The Development of a Versatile Trifunctional Scaffold for Biological Applications. Issue 17 (30th April 2015)

• Record Type: Journal Article
• Authors: Vaněk, Václav; Pícha, Jan; Fabre, Benjamin; Buděšínský, Miloš; Lepšík, Martin; Jiráček, Jiří
• Is Part Of: European journal of organic chemistry. Issue 17(2015)
• Page Start: 3689
• Page End: 3701
• Publication Date: 2015-04-30
• Subjects: Solid‐phase synthesis -- Protein mimics -- Click chemistry -- Alkynes -- Copper -- Azides; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500255
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : The development of a trifunctional scaffold derivatized with three orthogonally protected alkyne moieties that is useful for the solid‐phase synthesis of combinatorial libraries is described.