Method for forming an amino acid thiohydantoin using an N-substi

Details Method for forming an amino acid thiohydantoin using an N-substi Method for forming an amino acid thiohydantoin using an N-substi

1990-06-29

1991-09-24

Hill, Jr., Robert J.

Chemistry: analytical and immunological testing

Peptide, protein or amino acid

Amino acid or sequencing procedure

436175, 436178, 530345, 530408, 530409, 530810, G01N 3368

Patent

active

050513680

ABSTRACT:
A method of forming an amino acid thiohydantoin from an N-protected amino acid or the C-terminal amino acid of an N-protected peptide. The amino acid is activated by reaction with a ketenimine, and the activated ester is converted to the thiohydantoin by reaction with silyl or pyridine isothiocyanate. The ketenimine is generated by treating an N-substituted isoxazolium compound, such as Woodwards Reagent K with a base, preferably in the presence of the amino acid. Also disclosed is a solid phase support having a derivatized N-substituted isoxazolium or ketenimine group for use in the method.

REFERENCES:
patent: 4935494 (1990-06-01), Miller
Tarr, G. E., Methods in Protein Sequence Analysis (1988), Section 4.1: "The Long Search for a Viable Method of C-Terminal Sequencing", pp. 129-151, B. Wittman-Leibold, Ed. Proceedings of the 7th International Conf., Berlin.
Hawke, D. H., et al., Microsequence Analysis of Peptides and Proteins: Trimethylsilylisothiocyanate as a Reagent for COOH-Terminal Sequence Analysis (1987) Analytical Biochem. 166, pp. 298-307.
Yamashita, S., Sequential Degradation of Polypeptides from the Carboxy-End Peptide Bonds (1971), Biochem. Biophys. Acta, 229 pp. 301-309.
Bailey, J. M., et al., Carboxy-terminal Sequencing: Formation and Hydrolysis of C-terminal Peptidylthiohydantoins (1990), Biochemistry vol. 29, No. 12, pp. 3145-3156.
Miller, C. G., et al., "Studies on the Use of Silyl Compounds for Protein Carboxy-Terminal Sequence Analysis", (1989), Techniques in Protein Chemistry, pp. 67-78, T. E. Hugh, Ed., Academic Press.
Kenner, G. W., et al., in Peptides IV, 136 "Selective Removal of the C-terminal Residue as a Thiohydantoin", (1953) J. Chem. Soc.

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