You are here

Journal of combinatorial chemistry DOI:10.1021/cc060135m

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

Publication TypeJournal Article
Year of Publication2007
AuthorsMiao, H, Tallarico, JA, Hayakawa, H, Münger, K, Duffner, JL, Koehler, AN, Schreiber, SL, Lewis, TA
JournalJournal of combinatorial chemistry
Volume9
Issue2
Pages245-53
Date Published1969/12/31
ISSN1520-4766
Abstract

An 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.

URLhttp://dx.doi.org/10.1021/cc060135m
DOI10.1021/cc060135m
Pubmed

http://www.ncbi.nlm.nih.gov/pubmed/17348730?dopt=Abstract