M-4365 G2
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| Category | Antibiotics |
| Catalog number | BBF-03635 |
| CAS | |
| Molecular Weight | 565.74 |
| Molecular Formula | C31H51NO8 |
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Description
It is produced by the strain of Micromonospora capillate MCRL 0940. M-4365 G2 is mainly resistant to Gram-positive bacteria and mycoplasma, and cross-resistance with other macrolide antibiotics.
Specification
| Synonyms | SCHEMBL192993 |
| IUPAC Name | 2-[(11Z,13Z)-6-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-5,9,13,15-tetramethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde |
| Canonical SMILES | CCC1C(C=C(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC2C(C(CC(O2)C)N(C)C)O)CC=O)C)C)C |
| InChI | InChI=1S/C31H51NO8/c1-9-27-20(4)14-18(2)10-11-25(34)19(3)15-23(12-13-33)30(22(6)26(35)17-28(36)39-27)40-31-29(37)24(32(7)8)16-21(5)38-31/h10-11,13-14,19-24,26-27,29-31,35,37H,9,12,15-17H2,1-8H3/b11-10-,18-14- |
| InChI Key | OBUIQEYZGMZXPJ-RBBIFSNSSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycoplasma |
| Melting Point | 106-110°C |
Reference Reading
1. Hybrid biosynthesis of derivatives of protylonolide and M-4365 by macrolide-producing microorganisms
N Sadakane, Y Tanaka, S Omura J Antibiot (Tokyo). 1982 Jun;35(6):680-7. doi: 10.7164/antibiotics.35.680.
Biotransformation of a macrolide antibiotic and a related compound was studied using various macrolide-producing microorganisms grown in the presence of cerulenin, an inhibitor of de novo synthesis of the aglycone moiety. Protylonolide (1) was transformed into 5-O-(4'-O-propionylmycarosyl)protylonolide (2) by a leucomycin-producing strain, Streptoverticillium kitasatoensis KA-429. M-4365 G2 (3) was bioconverted into M-4365 G3 (4), 9-dihydro M-4365 G3 (5), 3-O-acetyl M-4365 G3 (6) and 3-O-acetyl-9-dihydro M-4365 G3 (7) by a spiramycin-producing strain, Streptomyces ambofaciens KA-1028. Forosaminylated derivatives of M-4365 G2 were not obtained using this microorganism. M-4365 G2 was converted into 3-O-acetyl M-4365 G2 (8) by Stv. kitasatoensis strain KA-429 and a carbomycin-producing strain, S. thermotolerans KA-442. These results suggest that the substrate specificity of mycaminose- and forosamine-binding enzymes is high in Stv. kitasatoensis and S. ambofaciens, respectively, while that of the 3-hydroxyl acylating enzyme and mycarose-binding enzyme is low in these microorganisms. The bioconversion products showed lower antibacterial and antimycoplasmal activities than those of M-4365 G2.
2. Macrolide antibiotics M-4365 produced by Micromonospora. IV. Antimycoplasmal activity of antibiotic M-4365 G2 (de-epoxy rosamicin)
T Onta, I Maezawa, A Kinumaki, S Ohshima, T Yamaguchi J Antibiot (Tokyo). 1981 Jun;34(6):719-26. doi: 10.7164/antibiotics.34.719.
In vitro activities of M-4365 G2, a new basic 16-membered macrolide antibiotic, against a total 19 strains including human, bovine, porcine, rodent, avian and saprophytic mycoplasmas were compared with those of three other macrolide antibiotics, josamycin, erythromycin and tylosin. M-4365 G2 exhibited stronger activities than the other macrolide antibiotics against 11 strains of mycoplasma tested. Especially, its higher activities against M. pneumoniae Mac and FU, U. urealyticum T-960, M. mycoides PG-1 and M. gallisepticum Kp-13, PG-31 and 9-49A were to be noticed (final minimum inhibitory concentrations: 0.0001 approximately 0.049 microgram/ml). Higher antimycoplasmal activity of M-4365 G2 than that of tylosin was also proved in experimental treatment of chickens intranasally inoculated with M. gallisepticum Kp-13 by feeding a diet containing the drug. M. gallisepticum Kp-13 was not isolated from the infected chickens fed a diet containing 0.0063% or more of M-4365 G2.
3. Macrolide antibiotics M-4365 produced by Micromonospora. II. Chemical structures
A Kinumaki, K I Harada, T Suzuki, M Suzuki, T Okuda J Antibiot (Tokyo). 1977 Jun;30(6):450-4. doi: 10.7164/antibiotics.30.450.
By physiochemical analyses and chemical procedures, the structures of a series of basic 16-membered macrolide antibiotics, M-4365, A1, A2, A3, G1, G2 and G3 were elucidated, and it was found that M-4365 A1, G1 and G2 were novel, while M-4365 A2, A3 and G3 were identical with rosamicin, juvenimicins A4 and B1, respectively.
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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 ╳
