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Versatile approach to encoding combinatorial organic syntheses using chemically robust secondary amine tags.

Z J Ni·D Maclean·C P Holmes·M M Murphy·B Ruhland·J W Jacobs·E M Gordon·M A Gallop
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Abstract

Encoded combinatorial organic synthesis has recently emerged as a powerful tool for the discovery of biologically active compounds from complex chemical libraries. This report describes a new encoding methodology that uses chemically robust secondary amines as tags. These amines are incorporated into an N-[(dialkylcarbamoyl)methyl]glycine-coding oligomer through simple chemistry that is compatible with a wide range of polymer-supported transformations useful in combinatorial synthesis. In the decoding process acidic hydrolysis of the tagging polymer regenerates the secondary amines, which after dansylation are resolved and detected at sub-picomole levels by reversed-phase HPLC. The versatility of this strategy is demonstrated here by encoded syntheses of members of several representative heterocyclic compound classes, including beta-lactams, 4-thiazolidinones, and pyrrolidines.

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Anti-Bacterial AgentsLactamsPyrrolidinesThiazolesJournal Article

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Z J Ni, D Maclean, C P Holmes, M M Murphy, B Ruhland, J W Jacobs, E M Gordon, M A Gallop. 1996-04-12. Versatile approach to encoding combinatorial organic syntheses using chemically robust secondary amine tags.. https://doi.org/10.1021/jm960043j

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