Non-racemic trifluoroleucine, and methods of making and using

Details Non-racemic trifluoroleucine, and methods of making and using Non-racemic trifluoroleucine, and methods of making and using

2006-11-06

2008-05-13

Keys, Rosalynd (Department: 1621)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C558S256000, C560S019000, C560S043000, C560S047000, C560S048000, C560S155000, C560S156000, C560S172000, C562S433000, C562S450000, C562S456000, C562S457000, C562S553000

Reexamination Certificate

active

07371867

ABSTRACT:
One aspect of the invention relates to hexafluoroleucine and congeners thereof, and methods of making the compounds. Another aspect of the invention relates to the synthesis of protein cores comprising hexafluoroleucine and congeners thereof. Certain peptides comprising hexafluoroleucine and congeners thereof have been characterized using comparative biophysical studies. In general, the fluorinated peptides show higher thermal stability and enhanced resistance to chemical denaturation. Further, mixed hydrocarbon-fluorocarbon cores self-sort into homogeneous bundles, suggesting new avenues for the design and manipulation of protein-protein interfaces.

REFERENCES:
patent: 2004/0214988 (2004-10-01), Tirrell et al.
Taguchi et al., Jun. 1986, Tetrahedron Letters, vol. 27, No. 42, pp. 5117-5120.
Koksch, B. et al., “Proteolytically stable peptides by incorporation of a α-Tfm amino acids”,Journal of Peptide Science, 3:156-167 (European Peptide Society and John Wiley & Sons, Ltd.)(1997).
International Search Report dated Sep. 11, 2007.

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