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Ring-opening and ring-closing reactions of a shikimic acid-derived substrate leading to diverse small molecules.

Publication TypeJournal Article
AuthorsMiao, H., Tallarico JA, Hayakawa H., Münger K., Duffner JL, Koehler AN, Schreiber SL, and Lewis TA
AbstractAn epoxide derived from (-)-shikimic acid was attached to a solid support and used to synthesize over 5000 diverse small molecules. Key transformations include a Lewis acid-catalyzed epoxide opening with amines and an intramolecular Heck reaction with aryl iodides. Compounds derived from this pathway were printed onto small-molecule microarrays and screened for binding to proteins. Compounds that bound to Aurora A kinase were characterized using surface plasmon resonance.
Year of Publication2007
JournalJournal of combinatorial chemistry
Volume9
Issue2
Pages245-53
Date Published (YYYY/MM/DD)1969/12/31
ISSN Number1520-4766
DOI10.1021/cc060135m
PubMedhttp://www.ncbi.nlm.nih.gov/pubmed/17348730?dopt=Abstract