Chemical peptide ligation with three or more components

Details Chemical peptide ligation with three or more components Chemical peptide ligation with three or more components

2011-02-08

2011-02-08

Tsang, Cecilia (Department: 1654)

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

25 or more amino acid residues in defined sequence

Reexamination Certificate

active

07884182

ABSTRACT:
The invention provides a method of assembling oligopeptide intermediates in a native chemical ligation reaction that eliminates self-ligation of bi-functional intermediates. An important aspect of the invention is a bi-functional intermediate with an N-terminal heterocyclic protecting group which effectively prevents self-ligation in the chemical assembly process. The present invention is useful in methods for convergent synthesis of polypeptides and proteins and improves the efficiency of native chemical ligation reactions, particularly where three or more peptide fragments are used to assemble a polypeptide or protein product.

REFERENCES:
patent: 5801148 (1998-09-01), Gyorkos et al.
patent: 2005/0113563 (2005-05-01), Botti et al.
patent: WO 00/18789 (2000-04-01), None
Villain et al Chemical Ligation of Multiple Peptide Fragments Using a New Protection Strategy, Peptides: Wave of the Future (2001), p. 107.
Botti, P. et al., “Native chemical ligation using removable N1pha-(1-phenyl-2-mercaptoethyl) auxiliaries,” Tetrahedron Letters, vol. 42, No. 10; pp. 1831-1833 (Mar. 4, 2001).
Canne, L.E. et al., “Extending the applicability of native chemical ligation,” J. Am. Chem. Soc., vol. 118, No. 25; pp. 5891-5896 (Jun. 26, 1996).
Freidinger, R. M., “Computer graphics and chemical synthesis in the study of conformation of biologically active peptides,” Pept.: Synth., Struct, Funct., Proc. Am. Pept. Symp., 7th (1981) pp. 673-683 (eds.: Rich, D.H. and E. Gross).
Villain, M. et al., “Chemical ligation of multiple peptide fragments using a new protection strategy,” in: Peptides: The Wave of the Future, Proceedings of the 2nd Int'l and 17th American Peptide Symposium, San Diego, CA, USA (Jun. 9-14, 2001) pp. 107-108 (eds. Lebl, M. and R.A. Houghten).

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