Native chemical ligation with three or more components

Details Native chemical ligation with three or more components Native chemical ligation with three or more components

2002-05-31

2010-02-16

Tsang, Cecilia (Department: 1654)

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Synthesis of peptides

Reexamination Certificate

active

07662914

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 cyclic thiazolidine 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: 6372912 (2002-04-01), Doring et al.
patent: 19919336 (2000-11-01), None
patent: 2000-309572 (2000-11-01), None
Villain et al Chemical Ligation of Multiple Peptide Fragments Using a New Protection Strategy, Peptides: Wave of the Future (2001), p. 107.
Tam JP. “Tandem ligation of unprotected peptides through thiaprolyl and cysteinyl bonds in water,” J Am Chem Soc. Mar. 21, 2001;123(11):2487-94.
Mitchell, et al., Int J Peptide Protein Res, 36(4): 350-355 (1990).

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