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Biomolecular Assemblies Combining Two Orthogonal Copper‐Mediated Ligations in a One‐Pot Reaction
Author(s) -
Grassin Adrien,
Claron Michaël,
Boturyn Didier
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500293
Subject(s) - combinatorial chemistry , alkyne , amine gas treating , copper , macromolecule , chemistry , nanotechnology , materials science , organic chemistry , catalysis , biochemistry
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.