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

J Comb Chem

Authors	Hua Miao John Tallarico Hiroyuki Hayakawa Karl Münger Jay Duffner Angela Koehler Stuart Schreiber Timothy Lewis
Keywords	Protein-Serine-Threonine Kinases Substrate Specificity Cyclization Surface Plasmon Resonance Aurora Kinases Shikimic Acid
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.
Year of Publication	2007
Journal	J Comb Chem
Volume	9
Issue	2
Pages	245-53
Date Published	2007 Mar-Apr
ISSN	1520-4766
URL
DOI	10.1021/cc060135m
PubMed ID	17348730
Links
Grant list	GM38627 / GM / NIGMS NIH HHS / United States N01-CO-12400 / CO / NCI NIH HHS / United States