Peptide purification method using novel linker and solid-phase l

Details Peptide purification method using novel linker and solid-phase l Peptide purification method using novel linker and solid-phase l

1995-01-27

1997-07-15

Lukton, David

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Separation or purification

530334, 530337, 530345, 530336, A61K 3804

Patent

active

056484623

ABSTRACT:
Disclosed is a method of purifying a mature peptide with a free N-terminus group from a mixture of peptides comprising the mature peptide and immature end-capped peptides. The peptides are bound to a solid-phase support and are produced by solid phase synthesis. The mixture is contacted with a linker comprising a functional group at each terminus. The functional group at one terminus has the structure --SO.sub.2 --CH.sub.2 --CH.sub.2 --X, wherein X is an activated carbonate group which reacts selectively with N-terminus of the mature peptide to form a urethane linkage. The functional group at the other terminus is a thiol protected with an acid labile group. After cleaving the peptides from the solid support and thiol protecting group with acid, the mature peptide is separated from the mixture by forming a covalent bond between the liberated thiol and a solid support. Treatment with base cleaves the mature peptide from the linker to give a purified mature peptide.

REFERENCES:
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Funakoshi Proc Nat'l Acad Sci 88 6981 1991.
Krieger Proc Natl Acad Sci 73 3160 1976.
Krieger, D.E., et al., "Affinity Purification of Synthetic Peptides," Proc. Natl. Acad. Sci. USA, 73:3160-3164 (1976).
Fujii, N., et al., "Studies on Peptides. CLV. Evaluation of Trimethylsilyl Bromide as a Hard-Acid Deprotecting Reagent in Peptide Synthesis," Chem. Pharm. Bull., 35:3880-3883 (1987).
Funakoshi, S., et al., "Chemoselective One-Step Purification Method for Peptides Synthesized by the Solid-Phase Technique," Proc. Natl. Acad. Sci., 88:6981-6985 (1991).
Sucholeiki, I., and Lansbury, P.T., Jr., "Affinity Chromatographic Method for the Purification of Water-Insoluble Peptides," J. Org. Chem., 5478-5484.

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