Composition and method for the release of protected peptidesfrom a resin

A composition and resin technology, applied in the field of peptide synthesis, to achieve the effect of increasing yield and purity, and reducing processing time

Inactive Publication Date: 2009-05-20
MALLINCKRODT INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This extra step and the solvent required creates additional time, expense, and c

Method used

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Examples

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Embodiment

[0016] The following examples briefly describe the synthesis of peptides utilizing the present invention. Although the examples describe the synthesis of enfuvirtide, the principles described can be applied to any peptide, preferably any protected peptide, synthesized on an acid labile support such as chlorotrityl Chloride (CTC) resin, Sieber resin or Rink resin. Non-limiting examples of such peptides include pramlintide, exenatide, enfuvirtide, calcitonin, and PYY-3-36. The following examples are only preferred methods for preparing enfuvirtide, and are not meant to limit it in any way.

[0017] Loading of FMOC-amino acids on CTC resin:

[0018] 1. General method

[0019]A solution of FMOC amino acids (0.8 to 1.5 mole eq.) containing DIEA (1 to 1.7 mole eq.) in DCM or DMF+DCM (4:1) was added to pre-swelled CTC resin (1 mole eq.) , and shaken for 2 hours under nitrogen flow. It was drained and shaken with a MeOH+DIEA (9:1) mixture for 20-30 minutes to destroy excess activ...

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PUM

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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...

Claims

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Application Information

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IPC IPC(8): C07K1/12C07C31/38C07C31/40
Inventor 克里帕·S·斯里瓦斯塔瓦
Owner MALLINCKRODT INC
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