5-Methylisoxazole-3-carboxamide-Directed Palladium-Catalyzed γ-C(sp3)-H Acetoxylation and Application to the Synthesis of γ-Mercapto Amino Acids for Native Chemical Ligation

被引：30

作者：

Pasunooti, Kalyan Kumar ^{[1
]}

Yang, Renliang ^{[1
]}

Banerjee, Biplab ^{[1
]}

Yap, Terence ^{[1
]}

Liu, Chuan-Fa ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Biol Sci, Singapore 637551, Singapore

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 11期

关键词：

C-H FUNCTIONALIZATION; PEPTIDE LIGATION; DESULFURIZATION; ARYLATION; PROTEINS; BONDS; OXIDATION; EFFICIENT; PROBES;

D O I：

10.1021/acs.orglett.6b01160

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2696 / 2699

页数：4

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