119-04-0Relevant articles and documents
Characterization of a radical S-adenosyl-l-methionine epimerase, NeoN, in the last step of neomycin B biosynthesis
Kudo, Fumitaka,Hoshi, Shota,Kawashima, Taiki,Kamachi, Toshiaki,Eguchi, Tadashi
, p. 13909 - 13915 (2014)
The last step of neomycin biosynthesis is the epimerization at C-5 of neomycin C to give neomycin B. A candidate enzyme responsible for the epimerization was a putative radical S-adenosyl-l-methionine (SAM) enzyme, NeoN, which is uniquely encoded in the n
Synthesis of ring II/III fragment of Kanamycin: A new minimum structural motif for aminoglycoside recognition
Zárate, Sandra G.,Bastida, Agatha,Santana, Andrés G.,Revuelta, Julia
, (2019/08/20)
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.
TOTAL SYNTHESIS OF NEOMYCIN B
Usui, Takayuki,Umezawa, Sumio
, p. 133 - 144 (2007/10/02)
Total synthesis of neomycin B, a pseudo-tetrasaccharide aminoglycoside antibiotic, has been achieved through two key glycosylation reactions.Coupling of 3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-L-idopyranosyl chloride with 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose under modified Koenigs-Knorr conditions gave 70percent of the desired β-L disaccharide (3) and corresponding to neobiosamine in structure.After deisopropylidenation of 3 and acetylation, 1,2-di-O-acetyl-3-O-(3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-β-L-idopyranosyl)-5-O-benzoyl-D-ribofuranose was coupled to HO-5 of 3,2',6'-tri-N-(benzyloxycarbonyl)-1-N:6-O-carbonyl-3',4'-di-O-(o-methoxybenzoyl)neamine, using trimethylsilyl trifluoromethanesulfonate, to give 60percent of the pseudo-tetrasaccharide 19 possessing the framework and masked functionality corresponding to neomycin B.Deblocking and reduction of the azido groups then gave neomycin B.