Carbocations in action. Design, synthesis, and evaluation of a highly acid-sensitive naphthalene-based backbone amide linker for solid-phase synthesis
Carbocations in action. Design, synthesis, and evaluation of a highly acid-sensitive naphthalene-based backbone amide linker for solid-phase synthesis
复制标题
DOI：
10.1021/ol062410j
复制
发表时间：
2006-12-07
期刊：
影响因子：
5.2
通讯作者：
Christensen, Jorn B.
中科院分区：
文献类型：
--
作者：
Pittelkow, Michael;Boas, Ulrik;Christensen, Jorn B.
本文介绍了一种基于区域特异性取代的四烷氧基萘醛核心的极酸不稳定主酰胺连接剂的设计、合成和性能。这个手柄可以在CH2Cl2中使用0.5%的TFA从固体载体上切割肽主酰胺（仲酰胺）。这个过程没有裂解叔丁基醚和叔丁基酯。该设计基于预测最稳定的烷氧基取代甲基萘基碳正离子的DFT研究。
[GRAPHICS]The design, synthesis, and properties of an extremely acid-labile backbone amide linker based on a regiospecifically substituted tetraalkoxy naphthaldehyde core are presented. This handle enables cleavage of peptide backbone amides (secondary amides) off a solid support using as little as 0.5% TFA in CH2Cl2. This proceeds without cleavage of tert-butyl ethers and tert-butyl esters. The design is based on a DFT study that predicted the most stabile alkoxy-substituted methyl naphthyl carbocation.