Mupirocin Lithium
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| Category | Antibiotics |
| Catalog number | BBF-04554 |
| CAS | 73346-79-9 |
| Molecular Weight | 506.56 |
| Molecular Formula | C26H43LiO9 |
| Purity | ≥95.0% |
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Description
It is a major component of the pseudomonic acid, an antibiotic complex produced by Pseudomonas fluorescens NCIB 10586. It is a carboxylic acid bacteriostatic/bactericidal antibiotic.
Specification
| Related CAS | 12650-69-0 (free acid) |
| Synonyms | L-talo-Non-2-enonic acid, 5,9-anhydro-2,3,4,8-tetradeoxy-8-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]oxiranyl]methyl]-3-methyl-, 8-carboxyoctyl ester, lithium salt, (2E)-; L-talo-Non-2-enonic acid, 5,9-anhydro-2,3,4,8-tetradeoxy-8-[[3-(2-hydroxy-1-methylpropyl)oxiranyl]methyl]-3-methyl-, 8-carboxyoctyl ester, monolithium salt, [2E,8[2S,3S(1S,2S)]]-; Lithium mupirocin; Lithium pseudomonate; Li-MUP |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | lithium;9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]oxynonanoate |
| Canonical SMILES | [Li+].CC(C1C(O1)CC2COC(C(C2O)O)CC(=CC(=O)OCCCCCCCCC(=O)[O-])C)C(C)O |
| InChI | InChI=1S/C26H44O9.Li/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27;/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29);/q;+1/p-1/b16-13+;/t17-,18-,19-,20-,21-,24+,25-,26-;/m0./s1 |
| InChI Key | XFIKMPRBSORKQP-JATHGWPISA-M |
| Source | Pseudomonas Fluorescens |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Bacteria |
| Melting Point | 167-171°C |
| Solubility | Slightly soluble in DMSO, Methanol (Sonicated) |
Reference Reading
1. Evaluation of selective media for bifidobacteria in poultry and rabbit caecal samples
V Rada, K Sirotek, J Petr Zentralbl Veterinarmed B . 1999 Aug;46(6):369-73. doi: 10.1046/j.1439-0450.1999.00241.x.
Five media were evaluated to determine their selectivity for Bifidobacterium sp. in hen and rabbit caecal samples. The colonies arising on the plates inoculated with the caecal samples were Gram stained and screened for the presence of fructose-6-phosphate phosphoketolase activity. Rogosa agar modified by the addition of cysteine-hydrochloride (0.05% w/v), Beeren's agar (with 5 ml/l of propionic acid as a selective agent), BS 2 agar (containing per one litre sodium propionate 15 g, lithium chloride 3 g, paromomycin sulphate 50 mg, neomycin sulphate 200 mg), and Wilkins-Chalgren agar (MW) modified by the addition of acetic acid (1 ml/l) and mupirocin (100 mg/l) were selective for Bifidobacterium sp. from rabbit caecal samples. In contrast, only MW medium was suitable for the isolation and enumeration of bifidobacteria in hen caecal samples. In conclusion, the results suggest that MW agar showed the greatest selectivity. A further advantage of this medium is its case of preparation. Therefore this agar could contribute to the study of the effects of the ingestion both probiotics and prebiotics. Finally, it could be noted that the bifidobacteria selective media should be chosen in respect of the animal species origin of the sample tested.
2. Selective mono-Claisen rearrangement of carbohydrate glycals. A chemical consequence of the vinylogous anomeric effect
D P Curran, Y G Suh Carbohydr Res . 1987 Dec 31;171:161-91. doi: 10.1016/s0008-6215(00)90885-1.
The mono-Claisen rearrangement of carbohydrate glycals is demonstrated to be a synthetically useful and mechanistically significant reaction. Addition of per-O-acetyl glycal-tert-butyldimethylchlorosilane mixture to lithium diisopropylamide generated a bis (or tris)ketenesilylacetal which, upon heating, underwent smooth mono-Claisen rearrangement to provide a C-glycosyl compound after methylation. A second apparently similar Claisen rearrangement required significantly higher temperatures in all cases. Thus, similar hydroxy groups were differentiated without resort to selective protection. A stereoelectronic rationale based on the newly-introduced vinylogous anomeric effect (VAE) is put forth to explain the accelerated Claisen rearrangements of these glycals. Molecular orbital and resonance descriptions of the VAE are included, and the VAE is also used to rationalize ground-state conformational preferences of carbohydrate glycals. The C-glycosyl compounds produced by mono-Claisen rearrangement were suitable for Pd(0)-catalyzed allylic alkylations, providing an unusually facile entry into the pseudomonic acid-ring systems. A nine-step synthesis of a known precursor of pseudomonic acid C is reported.
3. Evaluation of culture media for selective enumeration of bifidobacteria and lactic acid bacteria
Attila Hucker, Judit Süle, Tímea Kõrösi, László Varga Braz J Microbiol . 2014 Oct 9;45(3):1023-30. doi: 10.1590/s1517-83822014000300035.
The purpose of this study was to test the suitability of Transgalactosylated oligosaccharides-mupirocin lithium salt (TOS-MUP) and MRS-clindamycin-ciprofloxacin (MRS-CC) agars, along with several other culture media, for selectively enumerating bifidobacteria and lactic acid bacteria (LAB) species commonly used to make fermented milks. Pure culture suspensions of a total of 13 dairy bacteria strains, belonging to eight species and five genera, were tested for growth capability under various incubation conditions. TOS-MUP agar was successfully used for the selective enumeration of both Bifidobacterium animalis subsp. lactis BB-12 and B. breve M-16 V. MRS-CC agar showed relatively good selectivity for Lactobacillus acidophilus, however, it also promoted the growth of Lb. casei strains. For this reason, MRS-CC agar can only be used as a selective medium for the enumeration of Lb. acidophilus if Lb. casei is not present in a product at levels similar to or exceeding those of Lb. acidophilus. Unlike bifidobacteria and coccus-shaped LAB, all the lactobacilli strains involved in this work were found to grow well in MRS pH 5.4 agar incubated under anaerobiosis at 37 °C for 72 h. Therefore, this method proved to be particularly suitable for the selective enumeration of Lactobacillus spp.
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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 ╳
