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K4013

Sigma-Aldrich

Kasugamycin hydrochloride from Streptomyces kasugaensis

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Synonym(s):
3-O-[2-Amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-D-arabino-hexopyranosyl]-D-chiro-inositol
Empirical Formula (Hill Notation):
C14H25N3O9 · HCl
CAS Number:
19408-46-9
Molecular Weight:
415.82
MDL number:
MFCD00058459
UNSPSC Code:
51101500
PubChem Substance ID:
24896238
NACRES:
NA.85

biological source

Streptomyces kasugaensis

Quality Level

200

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.

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

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Ceshing Sheu et al.
Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes, 45(5), 478-484 (2010-06-01)
A high performance liquid chromatographic (HPLC) analysis method with an ultraviolet (UV) detector and an Aqua C18 (250 x 4.6 mm, Phenomenex) column were applied to analyze the antibiotic fungicide kasugamycin in water. An aromatic sulfonic acid spe column (Backerbond
Atsushi Yoshii et al.
Applied and environmental microbiology, 78(16), 5555-5564 (2012-06-05)
Kasugamycin (KSM), a unique aminoglycoside antibiotic, has been used in agriculture for many years to control not only rice blast caused by the fungus Magnaporthe grisea but also rice bacterial grain and seedling rot or rice bacterial brown stripe caused
Koichi Inoue et al.
Journal of bacteriology, 189(23), 8510-8518 (2007-09-25)
A 16S rRNA methyltransferase, KsgA, identified originally in Escherichia coli is highly conserved in all living cells, from bacteria to humans. KsgA orthologs in eukaryotes possess functions in addition to their rRNA methyltransferase activity. E. coli Era is an essential
Reiko Amikura et al.
Mechanisms of development, 122(10), 1087-1093 (2005-08-30)
In Drosophila, mitochondrially encoded ribosomal RNAs (mtrRNAs) form mitochondrial-type ribosomes on the polar granules, distinctive organelles of the germ plasm. Since a reduction in the amount of mtrRNA results in the failure of embryos to produce germline progenitors, or pole
Jeffrey Sabina et al.
Journal of bacteriology, 185(20), 6158-6170 (2003-10-04)
Escherichia coli responses to four inhibitors that interfere with translation were monitored at the transcriptional level. A DNA microarray method provided a comprehensive view of changes in mRNA levels after exposure to these agents. Real-time reverse transcriptase PCRanalysis served to
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