Biotinylating reagent and purification process for synthesized p

Details Biotinylating reagent and purification process for synthesized p Biotinylating reagent and purification process for synthesized p

1993-03-26

1995-02-21

Hill, Jr., Robert J.

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Separation or purification

530345, 530333, 530334, 530337, A61K 3702

Patent

active

053917111

ABSTRACT:
This invention relates to a biotinylating reagent being used in purification process for synthesis mature peptide. The reagent has at one terminus a functional group capable of forming a bond with the N-terminus amino group of the mature peptide. The bond is stable to the final deprotection reaction under acidic condition at the post-synthesis step of the peptide synthesis process while the bond is specifically cleaved under a difined condition such as basic condition. The reagent also has at the other terminus a biotinyl group. The biotinyl-avidin coupling is used when the reagent modified mature peptide are immobilized selectively on avidin-agarose column. The compounds having following formula (II) are preferable as the reagent. ##STR1## wherein Y is one of ##STR2##

REFERENCES:
Funakoshi J. Chromatogr 638, 21 (1993).
D. R. Gretch, et al., "The Use of Biotinylated Monoclonal Antibodies and Streptavidin Affinity Chromatography to Isolate Herpesvirus Hydrophobic Proteins or Glycoproteins", Analytical Biochemistry, 163:270-277 (1987).
D. E. Krieger, et al., "Affinity Purification of Synthetic Peptides", Proc. Natl. Acad. Sci. USA, 73(9):3160-3164, (1976).
T. J. Lobl, et al., "On-Resin Biotinylation of Chemically Synthesized Proteins for One-Step Purification", Analytical Biochemistry, 170:501-511 (1988).
C. A. Mouton, et al., "A Reagent for Covalently Attaching Biotin to Proteins Via a Cleavable Connector Arm", Archives of Biochemistry and Biophysics, 218(1):101-108 (Oct. 1, 1982).
M. Shimkus, "A Chemically Cleavable Biotinylated Nucleotide: Usefulness in the Recovery of Protein-DNA Complexes from Avidin Affinity Columns", Proc. Natl. Acad. Sci. USA, 82:2593-2597 (May 1985).
N. M. Green "Avidin 3. The Nature of the Biotin-Binding Site", Biochem. J., 89:599 (1963).
N. M. Green and E. J. Toms "The Properties of Subunits of Avidin Coupled to Sepharose", Biochem. J., 133:698-700 (1973).
N. Fujii, et al., "Studies of Peptides CLV. Evaluation of Trimethylsilyl Bromide as a Hard-Acid Deprotecting Reagent in Peptide Synthesis", Chem. Pharm. Bull, 35(9):3880-3883 (1987).
S. Funakoshi, et al., "A Modified Benzhydrylamine as a Handle Reagent for the Solid Phase Synthesis of Peptide Amides Based on the Fluorenylmethoxycarbonyl Method" J. Chem. Soc. Chem. Commun., 383-384 (1988).
G. J. Tesser and I. C. Balvert-Geers, et al., "The Methylsulfonylethyloxycarbonyl Group, A New and Versatile Amino Protective Function", Int. J. Peptide Protein Res., 7:295-305 (1975).
J. Diaz, "A Large-Scale Synthesis of Somatostatin for Clinical Use by a Novel Alternating Solution/Solid-Phase Procedure", Bioorganic Chemistry 8:429-442 (1979).
Merck Index, 11th Edition, p. 4472 (1989).

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