Group-selective fluorescence labeling

Combination of Group-Selective Fluorescence Labeling with GPC... 

A. Bohm, A. Potthast, S. Schiehser, T. Rosenau, H. Sixta, and P. Kosma, The FDAM method Determination of carboxyl profiles in cellulosic materials by combining groups selective fluorescence labeling with GPC, Biomacromolecules, 1 (2006) 1743-1750. 

We screened peptides that recognize and bind to a partial structure of DCMU from a combinatorial library of tetrapeptides on solid-phase. We used the 3,4-dichloroaniline (DCA) group as bait after taking into consideration the chemical structure of DCMU and its simple synthesis. To screen peptides that bind to the DCA group, a fluorescent-labeled dichloroaniline molecule (NBD-DCA) was synthesized by conjugating a dye with the dichloroaniline through a linker (Fig. 8.4). We selected a NBD moiety for the dye because of its small chemical structure and large Stokes shift. 

In Scheme 26 a selection of lipidated peptide sequences synthesized via this approach is shown. A variety of N- and H-Ras-derived peptide sequences was obtained bearing different types of lipids like farnesyl, palmitoyl, and geranylgeranyl and a fluorescent-labeled geranyl group. Furthermore, fluorescent markers like nitroben-zoxadiazole and photoactivatable groups were introduced. 

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