205192-05-8Relevant academic research and scientific papers
Synthesis of l -Pyranosides by Hydroboration of Hex-5-enopyranosides Revisited
?opatkiewicz, Grzegorz,Mlynarski, Jacek
, p. 7545 - 7556 (2016)
Extensive study of the diastereoselective synthesis of l-pyranosides utilizing hydroboration of substituted exo-glucals (5-enopyranosides) obtained from d-sugars is presented. On the basis of this study we present the empirical rules describing the reacti
Divergent synthesis of L-sugars and L-iminosugars from D-sugars
Takahashi, Hideyo,Shida, Tomomi,Hitomi, Yuko,Iwai, Yoshinori,Miyama, Namisa,Nishiyama, Kazusa,Sawada, Daisuke,Ikegami, Shiro
, p. 5868 - 5877 (2008/03/11)
An efficient divergent synthesis of L-sugars and L-iminosugars from D-sugars is described. The important intermediate. δ-hydroxyalkoxamate. prepared from D-glucono-/galactono-1,5-lactone, was cyclized under Mitsunobu conditions to give the O-cyclized oxim
Synthesis of gem-difluorocarba-d-glucose: A step further in sugar mimesis
Deleuze, Aurelie,Menozzi, Candice,Sollogoub, Matthieu,Sinay, Pierre
, p. 6680 - 6683 (2007/10/03)
A rearrangement strategy was used for the synthesis of α- and β-gem-difluorocarba-D-glucose, which are close congeners of α- and β-D-glucose, in which the endocyclic oxygen atom has been replaced by a gem-difluoromethylene group (see scheme). The two anom
Probing the specificity of aminoglycoside-ribosomal RNA interactions with designed synthetic analogs
Alper, Phil B.,Hendrix, Martin,Sears, Pamela,Wong, Chi-Huey
, p. 1965 - 1978 (2007/10/03)
The binding of neomycin B and related aminoglycoside antibiotics to the prokaryotic ribosomal RNA decoding region has been investigated using a recently developed surface plasmon resonance assay. A number of naturally occurring aminoglycosides containing a neamine or neamine-like substructure bind specifically to a model of the site of the ribosomal decoding region RNA. This recognition event is the basis of the antibacterial activity of this class of compounds. A series of analogs was designed and synthesized to probe the role of neomycin ring IV (2,6-dideoxy-2,6-diamino-β-L- idopyranose). The binding results indicate that the positive charge presented on the idose ring is necessary for specific binding in vitro and cannot be replaced by amines attached via flexible linkers. However, the antibiotic activity (minimum inhibitory concentration) of the analog where ring IV is replaced with a diamine tail is the same as neomycin B in a liquid culture assay against Escherichia coli.
