Mycoplanecin A
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| Category | Antibiotics |
| Catalog number | BBF-01972 |
| CAS | 72993-51-2 |
| Molecular Weight | 1183.52 |
| Molecular Formula | C61H102N10O13 |
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Description
Mycoplanecin A is a cyclic peptide antibiotic produced by Actinoplanes aivajinensis subsp. mycoplanecinus. It has strong anti-mycobacterial, luteus, and Hypococcus activity. It also has moderate anti-Xanthomonas oryzae activity. It also has antibacterial effect on some strains of Actinomycetes.
Specification
| IUPAC Name | 4-ethyl-N-methyl-1-[3-methyl-2-[methyl(2-oxobutanoyl)amino]butanoyl]-N-[4,11,19,26-tetramethyl-6-(3-methylbutyl)-15,25-bis(2-methylpropyl)-2,5,8,14,17,21,24,27-octaoxo-3-propan-2-yl-20-oxa-1,4,7,13,16,23,26-heptazatricyclo[26.3.0.09,13]hentriacontan-18-yl]pyrrolidine-2-carboxamide |
| Canonical SMILES | CCC1CC(N(C1)C(=O)C(C(C)C)N(C)C(=O)C(=O)CC)C(=O)N(C)C2C(OC(=O)CNC(=O)C(N(C(=O)C3CCCN3C(=O)C(N(C(=O)C(NC(=O)C4CC(CN4C(=O)C(NC2=O)CC(C)C)C)CCC(C)C)C)C(C)C)C)CC(C)C)C |
| InChI | InChI=1S/C61H102N10O13/c1-19-40-29-46(71(32-40)61(83)50(37(11)12)67(17)59(81)47(72)20-2)58(80)68(18)51-39(14)84-48(73)30-62-52(74)44(27-35(7)8)65(15)57(79)43-22-21-25-69(43)60(82)49(36(9)10)66(16)55(77)41(24-23-33(3)4)63-53(75)45-28-38(13)31-70(45)56(78)42(26-34(5)6)64-54(51)76/h33-46,49-51H,19-32H2,1-18H3,(H,62,74)(H,63,75)(H,64,76) |
| InChI Key | ICFLLAYTOVAMGO-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | mycobacteria |
| Density | 1.2 g/cm3 |
Reference Reading
1. Mycoplanecins, novel antimycobacterial antibiotics from Actinoplanes awajinensis subsp. mycoplanecinus subsp. nov. I. Taxonomy of producing organism and fermentation
A Torikata, R Enokita, T Okazaki, M Nakajima, S Iwado, T Haneishi, M Arai J Antibiot (Tokyo). 1983 Aug;36(8):957-60. doi: 10.7164/antibiotics.36.957.
Strain No. 41042, an actinomycete isolated from a soil sample, was found to produce 5-azacytidine and new antibiotics, mycoplanecins. Yellowish brown to yellowish orange color of colonies on agar media, formation of globose to subglobose sporangia bearing motile spores and presence of meso- and hydroxy-diaminopimelic acid and glycine in the cell wall ascribed this strain to genus Actinoplanes. From its morphological, cultural and physiological characteristics, this strain was determined to be a new subspecies of Actinoplanes awajinensis and designated as A. awajinensis subsp. mycoplanecinus subsp. nov. Production of mycoplanecins was carried out by conventional submerged culture: the highest antibiotic titer obtained was 145 micrograms/ml.
2. Mycoplanecins, novel antimycobacterial antibiotics from Actinoplanes awajinensis subsp. mycoplanecinus subsp. nov. II. Isolation, physico-chemical characterization and biological activities of mycoplanecin A
M Nakajima, A Torikata, Y Ichikawa, T Katayama, A Shiraishi, T Haneishi, M Arai J Antibiot (Tokyo). 1983 Aug;36(8):961-6. doi: 10.7164/antibiotics.36.961.
New antibiotics, mycoplanecins, were found in the culture broth of an actinomycete identified as Actinoplanes awajinensis subsp. mycoplanecinus subsp. nov. Mycoplanecin complex was extracted with organic solvents both from the culture filtrate and mycelium and purified by column chromatography on silica gel and Florisil. Mycoplanecin A, a major component, was separated by high performance liquid chromatography on Prep PAK-500/C18 column. The physico-chemical characterization revealed that mycoplanecin A was a new cyclic peptide antibiotic. Mycoplanecins exhibited strong activities primarily against mycobacteria and related microorganisms.
3. Mycoplanecins, novel antimycobacterial antibiotics from Actinoplanes awajinensis subsp. mycoplanecinus subsp. nov. III. Structural determination of mycoplanecin A
M Nakajima, A Torikata, H Tamaoki, T Haneishi, M Arai, T Kinoshita, H Kuwano J Antibiot (Tokyo). 1983 Aug;36(8):967-75. doi: 10.7164/antibiotics.36.967.
The structure of mycoplanecin A was determined by the analysis of chemical degradation products and by mass and 1H and 13C NMR spectrometries. Mycoplanecin A is a new cyclic peptide antibiotic composed of mol each of alpha-ketobutyric acid, glycine, L-leucine, L-proline, L-2-amino-5-methylhexanoic acid, N-methyl-D-leucine, N-methyl-L-threonine, methyl-L-proline and ethyl-L-proline and two mol of N-methyl-L-valine. Among these components, ethyl-L-proline is reported for the first time as a component of natural products. A newly developed mass analysis has been introduced for the differentiation of alpha-amino acid and its N-methyl derivative.
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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 ╳
