Journal
ORGANIC LETTERS
Volume 18, Issue 11, Pages 2696-2699Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01160
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Funding
- GAP grant from ETPL of A*star [ETPL-QP-19-06]
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Palladium-catalyzed acetoxylation of the primary gamma-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 gamma-acetoxylated alpha-amino acid derivatives could be easily converted to gamma-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.
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