kasugamycin
Sign in to saveAlso known as 3-O-[2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-alpha-D-arabino-hexopyranosyl]-D-chiro-inositol, Kasumin 2L, Kasumin L
Kasugamycin (Ksg) is an aminoglycoside antibiotic that was originally isolated in 1965, from Streptomyces kasugaensis, a Streptomyces strain found near the Kasuga shrine in Nara, Japan. Kasugamycin was discovered by Hamao Umezawa, who also discovered kanamycin and bleomycin, as a drug that prevent growth of a fungus causing rice blast disease. It was later found to inhibit bacterial growth also. It exists as a white, crystalline substance with the chemical formula C14H28ClN3O10 (kasugamycin hydrochloride). It is also known as kasumin.
Wikidata facts
- Mass
- 379.1591
Show 3 more facts
- chemical formula
- C₁₄H₂₅N₃O₉
- canonical SMILES
- CC1(C(CC(C(O1)(OC2(C(C(C(C(C2(O)[H])(O)[H])(O)[H])(O)[H])(O)[H])[H])[H])(N)[H])(N=C(C(O)=O)N)[H])[H]
- isomeric SMILES
- C[C@@]1([C@](C[C@@]([C@](O1)(O[C@]2([C@@]([C@]([C@]([C@@]([C@@]2(O)[H])(O)[H])(O)[H])(O)[H])(O)[H])[H])[H])(N)[H])(N=C(C(O)=O)N)[H])[H]
Sources (2)
via Wikidata · CC0
~5 min read
Article
5 sectionsContents
- Mechanism of action
- Structural basis for kasugamycin action
- Resistance
- References
- Further reading
Kasugamycin (Ksg) is an aminoglycoside antibiotic that was originally isolated in 1965, from Streptomyces kasugaensis, a Streptomyces strain found near the Kasuga shrine in Nara, Japan. Kasugamycin was discovered by Hamao Umezawa, who also discovered kanamycin and bleomycin, as a drug that prevent growth of a fungus causing rice blast disease. It was later found to inhibit bacterial growth also. It exists as a white, crystalline substance with the chemical formula C14H28ClN3O10 (kasugamycin hydrochloride). It is also known as kasumin.
==Mechanism of action== Like many of the known natural antibiotics, kasugamycin inhibits proliferation of bacteria by tampering with their ability to make new proteins, the ribosome being the major target. Kasugamycin inhibits protein synthesis at the step of translation initiation. Kasugamycin inhibition is thought to occur by direct competition with initiator transfer RNA. Recent experiments suggest that kasugamycin indirectly induces dissociation of P-site-bound fMet-tRNAfMet from 30S subunits through perturbation of the mRNA, thereby interfering with translation initiation.