688744-66-3

Upstream product

• 182554-04-7 1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine 
• 474266-81-4 hexaazido-hepta-O-acetyl neomycin 
• 108-24-7 acetic anhydride 
• 671809-10-2 1,3,2′,6′-tetraazidoneamine 
• 468065-21-6 hexaazidoneomycin B 
• 119-04-0 neomycin B 
• 3947-65-7 neomycin A 
• 688744-65-2 1,3,2’,6’-tetrazido-5,6-O-cyclohexylidene neamine 
• 15446-43-2 neamine tetrahydrochloride 

Downstream Products

• 1241744-82-0 C₂₉H₃₄N₁₂O₁₂ 
• 1383687-49-7 3',4'-di-O-acetyl-5-[[(propylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-50-0 3',4'-di-O-acetyl-6-[[( propylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-51-1 5-[[(propylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-52-2 6-[[(propylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-55-5 5-[[(3-azidopropylamino)carbonyl]oxy]-3',4'-di-O-acetyl-1,3,2',6'-tetraazidoneamine 
• 1383687-56-6 6-[[(3-azidopropylamino)carbonyl]oxy]-3',4'-di-O-acetyl-1,3,2',6'-tetraazidoneamine 
• 1383687-57-7 5-[[(3-azidopropylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-58-8 6-[[(3-azidopropylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-61-3 6-[[(3-azidohexylamino)carbonyl]oxy]-3',4'-di-O-acetyl-1,3,2',6'-tetraazidoneamine 
• 1383687-60-2 5-[[(3-azidohexylamino)carbonyl]oxy]-3',4'-di-O-acetyl-1,3,2',6'-tetraazidoneamine 
• 1383687-63-5 6-[[(3-azidohexylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-62-4 5-[[(3-azidohexylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 

Relevant academic research and scientific papers

Synthesis of glycosidic (β-1′′→6, 3′ and 4′) site isomers of neomycin B and their effect on RNA and DNA triplex stability

Glycosidic (β-1′′→6, 3′ and 4′) site isomers of neomycin B (i.e., neobiosamine (β-1′′→6, 3′ and 4′) neamines) have been synthesized in a straightforward manner. Peracetylated neomycin azide was used as a common starting material to obtain neobiosamine glycosyl donor and 6, 3′,4′-tri-O-acetyl neamine azide that after simple protecting group manipulation was converted to three different glycosyl acceptors (i.e., 5,6,4′-, 5,3′,4′- and 5,6,3′-tri-O-acetyl neamine azide). Glycosylation between the neobiosamine glycosyl donor and the neamine-derived acceptors gave the protected pseudo-tetrasaccharides, which were converted, via global deprotection (deacetylation and reduction of the azide groups), to the desired site isomers of neomycin. The effect of these aminoglycosides on the RNA and DNA triplex stability was studied by UV-melting profile analysis.

Synthesis and antibacterial activity of novel neamine derivatives: Preponderant role of the substituent position on the neamine core

A series of neamine derivatives were prepared from the cyclic carbonate and sulfate of 1,3,2′,6′-tetraazido-3′,4′,-di-O- acetylneamine. Ring opening reactions with diversely substituted amines result in the formation of the corresponding carbamates or sulfonic acids with good overall yields. The antibacterial activities of the synthesized products against E. coli (DH5α) and S. aureus (RN4220) were evaluated. With isolated single regioisomers, the preponderant effect of the 5-positions of the carbamate substituent on the neamine core was demonstrated.

Application of glycodiversification: Expedient synthesis and antibacterial evaluation of a library of kanamycin B analogues

The expedient synthesis of a library of kanamycin B analogues is reported. The revealed SAR will guide future designs in developing kanamycin-type aminoglycoside antibiotics against drug-resistant bacteria.