An activated building block for the introduction of the histidine side chain in aliphatic oligourea foldamers |
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| Authors: | Yella-Reddy Nelli Céline Douat-Casassus Paul Claudon Brice Kauffmann Claude Didierjean Gilles Guichard |
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| Affiliation: | 1. Université de Bordeaux—CNRS UMR5248, Institut Européen de Chimie et Biologie, CBMN, 2 rue Robert Escarpit, Pessac 33607, France;2. CNRS, Institut de Biologie Moléculaire et Cellulaire, Laboratoire d’Immunologie et Chimie Thérapeutiques, Strasbourg 67000, France;3. Université de Bordeaux—CNRS UMS3033, Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, Pessac 33607, France;4. CRM2, UMR-CNRS 7036, Groupe Biocristallographie, Université Henri Poincaré, BP 239, Vandoeuvre 54506, France |
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| Abstract: | 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(τ-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. |
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