54230-72-7

Basic information

• Product Name: {(1R,2S,3R,4R,5S)-5-tert-Butoxycarbonylamino-4-[(2R,3R,4R,5S,6R)-3-tert-butoxycarbonylamino-6-(tert-butoxycarbonylamino-methyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2,3-dihydroxy-cyclohexyl}-carbamic acid tert-butyl ester
• CAS NO: 54230-72-7
• Molecular Weight: 722.831
• Mol File: 54230-72-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: {(1R,2S,3R,4R,5S)-5-tert-Butoxycarbonylamino-4-[(2R,3R,4R,5S,6R)-3-tert-butoxycarbonylamino-6-(tert-butoxycarbonylamino-methyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2,3-dihydroxy-cyclohexyl}-carbamic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: {(1R,2S,3R,4R,5S)-5-tert-Butoxycarbonylamino-4-[(2R,3R,4R,5S,6R)-3-tert-butoxycarbonylamino-6-(tert-butoxycarbonylamino-methyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2,3-dihydroxy-cyclohexyl}-carbamic acid tert-butyl ester(54230-72-7)
• EPA Substance Registry System: {(1R,2S,3R,4R,5S)-5-tert-Butoxycarbonylamino-4-[(2R,3R,4R,5S,6R)-3-tert-butoxycarbonylamino-6-(tert-butoxycarbonylamino-methyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2,3-dihydroxy-cyclohexyl}-carbamic acid tert-butyl ester(54230-72-7)

Safety Data

• Hazardous Substances Data: 54230-72-7(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 15446-43-2 neamine tetrahydrochloride 

Downstream Products

• 1203670-10-3 C₆₀H₇₈N₈O₁₈ 
• 312957-79-2 3'-O-(6''-bromohexyl)-4'-O-benzyl-5,6-O-cyclohexylidene-tetra-N-benzyl-tetra-N-tert-butoxycarbonylneamine 
• 312957-78-1 1,3,2',6'-tetra-N-benzyl-4'-O-benzyl-1,3,2',6'-tetra-N-tert-butoxycarbonyl-3'-O-(5''-bromopentyl)-5,6-O-cyclohexylideneneamine 
• 312957-76-9 1,3,2',6'-tetra-N-benzyl-4'-O-benzyl-1,3,2',6'-tetra-N-tert-butoxycarbonyl-3'-O-tert-butyldimethylsilyl-5,6-O-cyclohexylideneneamine 
• 312957-60-1 1,3,2',6'-tetra-N-benzyl-3'-O-(8''-bromooctyl)-1,3,2'-tri-N-tert-butoxycarbonyl-6'-N,4'-O-carbonyl-5,6-O-cyclohexylideneneamine 
• 312957-59-8 1,3,2',6'-tetra-N-benzyl-3'-O-(7''-bromoheptyl)-1,3,2'-tri-N-tert-butoxycarbonyl-6'-N,4'-O-carbonyl-5,6-O-cyclohexylideneneamine 
• 312957-77-0 1,3,2',6'-tetra-N-benzyl-4'-O-benzyl-1,3,2',6'-tetra-N-tert-butoxycarbonyl-5,6-O-cyclohexylideneneamine 
• 312957-58-7 1,3,2',6'-tetra-N-benzyl-3'-O-(6''-bromohexyl)-1,3,2'-tri-N-tert-butoxycarbonyl-6'-N,4'-O-carbonyl-5,6-O-cyclohexylideneneamine 
• 312957-57-6 1,3,2',6'-tetra-N-benzyl-3'-O-(5''-bromopentyl)-1,3,2'-tri-N-tert-butoxycarbonyl-6'-N,4'-O-carbonyl-5,6-O-cyclohexylideneneamine 
• 312957-54-3 1,3,2',6'-tetra-N-benzyl-1,3,2'-tri-N-tert-butoxycarbonyl-3'-O-tert-butyldimethylsilyl-6'-N,4'-O-carbonyl-5,6-O-cyclohexylideneneamine 
• 312957-56-5 1,3,2',6'-tetra-N-benzyl-1,3,2'-tri-N-tert-butoxycarbonyl-6'-N,4'-O-carbonyl-5,6-O-cyclohexylideneneamine 

Relevant articles and documents

Tethered bisubstrate derivatives as probes for mechanism and as inhibitors of aminoglycoside 3'-phosphotransferases

Aminoglycoside 3'-phosphotransferases [APH(3')s] phosphorylate aminoglycoside antibiotics, a reaction that inactivates the antibiotics. These enzymes are the primary cause of resistance to aminoglycosides in bacteria. APH(3')-Ia operates by a random-equilibrium BiBi mechanism, whereas APH(3')-IIIa catalyzes its reaction by the Theorell-Chance mechanism, a form of ordered BiBi mechanism. Hence, both substrates have to be present in the active site prior to the transfer of phosphate by both mechanisms. Four bisubstrate analogues, compounds 1 - 4, were designed and synthesized as inhibitors for APH(3')s. These compounds are made of adenosine linked covalently to the 3'-hydroxyl of neamine (an aminoglycoside) via all-methylene tethers of 5 - 8 carbons. The K(i) values measured for these compounds indicated that affinities of APH(3')-Ia and APH(3')-IIa for compounds 2 and 8 (six- and seven-carbon tethers, respectively) were the best, and the inhibition constants for the two were comparable.