Synthesis of Aminoglycosides

S. Umezawa, Structure and synthesis of aminoglycoside antibiotics, Adv. Carbokydr. Chem. Biodtem 3(7.111 <1974). 

S. Umezawa Recent advances in the synthesis of aminoglycoside antibiotics... 

Park WKC, Auer M, Jaksche H, Wong CH, Rapid combinatorial synthesis of aminoglycoside antibiotic mimetics use of a polyethylene glycol-linked amine and a neamine-derived aldehyde in multiple component condensation as a strategy for the discovery of new inhibitors of the HIV RNA Rev responsive elements, J. Am. Chem. Soc., 118 10150-10155, 1996. 

Sumio Umezawa s achievements have been recognized by many awards, including the Gijuku Prize (Keio University) in 1949 for Chemical Studies onPenicillin and the Fukuzawa Prize (Keio University) in 1963 for Studies on Antimicrobial Substances and Related Compoimds. He also received the Chemical Society of Japan Award for Studies on Antimicrobial Substances and Related Compounds in 1964 and tire Japan Academy Prize for Studies on tire Synthesis of Aminoglycoside Antibiotics in 1980. Sumio was deeply moved when he received the Fujihara Prize in 1982 for Total Synthesis of Streptomycin, since this award... 

Recent Advances in the Synthesis of Aminoglycoside Antibiotics, S. Umezawa, Pure Appl. Chem., 50 (1978) 1453-1476. 

H Saito, H Yoshikawa, Y Nishimura, S Kondo, T Takeuchi, H Umezawa. Studies on lignan lactone antitumor agents.I. Synthesis of aminoglycosidic lignan variants related to podophyUotoxin. Chem Pharm Bull 34 3733-3740, 1986. 

Walker J B (2002). Enzymatic synthesis of aminoglycoside antibiotics novel adeno-sylmethionine 2-deoxystreptamine N-methyltransterase activities in hygromycin B-and spectinomycin-producing Streptomyces spp. and uses of the methylated products. Appl. Environ. Microbiol. 68 2404-2410. 

III. 1.1 Total Synthesis of Aminoglycosides with 2 Carbohydrate Units and... 

Total Synthesis of Aminoglycosides with 3 Carbohydrate Units. . 122... 

Total Synthesis of Aminoglycosides Composed of Three Carbohydrate... 

Synthesis of Aminoglycosides Active against Resistant Bacteria. 164... 

I. Charles, L. Xue, and D. P. Arya, Synthesis of aminoglycoside-DNA conjugates, Bioorg. Med. Chem. Lett., 12 (2002) 1259-1262 I. Charles and D. P. Arya, Synthesis of neo-mycin-DNA/peptide nucleic acid conjugates, J. Carbohyd. Chem., 24 (2005) 145-160. 

Recent advances in the synthesis of aminoglycoside antibiotics have been reviewed. Derivatized dihydrostreptomycin has been hydrolysed to give a chiral streptidine derivative (9), which could be condensed with a dihydrostrepto-biosaminyl chloride derivative to give a- and j3-glycosides, the a-form yielding dihydrostreptomycin again on deprotection. ... 

Reviews have appeared on the synthesis of aminoglycoside antibiotics, and on the formation of new aminocyclitol antibiotics by mutants of amino-cyclitol-producing organisms fed with aminocyclohexanol or related subunits. The structures of eight minor components of the nebramycin complex elaborated by Streptomyces tenebrarius have been elucidated besides neamine and related pseudo-disaccharides, the new components are pseudo-trisaccharides related to kanamycin B, and the 3 -hydroxy analogue of the principal component of the complex, apramycin (see Vol. 10, p. 130). ... 

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