Kasugamycin hydrochloride
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| Category | Antibiotics |
| Catalog number | BBF-03848 |
| CAS | 19408-46-9 |
| Molecular Weight | 415.82 |
| Molecular Formula | C14H26ClN3O9 |
| Purity | ≥73.5% |
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Description
Kasugamycin hydrochloride is an aminoglycoside antibiotic produced by Streptomyces. It is a broad spectrum antifungal used against yeast and pathogenic fungi such as M. Grisea.
Specification
| Related CAS | 6980-18-3 (free base) 11014-57-6 (Deleted CAS) 12609-82-4 (Deleted CAS) 39080-40-5 (Deleted CAS) 1135443-65-0 (Deleted CAS) |
| Synonyms | D-chiro-Inositol, 3-O-[2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranosyl]-, hydrochloride (1:1); D-chiro-Inositol, 3-O-[2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranosyl]-, monohydrochloride; Kasugamycin, monohydrochloride; Kasumin |
| Storage | Store at -20°C |
| IUPAC Name | 2-amino-2-[(2R,3S,5S,6R)-5-amino-2-methyl-6-[(2S,3S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyoxan-3-yl]iminoacetic acid;hydrochloride |
| Canonical SMILES | Cl.O=C(O)C(=N)NC1CC(N)C(OC1C)OC2C(O)C(O)C(O)C(O)C2O |
| InChI | InChI=1S/C14H25N3O9.ClH/c1-3-5(17-12(16)13(23)24)2-4(15)14(25-3)26-11-9(21)7(19)6(18)8(20)10(11)22;/h3-11,14,18-22H,2,15H2,1H3,(H2,16,17)(H,23,24);1H/t3-,4+,5+,6-,7+,8+,9-,10+,11+,14-;/m1./s1 |
| InChI Key | ZDRBJJNXJOSCLR-NZXABURVSA-N |
Properties
| Appearance | White Crystalline Powder |
| Antibiotic Activity Spectrum | Fungi; yeast |
| Melting Point | 202-204°C (dec.) |
| Solubility | Soluble in Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly) |
Reference Reading
1.Synthesis, characterization, and application of microbe-triggered controlled-release kasugamycin-pectin conjugate.
Liu Y1, Sun Y1, Ding G1, Geng Q1, Zhu J1, Guo M1, Duan Y1, Wang B1, Cao Y1. J Agric Food Chem. 2015 May 6;63(17):4263-8. doi: 10.1021/jf5055062. Epub 2015 Apr 27.
The controlled and targeted release of pesticides with high water solubility has been a challenge for integrated pest management. In this paper, kasugamycin, an antibiotic broadly used in plant disease control, was covalently conjugated to pectin to form a kasugamycin-pectin conjugate by an amide bond. The conjugate was structurally characterized by Fourier transform infrared spectroscopy, ultraviolet spectrophotometry, and thermal gravimetric analysis. The results showed that the conjugate was stable over a wide range of pH and temperatures, as well as under UV irradiation. When incubated with Pseudomonas syringae pv. lachrymans, the conjugate could be activated, releasing the kasugamycin, which made it a promising controlled-release formulation of pesticide.
2.Characterization of the microbial community structure in Candidatus Liberibacter asiaticus-infected citrus plants treated with antibiotics in the field.
Zhang M1, Powell CA, Guo Y, Benyon L, Duan Y. BMC Microbiol. 2013 May 23;13:112. doi: 10.1186/1471-2180-13-112.
BACKGROUND: Huanglongbing (HLB) is a worldwide devastating disease of citrus. There are no effective control measures for this newly emerging but century-old disease. Previously, we reported a combination of Penicillin G and Streptomycin was effective in eliminating or suppressing the associated bacterium, 'Candidatus Liberibacter asiaticus' (Las).
3.(p)ppGpp-dependent and -independent pathways for salt tolerance in Escherichia coli.
Tarusawa T1, Ito S1, Goto S1, Ushida C1, Muto A1, Himeno H2. J Biochem. 2016 Jan 27. pii: mvw008. [Epub ahead of print]
Addition of some kinds of translation inhibitors targeting the ribosome such as kasugamycin to the culture medium as well as removal of a ribosome maturation factor or a ribosomal protein provides Escherichia coli cells with tolerance to high salt stress. Here, we found that another kind of translation inhibitor, serine hydroxamate (SHX), which induces amino acid starvation leading to (p)ppGpp production, also has a similar effect, but via a different pathway. Unlike kasugamycin, SHX was not effective in (p)ppGpp-null mutant cells. SHX and depletion of RsgA, a ribosome maturation factor, had an additive effect on salt tolerance, while kasugamycin or depletion of RsgA did not. These results indicate the presence of two distinct pathways, (p)ppGpp-dependent and -independent pathways, for salt tolerance of E. coli cell. Both pathways operate even in the absence of σS, an alternative sigma factor involved in the stationary phase or stress response.
4.Dimethyl adenosine transferase (KsgA) deficiency in Salmonella enterica Serovar Enteritidis confers susceptibility to high osmolarity and virulence attenuation in chickens.
Chiok KL1, Addwebi T, Guard J, Shah DH. Appl Environ Microbiol. 2013 Dec;79(24):7857-66. doi: 10.1128/AEM.03040-13. Epub 2013 Oct 11.
Dimethyl adenosine transferase (KsgA) performs diverse roles in bacteria, including ribosomal maturation and DNA mismatch repair, and synthesis of KsgA is responsive to antibiotics and cold temperature. We previously showed that a ksgA mutation in Salmonella enterica serovar Enteritidis results in impaired invasiveness in human and avian epithelial cells. In this study, we tested the virulence of a ksgA mutant (the ksgA::Tn5 mutant) of S. Enteritidis in orally challenged 1-day-old chickens. The ksgA::Tn5 mutant showed significantly reduced intestinal colonization and organ invasiveness in chickens compared to those of the wild-type (WT) parent. Phenotype microarray (PM) was employed to compare the ksgA::Tn5 mutant and its isogenic wild-type strain for 920 phenotypes at 28°C, 37°C, and 42°C. At chicken body temperature (42°C), the ksgA::Tn5 mutant showed significantly reduced respiratory activity with respect to a number of carbon, nitrogen, phosphate, sulfur, and peptide nitrogen nutrients.
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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 ╳
