20744-51-8

Usage

Uses

Used in Pharmaceutical Industry:
TOBRAMYCIN A is used as an antibacterial agent for the treatment of various bacterial infections. Its application is primarily due to its ability to inhibit bacterial growth and proliferation, making it a valuable component in the development of antibiotics.
Used in Research and Development:
In addition to its pharmaceutical applications, TOBRAMYCIN A is also utilized in research and development for the study of antibiotic properties, mechanisms of action, and potential improvements or modifications to enhance its efficacy and reduce side effects.

InChI:InChI=1/C12H25N3O7/c13-3-1-4(14)11(10(20)7(3)17)22-12-9(19)6(15)8(18)5(2-16)21-12/h3-12,16-20H,1-2,13-15H2/t3-,4+,5+,6-,7+,8+,9+,10-,11-,12+/m0/s1

Upstream product

• 144218-67-7 3',4'-anhydro-6'-N-(benzyloxycarbonyl)-4'-epi-1,3,3''-tri-N-tosylkanamycin A 
• 179533-32-5 6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine 
• 1147358-80-2 2',3',4',2'',4'',6''-O-hexaacetyl-1,3,6',3''-tetraazido-kanamycin A 
• 1037515-73-3 1,3,6',3”-tetra-azido-kanamycin A 
• 59-01-8 kanamycin A 
• 3847-27-6 Kanamycin A sulfate 
• 144218-66-6 2''-O-acetyl-6'-N-(benzyloxycarbonyl)-4'-O-(benzylsulfonyl)-1,3,3''-tri-N-tosylkanamycin A 
• 179533-31-4 1,3,6',3''-tetra-N-tosylkanamycin A 
• 179533-33-6 6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-4-O-(6-azido-3-oxa-2,3,4,6-tetradeoxy-α-D-glycero-hexopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine 
• 133-92-6 kanamycin A sulfate 
• 103358-05-0 2-deoxy-6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-1,3-di-N-tosylstreptamine 
• 144218-74-6 6-O-(4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine 

Downstream Products

• 22860-83-9 (1S)-N,N'-diacetyl-O⁴-(3-acetylamino-3-deoxy-α-D-glucopyranosyl)-2-deoxy-streptamine 

Relevant academic research and scientific papers

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.

Synthesis of kanamycin A analogs containing 6-amino-3-oxa-2,3,4,6-tetradeoxy-D- and -L-glycero-hexopyranose

6-Azido-3-oxa-2,3,4,6-tetradeoxy-D- and -L-glycero-hexopyranoses were synthesized in five steps from (2S)- and (2R)-1,2-O-isopropylideneglycerols, respectively. After conversion into the corresponding ethyl 1-thioglycosides, each was condensed with a protected derivative of 6-O-(3-amino-3-deoxy-α-D-glucopyranosyl)-2-deoxystreptamine (16). Deprotection and reduction of the azido group of the condensation products gave the title compounds.

Synthesis of 4'-deoxy-4'-fluorokanamycin A and B

4'-Deoxy-4'-fluorokanamycins A (17) and B (25) have been prepared through fluorinating ring-opening of the D-galacto-3',4'-oxiranes (8 and 21) derived from kanamycin A and B with potassium hydrogenfluoride in ethane-1,2-diol.The mechanism of preponderant formation of the 4'-deoxy-4'-fluoro-D-gluco ( 9 and 22) over the 3'-deoxy-3'-fluoro-D-gulo derivatives was discussed.In the synthesis of 25, the unusual 3',6'-epimine (23) was the main product along with the 4'-deoxy-4'-fluoro derivative.The mechanism of this reaction is also discussed.Both 17 and 25 were active against resistant bacteria producing aminoglycoside-adenylylating enzymes for HO-4'.