6''-O-Carbamoyltobramycin
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| Category | Antibiotics |
| Catalog number | BBF-02106 |
| CAS | 51736-77-7 |
| Molecular Weight | 510.54 |
| Molecular Formula | C19H38N6O10 |
| Purity | >96% |
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Description
6''-O-Carbamoyltobramycin is an aminoglycoside antibiotic produced by Streptomyces tenebrarius. 6''-O-Carbamoyltobramycin has a broad antibacterial spectrum and has a strong effect on Gram-positive and negative bacteria and mycobacteria.
Specification
| Synonyms | Nebramycin V'; Nebramycin factor 5'; Nebramycin-5'; 6-O-Carbamoyltob; (1S,2S,3R,4S,6R)-4,6-diamino-3-[(2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl)oxy]-2-hydroxycyclohexyl 3-amino-6-O-carbamoyl-3-deoxy-alpha-D-glucopyranoside |
| IUPAC Name | [(2R,3S,4S,5R,6S)-4-amino-6-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-3,5-dihydroxyoxan-2-yl]methyl carbamate |
| Canonical SMILES | C1C(C(C(C(C1N)OC2C(C(C(C(O2)COC(=O)N)O)N)O)O)OC3C(CC(C(O3)CN)O)N)N |
| InChI | InChI=1S/C19H38N6O10/c20-3-9-8(26)2-7(23)17(32-9)34-15-5(21)1-6(22)16(14(15)29)35-18-13(28)11(24)12(27)10(33-18)4-31-19(25)30/h5-18,26-29H,1-4,20-24H2,(H2,25,30)/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+/m0/s1 |
| InChI Key | YPPFEJHOHNPKLT-PBSUHMDJSA-N |
Properties
| Appearance | White Amorphous Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; mycobacteria |
| Boiling Point | 840.8°C at 760 mmHg |
| Density | 1.54 g/cm3 |
Reference Reading
1. The nebramycin aminoglycoside profiles of Streptomyces tenebrarius and their characterization using an integrated liquid chromatography-electrospray ionization-tandem mass spectrometric analysis
Je Won Park, Sung Ryeol Park, Ah Reum Han, Yeon Hee Ban, Young Ji Yoo, Eun Ji Kim, Yeo Joon Yoon Anal Chim Acta. 2010 Feb 19;661(1):76-84. doi: 10.1016/j.aca.2009.12.014. Epub 2009 Dec 21.
The development of an efficient analytical protocol for the reliable identification of the biosynthetic intermediates found in microbial cultures, which usually produce complex intermediates of the metabolites of interest, is both challenging and essential for further studies into gene-to-metabolite networks. A simple and highly selective method for detecting the biosynthetic intermediates involved in the aminoglycosidic nebramycin pathway of Streptomyces tenebrarius was developed and validated. Cleanup utilizing a solid-phase extraction (OASIS MCX SPE) technique provides a simple and reproducible method for extracting the nebramycin factors from a fermentation broth. The separation of each factor through a reversed-phase C(18) column using an ion-pairing reagent allowed the simultaneous profiling of the aminoglycosides. By employing the authentic tobramycin spiked into a blank fermentation medium, the combined use of acid extraction, OASIS MCX SPE cleanup, and HFBA (heptafluorobutyric acid)-mediated chromatographic separation coupled with electrospray ionization-tandem mass spectrometry (ESI-MS/MS) detection was proven to be sufficiently accurate and reliable to analyze the nebramycin factors produced in a culture broth. The detection limit of tobramycin spiked in the culture broth was approximately 1.8 ng mL(-1). The mean recovery ranged from 89 to 92%, the intra- and inter-day precision (RSD) was <6% and their accuracy ranged from 88 to 93%. A total of nine nebramycin factors including apramycin, 6''-O-carbamoylkanamycin B, 6''-O-carbamoyltobramycin, 3'-hydoxyapramycin, tobramycin, kanamycin B, NK-1012-1, nebramine, and neamine were identified. This is the first report on the integrated LC-ESI-MS/MS characterization of a wide range of nebramycin factors from a bacterial fermentation broth.
2. Selective quantitative determination of tobramycin from fermentation broth
G B Kiss, V Széll, G Ambrus, I Ott Acta Microbiol Hung. 1988;35(2):89-92.
A derivative of Rhizobium meliloti 41 was constructed (strain GY654) which was resistant to apramycin and kanamycin but remained sensitive to tobramycin. Strain GY654 selectively measures tobramycin and 6"-O-carbamoyltobramycin in the presence of apramycin, kanamycin and 6"-O-carbamoylkanamycin B, therefore it is suitable for the rapid quantitation of 6"-O-carbamoyltobramycin and tobramycin in fermentation broths of Streptomyces tenebrarius and solvents containing antibiotic mixtures.
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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 ╳
