Benzotriazole-1-yl-N-oxy phosphonium coupling agent

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C548S112000, C530S333000

Reexamination Certificate

active

10551522

ABSTRACT:
Novel phosphonium salts of benzotraizoles, which are highly reactive coupling agents, and are particularly useful in peptide synthesis, are disclosed. Further disclosed is a process of preparing the novel phosphonium salts and methods utilizing same for preparing peptides.

REFERENCES:
Albericio et al. “On the Use of PyAOP, A Phosphonium Salt Derived From HOAt, in Solid-Phase Peptide Synthesis”, Tetrahedron Letters, 38(27): 4853-4856, 1997.
Carpino et al. “1-Hydroxy-7-Azabenzotriazole. An Efficent Peptide Coupling Additive”, Journal of the American Chemical Society, 115: 4397-4398, 1993.
“IUPAC-IUB Commission on Biochemical Nomenclature Symbols for Amino-Acid Derivatives and Peptides Recommendations (1971)”, The Journal of Biological Chemistry, 247(4):977-983, 1972.
Ueki et al. “A New One-Pot Method for Fmoc Solution Synthesis”, Peptides, Proceedings of the 25th European Peptide Symposium, Akademiai Kiado, Budapest, p. 252-253, 1998.
Coste et al. “PyBOP®: A New Peptide Coupling Reagent Devoid of Toxic By-Product”, Tetrahedron Letters, 31(2): 205-208, 1990.
Albericio et al. “Coupling Methods: Solid-Phase Formation of Amide and Ester Bonds”, Solid-Pase Synthesis: A Practical Guide, Chap.6: 275-330, 2000.
Vendrell et al. “N-[Chloro(Dimethylamino)Methylene]-N-Methylmethanaminium Chloride (TMUCI CI), the Reagent of Choice for the Solid-Phase Synthesis of Anilidis”, Tetrahedron Letters, 46(32): 5383-5386, 2005.
PCT Search Report and Written Opinion PCT/IL05/00886 dated Mar. 22, 2006.

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