AI Article Synopsis
- A novel zinc carbenoid-mediated chain-extension reaction has been successfully applied to create functionalized peptide isostere.
- The method was tested on a cleavage site of the human CVM protease, demonstrating its effectiveness in synthesizing an amino acid-derived alpha-unsubstituted gamma-keto ester that resembles a tetrapeptide.
- A strategic use of protecting groups and oxazolidinone auxiliaries allowed for effective diastereocontrol in a tandem chain-extension-aldol reaction, with stereoselectivity confirmed through an oxidative cleavage process.
Article Abstract
The application of a zinc carbenoid-mediated chain-extension reaction to a functionalized peptide isostere is reported. The cleavage site of human CVM protease was utilized as a target for testing the synthetic methodology. The utility of this chain-extension reaction is demonstrated in the preparation of an amino acid-derived alpha-unsubstituted gamma-keto ester, which is incorporated into a framework that mimics a tetrapeptide. The identification of a suitable protecting group strategy facilitated the application of a tandem reaction for the incorporation of an alpha-side chain, and the use of an oxazolidinone auxiliary provided excellent diastereocontrol in a tandem chain-extension-aldol reaction. Stereoselectivity of the tandem chain-extension-aldol reaction was determined through application of a CAN-mediated oxidative cleavage reaction.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2680025 | PMC |
| http://dx.doi.org/10.1021/jo801993k | DOI Listing |
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