall, 81% of the strains were sensitive to amikacin and 33% of the strains were sensitive to butirosin, the next most active compound. Results indicated that 54% of the P. aeruginosa strains were sensitive to amikacin and 33% were sensitive to tobramycin. From resistance patterns, enzymes responsible for inactivation of the antibiotics were deduced. The most common enzyme was aminoglycoside nucleotidyltransferase(2''), either alone or combined with either aminoglycoside phosphotransferase(3')-I or aminoglycoside phosphotransferase(3')-II. Aminoglycoside acetyltransferase(2) was identified exclusively in strains of Providencia stuartii.
3.Biosynthesis of butirosin: transfer and deprotection of the unique amino acid side chain.
Llewellyn NM1, Li Y, Spencer JB. Chem Biol. 2007 Apr;14(4):379-86.
Butirosin, an aminoglycoside antibiotic produced by Bacillus circulans, bears the unique (S)-4-amino-2-hydroxybutyrate (AHBA) side chain, which protects the antibiotic from several common resistance mechanisms. The AHBA side chain is advantageously incorporated into clinically valuable antibiotics such as amikacin and arbekacin by synthetic methods. Therefore, it is of significant interest to explore the biosynthetic origins of this useful moiety. We report here that the AHBA side chain of butirosin is transferred from the acyl carrier protein (ACP) BtrI to the parent aminoglycoside ribostamycin as a gamma-glutamylated dipeptide by the ACP:aminoglycoside acyltransferase BtrH. The protective gamma-glutamyl group is then cleaved by BtrG via an uncommon gamma-glutamyl cyclotransferase mechanism. The application of this pathway to the in vitro enzymatic production of novel AHBA-bearing aminoglycosides is explored with encouraging implications for the preparation of unnatural antibiotics via directed biosynthesis.
4.Ribostamycin production by a mutant of butirosin producing bacteria.
Fujiwara T, Tanimoto T, Matsumoto K, Kondo E. J Antibiot (Tokyo). 1978 Oct;31(10):966-9.
By the use of our improved colony selection technique, xylostasin and ribostamycin producing mutants were isolated from nitrosoguanidine treated Bacillus circulans B15M, a producer of butirosins A and B. Among these structurally related aminoglycosides, ribostamycin is the well-known product of a Steptomyces and has not been isolated as a bacterial metabolite. A selected mutant of strain 306, which produces xylostasin and ribostamycin, was futher mutagenized in expectation of getting an improved strain having the ability to accumulate a large amount of ribostamycin in the culture broth. One mutant, strain 451, derived from strain 306, produced ribostamycin free of xylostasin.
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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 ╳
