Method of peptide synthesis

Details Method of peptide synthesis Method of peptide synthesis

1996-01-18

1998-12-15

Tsang, Cecilia J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Phosphorus containing

568 9, 423462, C07F 902, C01B 700

Patent

active

058499547

ABSTRACT:
The present invention relates to a process for forming an N-.alpha.-amino protected amino acid fluoride in situ by reacting an N-.alpha.-amino protected amino acid with an ionic fluoride salt in the presence of a peptide coupling agent. It is also directed to the use of the amino acid fluoride thus formed in peptide synthesis.

REFERENCES:
patent: 4069048 (1978-01-01), Tsubota et al.
Colton, et al. "Aluminum-27 N.M.R. Studies of Aluminum Fluoro Complexes in Dichloromethane Solution", Aust. J. Chem., 1989, 42, 1605-9.
Caplus Abstract No. 1980: 620812 to Uson et al, J. Organomet. Chem. (1980) 194(3) pp. 271-275.
Landini, et al., "Convenient Procedures for the Prepartion of Lipophilic Quaternary Onium Fluorides, Hydrogendifluorides and Dihydrogentrifluorides via Ion Exchange in Two-Phase Systems," Synthesis, 1988, pp. 953-954.
Abstract 1979:491910 Document No. 91: 91910 to Ogilvie et al., Nucleic Acids. Res. 6(6), 2261-73 (1979).
Abstract 1979: 137769 Document No. 90: 137769 to Oligive et al, Tetra. Lett vol. 35 3203-6 (1978).
Carpino, L., "1-Hydroxy-7-azabenzotriazole. An Efficient Peptide Coupling Additive," J. Am. Chem. Soc. 1993, 115, pp. 4397-4398.
Carpino, et al., "Advantageous Applications of Azabenzotriazole (Triazolopyridine)-based Coupling Reagents to Solid-phase Peptide Synthesis," J. Chem. Soc., Chem. Commun. 1994, pp. 201-203.
Carpino, et al., "Racemization Studies During Solid-Phase Peptide Synthesis Using Azabenzotriazole-Based Coupling Regeants," Tetrahedron Letters 1994, 35, pp. 2279-2282.
Ehrlich, et al., "Synthesis of Cyclic Peptides via Efficient New Coupling Reagents," Tetrahedon Letters 1994, 34, pp. 4781-4784.
Kundu, et al., "Racemization studies with 1 (.beta.-naphthalenesulfonhyloxy)-benzotriazole (NSBT)--An Efficient peptide coupling reagent," Indian Journal of Chemistry 1989, 28B, pp. 604-605.

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