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Synthetic Routes to 3,4,5‐Trihydroxypiperidines via Stereoselective and Biocatalysed Protocols, and Strategies to N ‐ and O ‐Derivatisation
Author(s) -
Prichard Kate L.,
O'Brien Nicholas,
Ghorbani Mahdi,
Wood Adam,
Barnes Evan,
Kato Atsushi,
Houston Todd A.,
Simone Michela I.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801011
Subject(s) - stereoselectivity , chemistry , glycoside hydrolase , combinatorial chemistry , enzyme , stereochemistry , computational biology , biochemistry , biology , catalysis
Stereoselective and biocatalysed synthetic routes to 3,4,5‐trihydroxypiperidines and their N ‐ and O ‐derivatisations are reviewed. These iminosugars effectively modulate glycosidase enzymes and display biological activities in immunosuppression, as anti‐inflammatory agents and as anti‐viral agents. Syntheses to these building blocks and their N ‐ and O ‐derivatives are predicted to produce drug leads of high Fsp 3 index. This is also crucial in the collection of structure‐activity relationship data, particularly for diseases dependant on glycosidase modulation.