Reagent useful for cleaving and process for using this reagent

Details Reagent useful for cleaving and process for using this reagent Reagent useful for cleaving and process for using this reagent

1994-10-31

1997-03-11

Woodward, Michael P.

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Synthesis of peptides

568716, A61K 3800, C07K 100

Patent

active

056102755

ABSTRACT:
The invention relates to a reagent which is useful for cleaving an alkoxycarbonyl group from a functional group which it is protecting and to a process for using this reagent. This reagent comprises a phenol, a diluent, and a hydrohalic or hydropseudohalic acid, the acidity of which is at least equal to that of formic acid. The method is advantageously applied in the synthesis of peptides.

REFERENCES:
A Cleavage Method Which Minimizes Side Reactions Following Fmoc Solid Phase Peptide Syntheses, King et al., International Journal of Peptide and Protein Research, 36:255-266 (1990).
Chlorotrimethylsilane-Phenol as a Mild Deprotection Reagent for the Tert-Butyl Based Protecting Groups in Peptide Synthesis, Kaiser et al., Tetrahedron Letters, 29(3):303-306 (1988).
Improved Selectivity in the Removal of the Tert-Butyloxycarbonyl Group, Bodanszky et al., Chemical Abstracts, 101:171728b (1984).
Deprotection of Carboxylic Esters of .beta.-Lactam Homologues. Cleavage of p-Methoxybenzyl, Diphenylmethyl, and Tert-Butyl Esters Effected by a Phenolic Matrix, Torii et al., Journal of Organic Chemistry, 56:3633-3637 (1991).
Ueki et al. Bull. Chem. Soc. Japan vol. 44, 1108-1111 (1971).
King et al. Int. J. Pept. Prot. Res. vol. 36 (1990) 255-266.
Torii et al. J. Org. Chem. (1991) pp. 3633-3637.
Kaiser et al. Tet. Lett. vol. 29 pp. 303-306 (1988).
Bodanszky et al. CA 101: 171728b (1984).
Stewart & Young, Solid Phase Peptide Syntheses (2nd ed.) (Pierce 1984) p. 5 .

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