Monamycin C
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| Category | Antibiotics |
| Catalog number | BBF-01956 |
| CAS | 31764-92-8 |
| Molecular Weight | 691.86 |
| Molecular Formula | C34H57N7O8 |
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Description
Monamycin C is an ester peptide antibiotic produced by Str. jamaicensis A-154. Activity against gram-positive bacteria.
Specification
| Storage | Store at -20°C |
| IUPAC Name | 23-butan-2-yl-6-hydroxy-10,15-dimethyl-11-(2-methylpropyl)-20-propan-2-yl-22-oxa-3,4,10,13,19,25,26-heptazatetracyclo[23.4.0.03,8.013,17]nonacosane-2,9,12,18,21,24-hexone |
| Canonical SMILES | CCC(C)C1C(=O)N2C(CCCN2)C(=O)N3C(CC(CN3)O)C(=O)N(C(C(=O)N4CC(CC4C(=O)NC(C(=O)O1)C(C)C)C)CC(C)C)C |
| InChI | InChI=1S/C34H57N7O8/c1-9-21(7)28-33(47)40-23(11-10-12-35-40)32(46)41-26(15-22(42)16-36-41)30(44)38(8)25(13-18(2)3)31(45)39-17-20(6)14-24(39)29(43)37-27(19(4)5)34(48)49-28/h18-28,35-36,42H,9-17H2,1-8H3,(H,37,43) |
| InChI Key | LCPAGRQZIUUALQ-UHFFFAOYSA-N |
Properties
| Appearance | Flake Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Oxygen-terminated few-layered Ti3C2Tx MXene nanosheets as peroxidase-mimic nanozyme for colorimetric detection of kanamycin
Weizheng Wang, Yaoqi Yin, Sundaram Gunasekaran Biosens Bioelectron. 2022 Dec 15;218:114774. doi: 10.1016/j.bios.2022.114774. Epub 2022 Oct 2.
Nanomaterials-based bioinspired enzyme mimics are gaining increased attention as alternatives to biocatalysts. Herein, we report synthesizing oxygen-terminated few-layered titanium-based MXene nanosheets (OFL-Ti-MN). OFL-Ti-MN possesses horseradish peroxidase (HRP) activity in catalyzing the oxidation of colorless 3,3',5,5'-tetramethylbenzidine (TMB) in the presence of hydrogen peroxide (H2O2), which turns the solution color bluish-green. The solution color fades quickly when kanamycin (KAN) is added to this system. This reaction indicates that KAN can prevent color change in the OFL-Ti-MN/TMB-H2O2 system. Based on this strategy, we developed an OFL-Ti-MN-based colorimetric sensor to detect and quantify KAN. The sensor exhibited a dynamic range from 15.28 nM to 46.14 μM and a calculated limit of detection (LOD) of 15.28 nM. From the insight gained from the peroxidase-mimic property of OFL-Ti-MN, we proposed a mechanism for the inhibition effect of KAN on peroxidase and peroxidase-mimic enzymes. The proposed mechanism can potentially help elucidate the reasons for the antibacterial function of KAN and its side effects in humans.
2. Stepwise Post-glycosylation Modification of Sugar Moieties in Kanamycin Biosynthesis
Fumitaka Kudo, Yukinobu Kitayama, Akimasa Miyanaga, Mario Numakura, Tadashi Eguchi Chembiochem. 2021 May 4;22(9):1668-1675. doi: 10.1002/cbic.202000839. Epub 2021 Feb 11.
Kanamycin A is the major 2-deoxystreptamine (2DOS)-containing aminoglycoside antibiotic produced by Streptomyces kanamyceticus. The 2DOS moiety is linked with 6-amino-6-deoxy-d-glucose (6ADG) at O-4 and 3-amino-3-deoxy-d-glucose at O-6. Because the 6ADG moiety is derived from d-glucosamine (GlcN), deamination at C-2 and introduction of C-6-NH2 are required in the biosynthesis. A dehydrogenase, KanQ, and an aminotransferase, KanB, are presumed to be responsible for the introduction of C-6-NH2 , although the substrates have not been identified. Here, we examined the substrate specificity of KanQ to better understand the biosynthetic pathway. It was found that KanQ oxidized kanamycin C more efficiently than the 3''-deamino derivative. Furthermore, the substrate specificity of an oxygenase, KanJ, that is responsible for deamination at C-2 of the GlcN moiety was examined, and the crystal structure of KanJ was determined. It was found that C-6-NH2 is important for substrate recognition by KanJ. Thus, the modification of the GlcN moiety occurs after pseudo-trisaccharide formation, followed by the introduction of C-6-NH2 by KanQ/KanB and deamination at C-2 by KanJ.
3. Reusable molecularly imprinted electrochemiluminescence assay for kanamycin based on ordered mesoporous carbon loaded with indium oxide nanoparticles and carbon quantum dots
Shuhuai Li, Yuwei Wu, Chaohai Pang, Xionghui Ma, Mingyue Wang, Jinhui Luo, Xu Zhi, Bei Li Mikrochim Acta. 2022 Oct 26;189(11):431. doi: 10.1007/s00604-022-05527-8.
A highly sensitive kanamycin electrochemiluminescence (ECL) switch sensor was constructed. A signal element consisting of ordered mesoporous carbon loaded with indium oxide nanoparticles/carbon quantum dots (OMC/In2O3/C-dots) was assembled on the surface of a gold electrode. Then, a molecularly imprinted polymer (MIP) was prepared on the modified electrode surface using kanamycin as the template molecule and o-aminophenol as the functional monomer. After kanamycin elution, the prepared sensor retained specific kanamycin recognition sites. OMC/In2O3 effectively amplified the ECL signal of the C-dots, thereby enhancing the detection sensitivity, whereas kanamycin quenched the signal. Therefore, the imprinted sites acted as a switch, providing a new method for detecting kanamycin. Under the optimal experimental conditions, the concentration of kanamycin was proportional to the degree of ECL quenching within a linear range of 5-4500 × 10-12 mol L-1 at 0.8 V (vs. Ag/AgCl electrode electrode), and the detection limit was 5.8 × 10-13 mol L-1. When applied to the detection of kanamycin in actual samples, such as chicken, duck, pork, and milk, the recovery for spiked samples was in the range 92.7-110%.
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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 ╳
