Fluorous Chemistry for Synthesis and Purification of Biomolecules: Peptides, Oligosaccharides, Glycopeptides, and Oligonucleotides

Abstract

Fluorous chemistry has advanced well beyond the scope of biphasic catalysis and high-throughput synthesis of small molecules. This review describes the recent development of fluorous technologies in the synthesis and purification of biomolecules including peptides, oligosaccharides, glycopeptides, and oligonucleotides.Highly fluorinated (fluorous) molecules are lipophobic and hydrophobic, 1 but they have strong interaction with fluorous separation media. This unique property has been exploited for phase separation of fluorous-tagged molecules from non-fluorous molecules by liquid-liquid extraction (LLE) with fluorous solvents or by solid-phase extraction (SPE) and chromatography with fluorous silica gel. 2 In 1994 Horváth and Rábai introduced the concept of "fluorous biphasic catalysis" for catalyst recovery. 3,4 Since then, Curran group at the University of Pittsburgh, Fluorous Technologies, Inc., and others have developed a large collection of fluorous catalysts, reagents, scavengers, protecting groups for "fluorous synthesis" of small molecules. 5 ' 8 Now fluorous technologies have been applied to synthesis arid separation of biomolecules.

Fluorous-Enhanced Multicomponent Reactions for Making Drug-Like Library Scaffolds

“…F-MCR protocols for synthesis of drug-like molecules described in this paper examplify the integration of MCR, microwave reaction, and F-SPE technique to improve the efficiency of existing chemistry and to explore new chemistry as well. The broad fluorous technology platform generates more and more impacts on synthesis, purification, immoblization, microarray, and screening of small melocules and biomolecules for life scince applications [28,55]. One-pot synthesis of a novel hexacyclic ring system 29 and proposed mechanism…”