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K4013

Sigma-Aldrich

Kasugamycin hydrochloride from Streptomyces kasugaensis

Synonym(s):

3-O-[2-Amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-D-arabino-hexopyranosyl]-D-chiro-inositol

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About This Item

Empirical Formula (Hill Notation):
C14H25N3O9 · HCl
CAS Number:
19408-46-9
Molecular Weight:
415.82
MDL number:
MFCD00058459
UNSPSC Code:
51102829
PubChem Substance ID:
24896238
NACRES:
NA.85

biological source

Streptomyces kasugaensis

form

powder

color

white to off-white

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

C[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H](N)C[C@@H]1NC(C(O)=O)=N.Cl

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

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General description

Chemical structure: aminoglycoside

Application

Kasugamycin (Ksg) is an aminoglycoside antibiotic isolated from Streptomyces kasugaensis. It is used to study ribosome structure and interactions near the m26A m26A sequence. It is used to study the mechanisms of kasugamycin resistance.

Biochem/physiol Actions

Kasugamycin binds within the mRNA channel of the 30S subunit between the universally conserved G926 and A794 nucleotides in 16S ribosomal RNA. It inhibits protein synthesis and binding of aminoacyl-sRNA to the ribosomes in fungi and induces f-met-tRNA dissociation from the P-site of the 30S subunit.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tamara Zarubica et al.
RNA (New York, N.Y.), 17(2), 346-355 (2010-12-24)
Bacterial resistance to 4,6-type aminoglycoside antibiotics, which target the ribosome, has been traced to the ArmA/RmtA family of rRNA methyltransferases. These plasmid-encoded enzymes transfer a methyl group from S-adenosyl-L-methionine to N7 of the buried G1405 in the aminoglycoside binding site
P Thammana et al.
Nucleic acids research, 5(3), 805-823 (1978-03-01)
Antibodies raised against N6, N6-dimethyl adenosine were used to study the environment and role of the m62Am62A sequences in the E. coli ribosome. It is observed that this sequence is exposed on the surface of isolated 30S subunits, but becomes
Chi-Yu Huang et al.
Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes, 45(5), 485-491 (2010-06-01)
The degradation of kasugamycin in water and the effects of kasugamycin on the bacterial communities in sediment and overlying water were analyzed over a 30-day period. Kasugamycin is generally regarded as nontoxic to microorganisms, but in this study we demonstrated
Gayle C McGhee et al.
Phytopathology, 101(2), 192-204 (2010-10-07)
The emergence and spread of streptomycin-resistant strains of Erwinia amylovora in Michigan has necessitated the evaluation of new compounds effective for fire blight control. The aminoglycoside antibiotic kasugamycin (Ks) targets the bacterial ribosome and is particularly active against E. amylovora.
Paul M Duffin et al.
International journal of antimicrobial agents, 33(4), 321-327 (2008-12-23)
The aminoglycoside antibiotic kasugamycin (KSG) inhibits translation initiation and thus the growth of many bacteria. In this study, we tested the susceptibilities to KSG of 22 low-passage clinical isolates and 2 laboratory strains of Neisseria gonorrhoeae. Although the range of
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