Composition and method for the release of protected peptidesfrom a resin

Abstract

The present invention provides a composition and a method for cleaving a peptide from a solid support resin. Hydrochloric acid in an organic water miscible solvent is used to cleave the peptide-resin attachment. Optionally, trifluoroethanol or hexafluoroisopropanol may be added to the cleavage composition to improve results. When using the present cleavage composition, an evaporation or other step to remove carboxylic byproducts is not necessary following the cleavage reaction. After the resin is filtered out of the cleavage mixture, the peptide may be immediately precipitated with water.

Description

Background of the invention [0001] The present invention relates to peptide synthesis and, in particular, to solid phase peptide synthesis, or to a combination of solid phase and solution phase peptide synthesis. Many methods of peptide synthesis are described in the literature (see, e.g., U.S. Pat. No. 6,015,881; Mergler et al. (1988) Tetrahedron Letters 29:4005-4008; Mergler et al. (1988) Tetrahedron Letters 29:4009-4012; Kamber et al. (eds), Peptides, Chemistry and Biology, ESCOM, Leiden (1992) 525-526; Riniker et al. (1993) Tetrahedron Letters 49:11065-11133; and Andersson et al. (2000) Biopolymers 55:227-250). [0002] In solid phase peptide synthesis (SPPS), amino acids or peptide groups are bound to a solid support resin. Amino acids are sequentially linked to the carrier-bound peptide until the desired peptide is formed. When the desired peptide is formed, it is cleaved from the resin. This requires cleavage of the attachment between the peptide and the resin and su...

AI Technical Summary

Problems solved by technology

This extra step and the solvent required creates additional time, expense, and creates waste that needs to be disposed of, which in turn creates additional costs