title: Biomolecular assemblies combining two orthogonal copper-mediated ligations in a one-pot reaction.
abstract: The access to multifunctional biomolecular compounds involves multistep reactions usually with a complicated protection scheme and lengthy separation processes. The development of a strategy combining several orthogonal ligations is highly desirable. Herein, we introduce a new method that involves two orthogonal copper-mediated ligations of azide with alkyne, and amine with thioacid. We established compatible conditions to carry out molecular assemblies of three different chemical components in a single one-pot reaction. The effectiveness of the method was demonstrated in the synthesis of biomolecular compounds that are known to target tumor tissue. The simple reaction conditions suggest that this strategy of combining several orthogonal ligations could have wide potential for the chemical synthesis of complex macromolecules.
authors: Univ. Grenoble Alpes, DCM UMR 5250, 38000 Grenoble (France), CNRS, DCM UMR 5250, 38000 Grenoble (France), Fax: (+33) 4-56-52-08-03.
authors: Adrien
authors: A
authors: Grassin
authors: Michaël
authors: M
authors: Claron
authors: Didier
authors: D
authors: Boturyn
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry; D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000480:Alkynes; D000588:Amines; D001386:Azides; D013438:Sulfhydryl Compounds; D003300:Copper
keywords: CuAAC; amidation; click chemistry; copper; one-pot reaction