A novel, base-labile fluorous amine protecting group: synthesis and use as a tag in the purification of synthetic peptides

Fluorous Linker Units

“…Since F-Cbz was found partially deprotected during the acidic resin cleavage, Overkleeft and coworkers later on developed fluorous methylsufonylethoxycarbonyl (F-Msc) as a base-labile linker for amine group protection. [11] The Fustero group developed an easily cleavable F-TMSE linker and applied it in the synthesis of tripeptide 69 (Scheme 21.19). [38] The linker attachment of 65 was carried out under a standard esterification condition with diisopropylcarbodiimide (DIC) and N-hydroxybenzotriazole (HOBt).…”

“…Reaction conditions for attachment and cleavage of fluorous linkers are similar to those used for corresponding normal protecting groups. [9] [10] [11] [12] [13] [21] [18,19] [22] [23] [ [24][25][26] [ [27][28][29] [20] PMB (continued overleaf) Fluorous Linker Units 555 [14,15] [ 16,17] [30] [31,32] [33] …”

A Fluorous Capping Strategy for Fmoc‐Based Automated and Manual Solid‐Phase Peptide Synthesis

“…The more promising of these approaches have been the introduction of handles that provide an avenue for the facile removal of unwanted products, mainly those due to failed couplings. [4][5][6] We and others have demonstrated the use of fluorous capping during solid-phase synthesis of peptides, [7][8][9] oligonucleotides, [10] and carbohydrates. [11][12][13][14][15] In addition, fluorous compounds and solvents have found use in protein design, [16][17][18][19][20][21][22][23][24][25][26][27] reaction acceleration, [28] catalysis, [29][30][31][32][33][34] combinatorial chemistry, [35] proteomics [36] and organic separation methodology.…”

Amphiphilic perfluoroalkylated sulfones and sulfonate betaines

“…Perfluoroalkylated sulfones were applied in the synthesis of [2-(perfluorooctyl)ethyl]sulfonylethoxycarbonyl protecting group [12], as precursors of fluoroalkylated surfactants [13] and foaming agents [14]. Acrylates bearing fluoroalkyl and sulfone groups were reported for textile and oil repellents [15] in polymeric form or as hydrophilic medicinal prosthetic materials [16].…”