Synthesis of a library of stereo- and regiochemically diverse aminoglycoside derivatives.
A library of forty modified aminoglycosides was prepared in which the configuration and regiochemistry of two or three rings was widely varied. The library was based around three core ring systems: the 2-deoxystreptamine ring system found in the natural products, and both enantiomers of (1R*,2R*,4R*,5R*)-2,5-diamino-cyclohexane-1,4-diol and (1R*,3R*,4R*,6R*)-4,6-diaminocyclohexane-1,3-diol. In each case, the core was modified by glycosylation with one or two sugar rings. The absolute configuration of the sugar substituents (d or l), the configuration of the anomeric centres (alpha or beta), and the regiochemical arrangement of the amine(s) were varied.
Clique
Blandine
B
School of Chemistry, University of Leeds, Leeds, UK LS2 9JT.
Ironmonger
Alan
A
Whittaker
Benjamin
B
Colley
Jacqueline
J
Titchmarsh
James
J
Stockley
Peter
P
Nelson
Adam
A
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D013237:Stereoisomerism
D000617:Aminoglycosides