289505-10-8

Basic information

• Product Name: (2R,3S,4R,5R,6S)-5-azido-6-(((1R,2R,3S,4R,6S)-4, 6-diazido-2,3-dihydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol
• Synonyms: (2R,3S,4R,5R,6S)-5-azido-6-(((1R,2R,3S,4R,6S)-4, 6-diazido-2,3-dihydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol
• CAS NO: 289505-10-8
• Molecular Weight: 401.339
• Mol File: 289505-10-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (2R,3S,4R,5R,6S)-5-azido-6-(((1R,2R,3S,4R,6S)-4, 6-diazido-2,3-dihydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4R,5R,6S)-5-azido-6-(((1R,2R,3S,4R,6S)-4, 6-diazido-2,3-dihydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol(289505-10-8)
• EPA Substance Registry System: (2R,3S,4R,5R,6S)-5-azido-6-(((1R,2R,3S,4R,6S)-4, 6-diazido-2,3-dihydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol(289505-10-8)

Safety Data

• Hazardous Substances Data: 289505-10-8(Hazardous Substances Data)

Upstream product

• 7205-49-4 paromomycin sulfate 
• 7542-37-2 paromomycin 
• 534-47-4 Paromamine 

Downstream Products

• 289505-11-9 Acetic acid (1S,2S,3R,4S,6R)-4,6-diazido-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyl ester 
• 918800-23-4 (1S,2R,3R,4S,6R)-4,6-Diamino-3-((2S,3R,4S,5S,6R)-3,4-diamino-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol 
• 918800-42-7 (1S,2R,3R,4S,6R)-4,6-Diazido-3-((2S,3R,4S,5S,6R)-3,4-diazido-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol 
• 918800-29-0 Benzoic acid (2S,3R,4R,5S,6R)-3-azido-2-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester 
• 918800-21-2 (2R,3R,4S,5R)-2-[(2S,3R,4R,5S,6R)-3-Amino-2-((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 918800-19-8 NB₃₀ 
• 918800-20-1 (2R,3S,4R,5R,6S)-5-Amino-6-[(1R,2S,3S,4R,6S)-4,6-diamino-3-((2S,3R,4S,5R)-5-aminomethyl-3,4-dihydroxy-tetrahydro-furan-2-yloxy)-2-hydroxy-cyclohexyloxy]-2-hydroxymethyl-tetrahydro-pyran-3,4-diol 
• 918800-22-3 (2S,3R,4S,5R)-2-[(2S,3R,4R,5S,6R)-3-Amino-2-((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-5-aminomethyl-tetrahydro-furan-3,4-diol 
• 918800-26-7 Benzoic acid (2R,4aR,6S,7R,8R,8aS)-7-azido-6-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 918800-39-2 (2R,3R,4S,5R)-2-[(2S,3R,4R,5S,6R)-3-Azido-2-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 918800-38-1 (2S,3R,4S,5R)-2-[(2S,3R,4R,5S,6R)-3-Azido-2-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-5-azidomethyl-tetrahydro-furan-3,4-diol 
• 918800-40-5 (2R,3S,4R,5R,6S)-5-Azido-6-[(1R,2S,3S,4R,6S)-4,6-diazido-3-((2S,3R,4S,5R)-5-azidomethyl-3,4-dihydroxy-tetrahydro-furan-2-yloxy)-2-hydroxy-cyclohexyloxy]-2-hydroxymethyl-tetrahydro-pyran-3,4-diol 
• 952052-48-1 C₃₁H₃₄N₁₂O₁₂ 
• 952052-47-0 C₃₈H₃₉N₉O₁₄ 

Relevant articles and documents

Exploring eukaryotic: Versus prokaryotic ribosomal RNA recognition with aminoglycoside derivatives

New derivatives of aminoglycosides containing 6′-carboxylic acid or 6′-amide on their ring I were designed, synthesized and their ability to readthrough nonsense mutations was examined in vitro, along with the protein translation inhibition in prokaryotic and eukaryotic systems. The observed structure-activity relationships, along with the comparative molecular dynamics simulations within the eukaryotic rRNA decoding site, showed high sensitivity of 6′-position to substitution, indicating that the rational design of potent stop-codon read-through inducers requires consideration of not only the structure and energetics of the drug-RNA interaction but also the dynamics associated with that interaction.

Towards Catalytic Antibiotics: Redesign of Aminoglycosides To Catalytically Disable Bacterial Ribosomes

The emergence of multidrug-resistant pathogens that are resistant to the majority of currently available antibiotics is a significant clinical problem. The development of new antibacterial agents and novel approaches is therefore extremely important. We set out to explore the potential of catalytic antibiotics as a new paradigm in antibiotics research. Herein, we describe our pilot study on the design, synthesis, and biological testing of a series of new derivatives of the natural aminoglycoside antibiotic neomycin B for their potential action as catalytic antibiotics. The new derivatives showed significant antibacterial activity against wild-type bacteria and were especially potent against resistant and pathogenic strains including Pseudomonas aeruginosa and methicillin-resistant Staphylococcus aureus. Selected compounds displayed RNase activity even though the activity was not as high and specific as we would have expected. On the basis of the observed chemical and biochemical data, along with the comparative molecular dynamics simulations of the prokaryotic rRNA decoding site, we postulate that the rational design of catalytic antibiotics should involve not only their structure but also a comprehensive analysis of the rRNA A-site dynamics.

NOVEL AMINOGLYCOSIDES AND USES THEREOF IN THE TREATMENT OF GENETIC DISORDERS

A new class of paromomycin-derived aminoglycosides, which exhibit efficient stop-codon mutation suppression activity, low cytotoxicity and selectivity towards eukaryotic cells are provided. Also provided are processes of preparing these paromomycin-derived aminoglycosides and intermediates thereof, as well as pharmaceutical compositions containing the same, and uses thereof in the treatment of genetic disorders.