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The Development of a Versatile Trifunctional Scaffold for Biological Applications
Author(s) -
Vaněk Václav,
Pícha Jan,
Fabre Benjamin,
Buděšínský Miloš,
Lepšík Martin,
Jiráček Jiří
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500255
Subject(s) - chemistry , scaffold , solid phase synthesis , derivatization , alkyne , combinatorial chemistry , alkyl , amphiphile , organic chemistry , polymer chemistry , copolymer , polymer , high performance liquid chromatography , biomedical engineering , peptide , medicine , biochemistry , catalysis
We describe the synthesis of a trifunctional scaffold constructed from a planar core of trimesic acid derivatized with three propargylamine moieties. The scaffold was attached to a solid‐phase resin through the carboxylic group of a fluorinated alkyl spacer arm. The orthogonal protection of two of the alkyne groups with triethylsilyl and triisopropylsilyl moieties enabled modular and efficient derivatization of the scaffold with three different azides by using solid‐phase synthesis on amphiphilic ChemMatrix resin. We showed that a fluorine label can be used to quantify the content of fluorine‐containing compounds by 19 F NMR spectroscopic analysis after cleavage from the resin. We have thus designed a versatile and convenient tool that could be useful for simple and rapid solid‐phase syntheses of combinatorial libraries of the scaffold‐based compounds, for example as new protein binders.