Leucomycin A5
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| Category | Antibiotics |
| Catalog number | BBF-02649 |
| CAS | 18361-45-0 |
| Molecular Weight | 771.94 |
| Molecular Formula | C39H65NO14 |
| Purity | >98% by HPLC |
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Description
It is produced by the strain of Str. kitasatoensis. It's a macrolide antibiotic. It has strong anti-gram-positive bacterial effect, and also has an effect on spirochetes, rickettsium and Chlamydia. After the C3 position on the lactone ring in the structure is acetylated, the activity in vitro is reduced, but the activity in vivo is enhanced, and the toxicity is also reduced. The antibacterial activity of Leucomycin group A is stronger than group B. It has been used in clinical and the indications are the same as erythromycin.
Specification
| Synonyms | Kitasamycin A5; Turimycin H4; Leukomycin A5; Leucomycin V 4''-butanoate |
| Storage | Store at -20°C |
| IUPAC Name | [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] butanoate |
| Canonical SMILES | CCCC(=O)OC1C(OC(CC1(C)O)OC2C(OC(C(C2N(C)C)O)OC3C(CC(C(C=CC=CCC(OC(=O)CC(C3OC)O)C)O)C)CC=O)C)C |
| InChI | InChI=1S/C39H65NO14/c1-10-14-29(44)52-37-25(5)50-31(21-39(37,6)47)53-34-24(4)51-38(33(46)32(34)40(7)8)54-35-26(17-18-41)19-22(2)27(42)16-13-11-12-15-23(3)49-30(45)20-28(43)36(35)48-9/h11-13,16,18,22-28,31-38,42-43,46-47H,10,14-15,17,19-21H2,1-9H3/b12-11+,16-13+/t22-,23-,24-,25+,26+,27+,28-,31+,32-,33-,34-,35+,36+,37+,38+,39-/m1/s1 |
| InChI Key | JZVYPSLDMXOITF-MJRCUCNNSA-N |
| Source | Streptomyces kisatoensis |
Properties
| Appearance | White Columnar Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Mycoplasma |
| Boiling Point | 871.4°C at 760 mmHg |
| Melting Point | 120-123°C |
| Density | 1.22 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform, Ethanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. High-throughput screening for multi-class veterinary drug residues in animal muscle using liquid chromatography/tandem mass spectrometry with on-line solid-phase extraction
Shirley Sau-Ling Lai, Hubert Po-On Tang, Clare Ho Rapid Commun Mass Spectrom . 2006;20(17):2565-72. doi: 10.1002/rcm.2635.
A rapid qualitative method using on-line column-switching liquid chromatography/tandem mass spectrometry (LC/MS/MS) was developed and validated for screening 13 target veterinary drugs: four macrolides - erythromycin A, josamycin (leucomycin A3), kitasamycin (leucomycin A5), and tylosin A; six (fluoro)quinolones - ciprofloxacin, danofloxacin, enrofloxacin, flumequine, oxolinic acid, and sarafloxacin; and lincomycin, virginiamycin M1, and trimethoprim in different animal muscles. Clindamycin, norfloxacin, nalidixic acid, oleandomycin, ormetoprim, and roxithromycin were used as the internal standards. After simple deproteination and analyte extraction of muscle samples using acetonitrile, the supernatant was subjected to on-line cleanup and direct analysis by LC/MS/MS. On-line cleanup with an extraction cartridge packed with hydrophilic-hydrophobic polymer sorbent followed by fast LC using a short C18 column resulted in a total analysis cycle of 6 min for 19 drugs. This screening method considerably reduced the time and the cost for the quantitative and confirmatory analyses. The application of a control point approach was also introduced and explained.
2. [Identification of the components and products of hydrolysis in acetylleucomycin by LC-MS]
Min Hu, Chang-Qin Hu Yao Xue Xue Bao . 2006 May;41(5):476-80.
Aim:To identify the components of acetylleucomycin and its hydrolytic products by LC-MS.Methods:Acetylleucomycin was separated on a Diamonsil C18 column with 0.1 mol x L(-1) ammonium acetate-acetontrile (35 : 65) as mobile phase. The LC-MS was equipped with an electorspray ion source (ESI), which was set at the positive ion mode, and the mass spectra of each component in chromatogram were obtained with difference cone voltage.Results:The components of acetylleucomycin and its hydrolytic products can be separated by HPLC. The components were identified according to the molecular weight and its major mass fragment ions. The major components identified in domastic acetylleucomycin were acetylleucomycin A4, A5; acetylleucomycin A1, A3; acetylleucomycin A6, A7, and acetylleucomycin A13. The hydrolytic products of acetylleucomycin were not kitasamycin, but some non-complete hydrolytic product.Conclusion:The method is rapid, sensitive and specific. It' s suitable to application in the fields of multi-components antibiotics analysis.
3. Adhesive binding of rokitamycin to Staphylococcus aureus ribosomes
Y Nakajima, M Matsuoka, K Endou FEMS Microbiol Lett . 1990 Oct;60(1-2):93-6. doi: 10.1016/0378-1097(90)90351-p.
Rokitamycin (RKM), a 3"-O-propionyl derivative of leucomycin A5, is bactericidal against staphylococci near the minimum inhibitory concentrations. RKM bound to ribosomes before-hand is only slightly displaced by erythromycin or josamycin, or even by RKM itself. The adhesive binding of the RKM-ribosome complex might prove to be the lethal event for susceptible staphylococci.
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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 ╳
