An activated building block for the introduction of the histidine side chain in aliphatic oligourea foldamers

作者：Nelli Yella Reddy; Douat Casassus Celine; Claudon Paul; Kauffmann Brice; Didierjean Claude; Guichard Gilles^*

来源：Tetrahedron, 2012, 68(23): 4492-4500.

DOI：10.1016/j.tet.2011.11.066

• Histidine
• Succinimidyl carbamate
• Oligourea
• Foldamer
• Solid phase synthesis
• Imidazole

A new N-Boc-protected monomer for the synthesis of oligourea foldamers containing the (1H-imidazolyl-4yl)methyl side chain of histidine, has been prepared in seven steps from Trt-His(tau-Trt)OMe. This protecting group combination on histidine was found to be critical to ensure efficient access to the requisite activated building block. This new derivative, suitable for solid phase synthesis, expands the current arsenal of building blocks with proteinogenic side chains useful for the design of peptidomimetic oligourea foldamers.

• 出版日期2012-6-10