Development of aspartic acid ligation for peptide cyclization derived from serine/threonine ligation  

作　　者：Ci Xu Jianchao Xu Han Liu Xuechen Li 

机构地区：[1]Department of Chemistry,State Key Laboratory of Synthetic Chemistry,The University of Hong Kong

出　　处：《Chinese Chemical Letters》2018年第7期1119-1122,共4页中国化学快报（英文版）

基　　金：supported by the Research Grants Council (Nos. 17309616, C6009-15G) of Hong Kong;The National Science Foundation of China (Nos. 21672180, 91753101);the Area of Excellence Scheme of the University of Grants Committee of Hong Kong (No. AoE/P-705/16)

摘　　要：Based on a mechanism analogous to the serine/threonine ligation, the aspartic acid ligation, which is facilitated by the γ-amino alcohol based ligation and oxidation, is developed and applied to the synthesis of cyclic peptides. The γ-hydroxyl group triggers the ring-chain tautomerization via a 6-endo-trig process,while the δ-hydroxyl group facilitates the oxidative cleavage of the vicinal diol to give carboxylic acid.Based on a mechanism analogous to the serine/threonine ligation, the aspartic acid ligation, which is facilitated by the γ-amino alcohol based ligation and oxidation, is developed and applied to the synthesis of cyclic peptides. The γ-hydroxyl group triggers the ring-chain tautomerization via a 6-endo-trig process,while the δ-hydroxyl group facilitates the oxidative cleavage of the vicinal diol to give carboxylic acid.

关 键 词：Aspartic acid ligation Peptide cyclization Serine/threonine ligation Ring-chain tautomerization Acyl transfer Selective oxidation 

分 类 号：O621.3[理学—有机化学]