Development of new stereodiverse diaminocyclitols as inhibitors of influenza virus neuraminidase.
A concise and modular approach to synthesize a new type of cyclopentene-based diaminocyclitol library from D-serine and L-serine has been developed, and key steps in this synthesis are an aza-Claisen rearrangement, a ring-closing metathesis, and a Baylis-Hillman reaction. The developed chemistry may offer a unique way to investigate the neuraminidase (NA) mutation by systematically mapping the changes within its binding sites.
Cui
Yi
Y
Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
Jiao
Zhaodong
Z
Gong
Jianxian
J
Yu
Quan
Q
Zheng
Xiaofeng
X
Quan
Junmin
J
Luo
Ming
M
Yang
Zhen
Z
D002384:Catalysis; D054812:Cyclitols / Q000494:pharmacology*; D053118:Influenza A Virus, H1N1 Subtype / Q000187:drug effects* / Q000201:enzymology*; D015394:Molecular Structure; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D009975:Orthomyxoviridae / Q000235:genetics*
D054812:Cyclitols; D009439:Neuraminidase