Fortimicin B
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| Category | Antibiotics |
| Catalog number | BBF-01435 |
| CAS | 54783-95-8 |
| Molecular Weight | 348.44 |
| Molecular Formula | C15H32N4O5 |
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Description
Produced by the strain of Micromonospora olivoasterospora, it has a weak antibacterial activity.
Specification
| Synonyms | Astromicin B; 4-Amino-1,4-dideoxy-3-O-(2,6-diamino-2,3,4,6,7-pentadeoxy-beta-L-lyxo-heptopyranosyl)-6-O-methyl-1-(methylamino)-L-chiro-inositol |
| IUPAC Name | (1S,2S,3R,4R,5S,6R)-2-amino-3-[(2R,3R,6S)-3-amino-6-[(1S)-1-aminoethyl]oxan-2-yl]oxy-6-methoxy-5-(methylamino)cyclohexane-1,4-diol |
| Canonical SMILES | CC(C1CCC(C(O1)OC2C(C(C(C(C2O)NC)OC)O)N)N)N |
| InChI | InChI=1S/C15H32N4O5/c1-6(16)8-5-4-7(17)15(23-8)24-13-9(18)11(20)14(22-3)10(19-2)12(13)21/h6-15,19-21H,4-5,16-18H2,1-3H3/t6-,7+,8-,9-,10-,11-,12+,13+,14+,15+/m0/s1 |
| InChI Key | WFMQYKIRAVMXSU-LCVFDZPESA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; fungi |
| Boiling Point | 532°C at 760 mmHg |
| Melting Point | 101-103°C |
| Density | 1.26 g/cm3 |
Reference Reading
1. Characterization of fortimicin aminoglycoside profiles produced from Micromonospora olivasterospora DSM 43868 by high-performance liquid chromatography-electrospray ionization-ion trap-mass spectrometry
Nguyen Lan Huong, Nguyen Huu Hoang, Sung-Yong Hong, Jae Kyung Sohng, Yeo Joon Yoon, Je Won Park Anal Bioanal Chem. 2016 Feb;408(6):1667-78. doi: 10.1007/s00216-015-9281-2. Epub 2016 Jan 11.
In this study, an efficient high-performance liquid chromatography (HPLC)-electrospray ionization (ESI)-ion trap-tandem mass spectrometry (MS/MS) was developed for the identification of the biosynthetic congeners involved in the aminocyclitol aminoglycosidic fortimicin pathway from Micromonospora olivasterospora fermentation. The usage of both acid extraction (pH ~2.5) followed by an cationic-exchanging SPE cleanup and pentafluoropropionic acid mediated ion-pairing chromatography with ESI-ion trap-MS/MS detection was determined to be sufficiently practical to profile the fortimicin (FOR) congeners produced in a culture broth. The limit of the quantification for the fortimicin A (FOR-A) standard spiked in the culture broth was ~1.6 ng mL(-1). The average recovery rate was 93.6%, and the intra- and inter-day precisions were <5% with accuracy in the range from 87.1 to 94.2%. Moreover, the epimeric mixtures including FOR-KH, FOR-KR, and FOR-B were separately resolved through a macrocyclic glycopeptide (teicoplanin)-bonded chiral column. As a result, ten natural FOR pseudodisaccharide analogs were identified and semi-quantified in descending order as follows: FOR-A, FOR-B, DCM, FOR-KH plus FOR-KR, FOR-KK1, FOR-AP, FOR-KL1, FOR-AO, and FOR-FU-10. This is the first report on both the simultaneous characterization of diverse structurally closely related FORs derived from bacterial fermentation using HPLC-ESI-ion trap-MS/MS analysis and the chromatographic separation of the three FOR epimers.
2. Comparison of fortimicins with other aminoglycosides and effects on bacterial ribosome and protein synthesis
N Moreau, C Jaxel, F Le Goffic Antimicrob Agents Chemother. 1984 Dec;26(6):857-62. doi: 10.1128/AAC.26.6.857.
Fortimicins are bicyclic aminoglycoside antibiotics that contain a fortamine moiety instead of the deoxystreptamine found in other aminoglysides. Fortimicin A had a bactericidal effect on Escherichia coli and Staphylococcus epidermidis and was found to inhibit protein synthesis in vivo. In vitro, fortimicin A inhibited polyuridylic acid-directed phenylalanine polymerization and induced misreading, as shown by leucine incorporation. In contrast, fortimicin B had no effect on either polymerization or misreading. In assays programmed with natural mRNA, only a weak polymerization inhibition effect was observed with fortimicin A, whereas a strong stimulation was seen in the presence of fortimicin B. Both fortimicins A and B inhibited dissociation of 70S ribosomes into their subunits and neither was able to displace [3H]dihydrostreptomycin, [3H]tobramycin, or [3H]gentamicin from their respective binding sites on the 70S particle.
3. Diastereomeric fortimicin 1,2-epoxides. The preparation of the 1-deamino-2-deoxyfortimicins A and B and the 1,2-di-epi-fortimicins A and B
J R Martin, P Johnson, J Tadanier, M Cirovic, R S Stanaszek J Antibiot (Tokyo). 1982 Jan;35(1):46-57. doi: 10.7164/antibiotics.35.46.
The preparation of 1,2-anhydro-2',6'-di-N-benzyloxycarbonyl-1-deaminofortimicin B-4,5-carbamate (4) and its conversion to the two diastereomeric 2',6'-di-N-benzyloxycarbonyl-1-deamino-2-deoxy-1,2-epoxyfortimicin B-4,5-carbamates 7 and 13 are described. The olefin 4 was used for preparation of 1-deamino-2-deoxyfortimicin A (6d) while the beta-epoxide 13 was used for the preparation of 1,2-di-epi-fortimicin A (17b) and 2-amino-1-deamino-2-deoxy-1-hydroxyfortimicin A (19c). The in vitro antibacterial activities of 6d, 17b and 19c are reported.
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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 ╳
