A novel peptide synthesis using fluorous chemistry

Abstract

Three new fluorous supports for peptide synthesis, i.e., the trialkoxybenzhydryl-type (6), the Wang-type (7) and the tert-butyl-type support (8), were prepared. A bioactive peptide TRH was easily synthesized by an Fmoc strategy using the benzhydryl-type fluorous support with fluorous chemistry.

6.11 N-Acylation Reactions of Amines

“…For example, fluorous-based techniques to facilitate peptide purification are available 200 that employ N-fluoroprotected amino acid derivatives 201,202 as building blocks for synthesis, or use fluorous polymers as soluble supports for peptide synthesis. 202,203 Peptide synthesis has also been carried out using coupling reagents in ionic liquids, 204 or via peptide attachment to soluble ionic liquid supports that facilitate peptide purification. Small-to-medium-sized peptide sequences (up to 20-30 amino acids) have been routinely prepared using solution-phase techniques, 187 enabling peptide intermediates to be isolated, purified, deprotected, and coupled together to afford larger peptides (up to 60 amino acids) as required.…”

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

“…These heavy fluorous tags have been used in solution-phase peptide synthesis (Scheme 6). 18,19 In the synthesis of tripeptide pGlu-His-Pro-NH 2 , an excess amount of amino acid derivative was used in each coupling step. The unreacted reagent and coupling agents were removed by extraction with MeCN from the perfluorohexane (FC-72) layer.…”

Application of Fluorous Chemistry for Oligosaccharide Synthesis

“…Since then various oligosaccharide syntheses with the fluorous method have been described (8)(9)(10)(11)(12). We have also reported peptide and oligosaccharide synthesis by using various fluorous tags, the molecules of which contain polyamide bonds (Scheme 2) (13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26). In this review, we introduce recent progress made in oligosaccharide synthesis using the fluorous tag method.…”