Lividomycin A
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| Category | Antibiotics |
| Catalog number | BBF-02655 |
| CAS | 36441-41-5 |
| Molecular Weight | 761.77 |
| Molecular Formula | C29H55N5O18 |
| Purity | 95% |
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Description
It is produced by the strain of Str. lividus 2230-N. It's an aminoglycoside antibiotic. It has a broad-spectrum effect against bacteria and mycobacterium, and has no cross-resistance with Streptomyces and penicillium, and has protective effect on mice infected with S. aureus and Pseudomonas aeruginosa.
Specification
| Synonyms | Antibiotic 2230-B; Antibiotic SF-767A; Antibiotic 503-2; D-Streptamine, O-2-Amino-2,3-Dideoxy-A-D-Ribo-Hexopyranosyl-14-O-[O-A-D-Mannopyranosyl-14-O-2,6-Diamino-2,6-Dideoxy-B-L-Idopyranosyl-13-B-D-Ribofuranosyl-15]-2-Deoxy-; Quintomycin B |
| Storage | Store at 2-8°C |
| IUPAC Name | (2R,3S,4S,5S,6R)-2-[(2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R,5S)-5-[(1R,2R,3S,5R,6S)-3,5-diamino-2-[(2S,3R,5S,6R)-3-amino-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy-4-hydroxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol |
| Canonical SMILES | C1C(C(C(C(C1N)OC2C(CC(C(O2)CO)O)N)OC3C(C(C(O3)CO)OC4C(C(C(C(O4)CN)OC5C(C(C(C(O5)CO)O)O)O)O)N)O)O)N |
| InChI | InChI=1S/C29H55N5O18/c30-3-11-23(51-28-20(43)19(42)17(40)13(5-36)47-28)18(41)15(34)27(45-11)50-24-14(6-37)48-29(21(24)44)52-25-16(39)7(31)1-8(32)22(25)49-26-9(33)2-10(38)12(4-35)46-26/h7-29,35-44H,1-6,30-34H2/t7-,8+,9-,10+,11+,12-,13-,14-,15-,16+,17-,18-,19+,20+,21-,22-,23-,24-,25-,26-,27-,28-,29+/m1/s1 |
| InChI Key | DBLVDAUGBTYDFR-SWMBIRFSSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Mycobacteria |
| Boiling Point | 1068.2°C at 760 mmHg |
| Melting Point | 197-203°C (dec.) |
| Density | 1.65 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1.Aminoglycoside 3'-phosphotransferase III, a new phosphotransferase. Resistance mechanism.
Umezawa Y, Yagisawa M, Sawa T, Takeuchi T, Umezawa H. J Antibiot (Tokyo). 1975 Nov;28(11):845-53.
The aminoglycoside phosphotransferase of Pseudomonas aeruginosa 21-75 was purified by affinity chromatography using dibekacin-Sephadex 4B or lividomycin A-Sepharose 4B followed by DEAE Sephadex A-50 chromatography. It had activities of both the known aminoglycoside 3'-phosphotransferases I and II, and transferred phosphate from ATP to the 3'-hydroxyl group of kanamycin A, ribostamycin and butirosin A and 5-hydroxyl group of lividomycin A. This enzyme was designated aminoglycoside 3'-phosphotransferase III. It showed strong substrate inhibition by kanamycin A and ribostamycin when their concentration exceeded 6 muM. Purification and characterization of this enzyme are reported.
2.Lividomycin resistance in staphylococci by enzymatic phosphorylation.
Kobayashi F, Koshi T, Eda J, Yoshimura Y, Mitsuhashi S. Antimicrob Agents Chemother. 1973 Jul;4(1):1-5.
Enzymatic inactivation of lividomycin (LV) was attempted with nine clinical isolates of staphylococci including LV-susceptible and -resistant strains. LV inactivation and the incorporation into LV of (32)P from gamma-(32)P-adenosine triphosphate were demonstrated in the presence of cell-free extracts from LV-resistant strains but not from LV-susceptible ones. The enzyme was purified approximately 82-fold from a resistant Staphylococcus aureus strain by means of ammonium sulfate fractionation and column chromatography. Some properties of the partially purified LV-phosphorylating enzyme were quite similar to those of an enzyme from Escherichia coli carrying an R factor conferring LV resistance, and the phosphorylated product of the drug was also found to be identical with that produced by E. coli carrying an R factor, i.e., 5''-phosphoryl-LV.
3.Diffusion of aminoglycoside antibiotics across the outer membrane of Escherichia coli.
Nakae R, Nakae T. Antimicrob Agents Chemother. 1982 Oct;22(4):554-9.
The diffusion of aminoglycoside antibiotics (gentamicin, kanamycin, streptomycin, fradiomycin, lividomycin, and mannosylparomomycin) through porin pores was examined in vitro by the liposome swelling technique, using vesicle membranes reconstituted from phospholipids and purified porin trimers. Results showed that aminoglycoside antibiotics diffuse through porin-pores very efficiently, as rapidly as hexoses and disaccharides, despite the fact that the molecular weights of the aminoglycosides used were higher than or close to the exclusion limit of porin pores. The susceptibility to aminoglycoside antibiotics of mutant strains producing 3 to 4% of porin was not significantly different from that of a strain producing a wild-type quantity of porin. These results were interpreted to mean that aminoglycoside antibiotics diffuse through porin-pores very efficiently. Therefore, the diffusion of these drugs through the mutant outer membranes producing 3 to 4% of porin is not a rate-limiting step for aminoglycoside diffusion and its action.
4.Coupling of drug protonation to the specific binding of aminoglycosides to the A site of 16 S rRNA: elucidation of the number of drug amino groups involved and their identities.
Kaul M1, Barbieri CM, Kerrigan JE, Pilch DS. J Mol Biol. 2003 Mar 7;326(5):1373-87.
2-Deoxystreptamine (2-DOS) aminoglycoside antibiotics bind specifically to the central region of the 16S rRNA A site and interfere with protein synthesis. Recently, we have shown that the binding of 2-DOS aminoglycosides to an A site model RNA oligonucleotide is linked to the protonation of drug amino groups. Here, we extend these studies to define the number of amino groups involved as well as their identities. Specifically, we use pH-dependent 15N NMR spectroscopy to determine the pK(a) values of the amino groups in neomycin B, paromomycin I, and lividomycin A sulfate, with the resulting pK(a) values ranging from 6.92 to 9.51. For each drug, the 3-amino group was associated with the lowest pK(a), with this value being 6.92 in neomycin B, 7.07 in paromomycin I, and 7.24 in lividomycin A. In addition, we use buffer-dependent isothermal titration calorimetry (ITC) to determine the number of protons linked to the complexation of the three drugs with the A site model RNA oligomer at pH 5.
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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 ╳
