Structure via PubChem · Public domain (PubChem)
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.
In the Vinony graph
Within Vinony's link graph, kasugamycin is referenced by 6 other articles, and connects out to Japan, protein and International Standard Book Number.
It sits within the topics Aminoglycoside antibiotics, Chembox image size set and Chemical articles with multiple CAS registry numbers.
Its subject is documented across 8 Wikipedia language editions.
Chemical data
- Formula
- C14H25N3O9
- Molecular weight
- 379.36 g/mol
- IUPAC name
- 2-amino-2-[(2R,3S,5S,6R)-5-amino-2-methyl-6-[(2R,3S,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxyoxan-3-yl]iminoacetic acid
- SMILES
- C[C@@H]1[C@H](C[C@@H]([C@H](O1)OC2[C@@H]([C@H](C([C@@H]([C@@H]2O)O)O)O)O)N)N=C(C(=O)O)N
- InChIKey
- PVTHJAPFENJVNC-UQTMRZPGSA-N
- XLogP
- -6.7
- Polar surface area
- 221 Ų
- H-bond donors
- 8
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
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
Encyclopedic overview
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.
Excerpted from Wikipedia’s “kasugamycin” article, available under the CC BY-SA 4.0 licence.