294204-07-2Relevant academic research and scientific papers
All eight stereoisomeric D-glyconic-δ-lactams: Synthesis, conformational analysis, and evaluation as glycosidase inhibitors
Nishimura, Yoshio,Adachi, Hayamitsu,Satoh, Takahiko,Shitara, Eiki,Nakamura, Hikaru,Kojima, Fukiko,Takeuchi, Tomio
, p. 4871 - 4882 (2007/10/03)
An efficient and general synthetic route to all eight stereoisomeric D-glycono-δ-lactams has been developed. The strategy involves, as a key step, a stereodivergent δ-lactam formation with configurational retention or inversion at C-4 of a starting γ-lactone to lead to two epimers of δ-lactam from one parent γ-lactone. Conformations of eight glycono-δ-lactams were examined by X-ray crystallographic analysis and molecular modeling. Analyses of conformation and glycosidase-inhibition provide useful information for the design of new glycosidase inhibitors.
