Premium
Bifunctional Diaminoterephthalate Scaffolds as Fluorescence Turn‐On Probes for Thiols
Author(s) -
Freimuth Lena,
Christoffers Jens
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.201500494
Subject(s) - bifunctional , turn (biochemistry) , fluorescence , chemistry , biophysics , combinatorial chemistry , biochemistry , catalysis , biology , physics , quantum mechanics
The fluorescent diaminoterephthalate scaffold was equipped by amidation with three types of reactive functions: thiols for metal‐surface binding, alkynes for click reactions, and maleimides for ligation with proteins. Starting from a succinyl succinate derivative with two orthogonally cleavable ester functions, three monoamides (38–57 % yield over three steps) and two bisamides (19 and 25 % yield over five steps) were prepared. Although alkyne and thiol derivatized compounds showed reasonable luminescence behavior ( Φ ≈1–4 %), the fluorescence was quenched by the maleimide moiety. It was turned on (10‐ to 20‐fold increase of fluorescence quantum yield) by conjugate addition of thiols.