Maridomycin III
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| Category | Antibiotics |
| Catalog number | BBF-02302 |
| CAS | 35775-82-7 |
| Molecular Weight | 829.97 |
| Molecular Formula | C41H67NO16 |
| Purity | ≥95% |
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Description
It is produced by the strain of Str. hygroscopicus B-5050. It's a macrolide antibiotic. It has the activity against gram-positive bacteria and mycoplasma. Serum dose not affect its antibacterial activity. It has the effect of protecting gram-positive bacterial infection mice, and the therapeutic dose is similar to styloleomycin.
Specification
| Synonyms | Platenomycin C1; Leucomycin V, 12,13-epoxy-12,13-dihydro-, 3,4B-dipropanoate, (12S,13S)-; Antibiotic B 5050C; Antibiotic YL 704C1; Turimycin EP3; Maridomycine; Maridomycinum |
| IUPAC Name | [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-4-(dimethylamino)-5-hydroxy-6-[[(1S,3R,7R,8S,9S,10R,12R,13R,14E,16S)-13-hydroxy-8-methoxy-3,12-dimethyl-5-oxo-10-(2-oxoethyl)-7-propanoyl-4,17-dioxabicyclo[14.1.0]heptadec-14-en-9-yl]oxy]-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] propanoate |
| Canonical SMILES | CCC(=O)C1CC(=O)OC(CC2C(O2)C=CC(C(CC(C(C1OC)OC3C(C(C(C(O3)C)OC4CC(C(C(O4)C)OC(=O)CC)(C)O)N(C)C)O)CC=O)C)O)C |
| InChI | InChI=1S/C41H67NO15/c1-11-27(44)26-19-32(47)51-22(4)18-30-29(54-30)14-13-28(45)21(3)17-25(15-16-43)37(38(26)50-10)57-40-35(48)34(42(8)9)36(23(5)53-40)56-33-20-41(7,49)39(24(6)52-33)55-31(46)12-2/h13-14,16,21-26,28-30,33-40,45,48-49H,11-12,15,17-20H2,1-10H3/b14-13+/t21-,22-,23-,24+,25+,26+,28+,29+,30+,33+,34-,35-,36-,37+,38+,39+,40+,41-/m1/s1 |
| InChI Key | OFBDKNBXULFDFN-FSNMLSSTSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Mycoplasma |
| Boiling Point | 886.7°C at 760 mmHg |
| Melting Point | 135-138°C (dec.) |
| Density | 1.25 g/cm3 |
| Solubility | Soluble in Chloroform, Ethanol |
Reference Reading
1. Microbial transformation of maridomycin III by Serratia marcescens
M Uyeda, K Kubota, S Miyamura, M Shibata J Antibiot (Tokyo). 1983 Dec;36(12):1722-8. doi: 10.7164/antibiotics.36.1722.
Two transformation products of maridomycin (MDM) III, MDM-S1 and MDM-S2 named after Serratia marcescens, were isolated by silica gel chromatography. NMR and IR analysis revealed that MDM-S1 and -S2 had no aldehyde group at C-18 on the macrolactone ring, and that the hydroxyl group at C-9 seemed to disappear. Although MDM-S1 and -S2 are less active against Gram-positive bacteria than starting MDM III they are interesting materials in view of the introduction of nitrogen into each molecule, and that the transformation products are produced by Gram-negative bacteria which are thought to be insensitive to macrolide antibiotics.
2. Microbial transformation of antibiotics II. Additional transformation products of maridomycin III
M Shibata, M Uyeda, S Mori J Antibiot (Tokyo). 1976 Aug;29(8):824-8. doi: 10.7164/antibiotics.29.824.
Streptomyces sp. strain No. K-245 was found to transform maridomycin III into four derivatives (A1, A2, A3 and A4) in addition to the transformation products reported previously. Isolation of the main product A1 was carried out by column chromatography on silica gel developed with CHCl3-MeOH (19:1). From the partial investigation of the structure of A1, it proved to have a C-18-aldehyde group and C 4''-propionyl group but no antimicrobial activity. The relationships between A group's derivatives and known derivatives of maridomycin III are also discussed.
3. I. Isolation and characterization of the transformation products of maridomycin III
M Shibata, M Uyeda, S Mori J Antibiot (Tokyo). 1975 Jun;28(6):434-41. doi: 10.7164/antibiotics.28.434.
Three transformation products of maridomycin (MDM) III, a macrolide antibiotic, by Streptomyces lavendulae were isolated by silica gel and alumina chromatography, and designated as spots 1 (starting MDM III), 2, 3 and 4, in the order of their decreasing Rf values on thin-layer chromatogram. By mass- and NMR-spectrometry and thin-layer chromatography, spot 2 was identified as 18-dihydro-MDM III, spot 3 as 4''-depropionyl-MDM III, and spot 4 as 18-dihydro-4''-depropionyl-MDM III. The relationship between starting MDM III and these transformation products were also discussed.
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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 ╳
