Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Synthesis of peptides
Reexamination Certificate
2004-06-18
2008-08-19
Gupta, Anish (Department: 1654)
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
Synthesis of peptides
C530S334000, C530S335000, C530S337000, C530S344000
Reexamination Certificate
active
07414106
ABSTRACT:
Disclosed herein is a new method for the solid phase peptide synthesis (SPPS) of C-terminal peptide α thioesters using Fmoc/t-Bu chemistry. This method is based on the use of an aryl hydrazine linker, which is totally stable to conditions required for Fmoc-SPPS. When the peptide synthesis has been completed, activation of the linker is achieved by mild oxidation. The oxidation step converts the acyl-hydrazine group into a highly reactive acyl-diazene intermediate which reacts with an α-amino acid alkylthioester (H-AA-SR) to yield the corresponding peptide α-thioester in good yield. A variety of peptide thioesters, cyclic peptides and a fully functional Src homology 3 (SH3) protein domain have been successfully prepared.
REFERENCES:
Ludolph B, Eisele F, Waldmann, H, SOlid-Phase Synthesis of Lipidated Peptide, Journal of American Chemical Society Communications, 2002, 124: 5954-5955.
Carmarero JA, Muir TW, Biosynthesis of a Head-to-Tail Cyclized Protin with Improved Biological Activity, Journal of American Chemical Society Communications, 1999, 121: 5597-5598.
Murray Goodmand, Kenneth C. Stueben, Peptide Syntheses Via Amino Acid Active Esters,J.Am. Chem. Soc. 1959, 81, 3980.
Camarero Julio A.
De Yoreo James J.
Mitchell Alexander R.
Gupta Anish
Ha Julie
Lawrence Livermore National Security LLC
Lee Ann M.
Lee John H.
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