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J Comb Chem. 2007 Mar-Apr;9(2):245-53.

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

Author information

1
Broad Institute of Harvard and MIT, 7 Cambridge Center, Cambridge, Massachusetts 02142, USA.

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.

PMID:
17348730
DOI:
10.1021/cc060135m
[Indexed for MEDLINE]

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