Fluorous capping reagents and methods for peptide purification

Details Fluorous capping reagents and methods for peptide purification Fluorous capping reagents and methods for peptide purification

2005-05-18

2009-11-03

Sullivan, Daniel M (Department: 1621)

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Separation or purification

C536S127000, C536S025400, C558S061000, C570S141000

Reexamination Certificate

active

07612166

ABSTRACT:
Aspects of the present invention relate to compounds for preparing fluorocarbon compounds, methods for preparing fluorocarbon compounds, and methods for purifying a mixture of compounds. One aspect of the present invention relates to a trivalent iodonium fluorocarbon. The trivalent iodonium fluorocarbon compound of the invention is useful for attaching a fluorocarbon group to a compound that has a nucleophilic functional group. Another aspect of the present invention relates to a method of preparing a trivalent iodonium fluorocarbon. Another aspect of the present invention relates to a method of preparing a fluorocarbon by treating a compound bearing a nucleophilic functional group with a trivalent iodonium fluorocarbon compound. Another aspect of the present invention relates to a method or purifying a mixture comprising a first and a second compound by treating the mixture with a trivalent iodonium fluorocarbon to attach a fluorocarbon group to the second compound leaving the first compound unchanged, and purifying the mixture by fluorous-phase purification.

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Zhang et al., Direct methylation and trifluoroethylation of imidazole and pyridine derivatives, Chemical Communications (Cambridge, United Kingdom) (2003), (18), 2334-2335.
DesMarteau et al., Easy preparation of bioactive peptides from the novel Na-trifluoroethyl amino acids, Chemistry Letters (2000), (9), 1052-1053.
DesMarteau et al., The first fluoroalkylation of amino acids and peptides in water utilizing the novel iodonium salt CF3SO2)2NI(Ph)CH2CF3, Chemical Communications (Cambridge) (1998), (20), 2241-2242.

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