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A2024

Sigma-Aldrich

Apramycin sulfate salt

Synonym(s):

Nebramycin II

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About This Item

Empirical Formula (Hill Notation):
C21H41N5O11 · xH2SO4
CAS Number:
65710-07-8
Molecular Weight:
539.58 (free base basis)
EC Number:
265-890-7
MDL number:
MFCD06200257
UNSPSC Code:
51281633
PubChem Substance ID:
329770728
NACRES:
NA.85

biological source

Streptomyces tenebrarius

Quality Level

200

form

powder

color

white to brown

antibiotic activity spectrum

Gram-negative bacteria

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

OS(O)(=O)=O.CN[C@H]1[C@@H](O)[C@H]2O[C@H](O[C@@H]3[C@@H](N)C[C@@H](N)[C@H](O)[C@H]3O)[C@H](N)C[C@@H]2O[C@@H]1O[C@H]4O[C@H](CO)[C@@H](N)[C@H](O)[C@H]4O

InChI

1S/C21H41N5O11.H2O4S/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31;1-5(2,3)4/h5-21,26-32H,2-4,22-25H2,1H3;(H2,1,2,3,4)/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-;/m1./s1

InChI key

WGLYHYWDYPSNPF-RQFIXDHTSA-N

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General description

Chemical structure: aminoglycoside

Application

Apramycin is used to study antibiotic resistance as well as protein synthesis translocation-step inhibition in bacteria and prokaryotes.

Biochem/physiol Actions

Apramycin inhibits protein synthesis by blocking translocation. It is also able to bind to the eukaryotic decoding site. At low concentrations it inhibits elongation and induces misreading of mRNA during protein synthesis.

Packaging

1G, 5G

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.Storage class (TRGS 510): Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360FD

Hazard Classifications

Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000395317
0000356526
0000356526
0000380005
0000334301

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Mingxuan Xu et al.
Science in China. Series C, Life sciences, 49(4), 362-369 (2006-09-23)
Apramycin is unique in the aminoglycoside family due to its octodiose moiety. However, either the biosynthesis process or the precursors involved are largely unknown. Addition of glycine, as well as serine or threonine, to the Streptomyces tenebrabrius UD2 fermentation medium
R Doug Wagner et al.
Antimicrobial agents and chemotherapy, 52(4), 1230-1237 (2008-01-30)
A bioassay was developed to measure the minimum concentration of an antimicrobial drug that disrupts the colonization resistance mediated by model human intestinal microbiota against Salmonella invasion of Caco-2 intestinal cells. The bioassay was used to measure the minimum disruptive
Tanja Matt et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(27), 10984-10989 (2012-06-16)
Aminoglycosides are potent antibacterials, but therapy is compromised by substantial toxicity causing, in particular, irreversible hearing loss. Aminoglycoside ototoxicity occurs both in a sporadic dose-dependent and in a genetically predisposed fashion. We recently have developed a mechanistic concept that postulates
Serena Bernacchi et al.
Nucleic acids research, 35(21), 7128-7139 (2007-10-19)
Owing to a striking, and most likely fortuitous, structural and sequence similarity with the bacterial 16 S ribosomal A site, the RNA kissing-loop complex formed by the HIV-1 genomic RNA dimerization initiation site (DIS) specifically binds 4,5-disubstituted 2-deoxystreptamine (2-DOS) aminoglycoside
Jiro Kondo et al.
Chembiochem : a European journal of chemical biology, 8(14), 1700-1709 (2007-08-21)
The lack of absolute prokaryotic selectivity of natural antibiotics is widespread and is a significant clinical problem. The use of this disadvantage of aminoglycoside antibiotics for the possible treatment of human genetic diseases is extremely challenging. Here, we have used
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