Palladium-catalyzed acetoxylation of the primary γ-C(sp(3))-H bonds in the amino acids Val, Thr, and Ile was achieved using a newly discovered 5-methylisoxazole-3-carboxamide directing group. The γ-acetoxylated α-amino acid derivatives could be easily converted to γ-mercapto amino acids, which are useful for native chemical ligation (NCL). The first application of NCL at isoleucine in the semisynthesis of a Xenopus histone H3 protein was also demonstrated.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.6b01160DOI Listing

Publication Analysis

Top Keywords

amino acids
12
γ-mercapto amino
8
acids native
8
native chemical
8
chemical ligation
8
5-methylisoxazole-3-carboxamide-directed palladium-catalyzed
4
palladium-catalyzed γ-csp3-h
4
γ-csp3-h acetoxylation
4
acetoxylation application
4
application synthesis
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!