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J Comb Chem 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
JournalJ Comb Chem
Volume9
Issue2
Pages245-53
Date Published2007 Mar-Apr
ISSN1520-4766
KeywordsAurora Kinases, Cyclization, Protein-Serine-Threonine Kinases, Shikimic Acid, Substrate Specificity, Surface Plasmon Resonance
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

Alternate JournalJ Comb Chem
PubMed ID17348730
Grant ListGM38627 / GM / NIGMS NIH HHS / United States
N01-CO-12400 / CO / NCI NIH HHS / United States