Synthesis of Mixed 伪/尾2,2-Peptides by Site-Selective Ring-Opening of Cyclic Quaternary Sulfamidates
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- 作者：Nuria Mazo ; Iv谩n Garc铆a-Gonz谩lez ; Claudio D. Navo ; Francisco Corzana ; Gonzalo Jim茅nez-Os茅s ; Alberto Avenoza ; Jes煤s H. Busto ; Jes煤s M. Peregrina
- 刊名：Organic Letters
- 出版年：2015
- 出版时间：December 4, 2015
- 年：2015
- 卷：17
- 期：23
- 页码：5804-5807
- 全文大小：301K
- ISSN：1523-7052
文摘
A method for site- and stereoselective peptide modification using a cyclic sulfamidate scaffold containing peptides is described. A peptide synthesis strategy allowing the rapid generation of mixed 伪/尾-peptides incorporating a sulfamidate residue, derived from 2-methylisoserine, has been generalized. The unique electrophilic nature of this scaffold for nucleophilic substitution at a quaternary center with total inversion of its configuration, which was demonstrated computationally, allows for site-selective conjugation with various nucleophiles, such as anomeric thiocarbohydrates and pyridines. This strategy provides rapid access to complex thioglyco-伪/尾-conjugates and charged 伪/尾-peptides.