1147358-80-2

Basic information

• Product Name: 2',3',4',2'',4'',6''-O-hexaacetyl-1,3,6',3''-tetraazido-kanamycin A
• Synonyms: 2',3',4',2'',4'',6''-O-hexaacetyl-1,3,6',3''-tetraazido-kanamycin A
• CAS NO: 1147358-80-2
• Molecular Weight: 840.718
• Mol File: 1147358-80-2.mol

Chemical Properties

• CAS DataBase Reference: 2',3',4',2'',4'',6''-O-hexaacetyl-1,3,6',3''-tetraazido-kanamycin A(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3',4',2'',4'',6''-O-hexaacetyl-1,3,6',3''-tetraazido-kanamycin A(1147358-80-2)
• EPA Substance Registry System: 2',3',4',2'',4'',6''-O-hexaacetyl-1,3,6',3''-tetraazido-kanamycin A(1147358-80-2)

Safety Data

• Hazardous Substances Data: 1147358-80-2(Hazardous Substances Data)

Upstream product

• 59-01-8 kanamycin A 
• 1037515-73-3 1,3,6',3”-tetra-azido-kanamycin A 
• 108-24-7 acetic anhydride 

Downstream Products

• 1224197-10-7 C₄₁H₅₄N₁₂O₂₄ 
• 1037515-73-3 1,3,6',3”-tetra-azido-kanamycin A 
• 20744-51-8 6-O-[(3-deoxy-3-amino)-α-D-glucopyranosyl]-2-deoxy-streptamine 

Relevant articles and documents

Effects of 5-O-Ribosylation of Aminoglycosides on Antimicrobial Activity and Selective Perturbation of Bacterial Translation

We studied six pairs of aminoglycosides and their corresponding ribosylated derivatives synthesized by attaching a β-O-linked ribofuranose to the 5-OH of the deoxystreptamine ring of the parent pseudo-oligosaccharide antibiotic. Ribosylation of the 4,6-disubstituted 2-deoxystreptamine aminoglycoside kanamycin B led to improved selectivity for inhibition of prokaryotic relative to cytosolic eukaryotic in vitro translation. For the pseudodisaccharide aminoglycoside scaffolds neamine and nebramine, ribosylated derivatives were both more potent antimicrobials and more selective to inhibition of prokaryotic translation. On the basis of the results of this study, we suggest that modification of the 5-OH position of the streptamine ring of other natural or semisynthetic pseudodisaccharide aminoglycoside scaffolds containing an equatorial amine at the 2′ sugar position with a β-O-linked ribofuranose is a promising avenue for the development of novel aminoglycoside antibiotics with improved efficacy and reduced toxicity.

Synthesis of ring II/III fragment of Kanamycin: A new minimum structural motif for aminoglycoside recognition

A novel protocol has been established to prepare the kanamycin ring II/III fragment, which has been validated as a minimum structural motif for the development of new aminoglycosides on the basis of its bactericidal activity even against resistant strains. Furthermore, its ability to act as a AAC-(6′) and APH-(3′) binder, and as a poor substrate for the ravenous ANT-(4′), makes it an excellent candidate for the design of inhibitors of these aminoglycoside modifying enzymes.

Structure-based design of highly crowded ribostamycin/kanamycin hybrids as a new family of antibiotics

Sugar sugar! The synthesis and evaluation of ribostamycin/kanamycin hybrids incorporating a highly crowded trisubstituted aminocyclitol unit that should provide maximum complementation with the RNA receptor are reported (see picture). Analysis shows that the existing conflicts between the different sugar rings can be significantly alleviated by a simple chemical modification, leading to an improvement in activity. (Figure Presented)