Towards the nonstick egg: Designing fluorous proteins

Chemistry and Biology

Volumn 7, Issue 7, 2000, Pages

  Neil, E ^a   Marsh, G ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CORYDALIS AUREA;

EID: 0033912062     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(00)00139-3     Document Type: Note

References (20)

1. Harper D.B., O'hagan D. The fluorinated natural-products. Natl Prod. Rep. 11:1994;123-133.
2. Gerig J.T. Fluorine NMR of proteins. Prog. NMR Spectrosc. 26:1994;293-370.
3. Eberhardt E.S., Panasik N., Raines R.T. Inductive effects on the energetics of prolyl peptide bond isomerization: implications for collagen folding and stability. J. Am. Chem. Soc. 118:1996;12261-12266.
4. Duewel H., Daub E., Robinson V., Honek J.F. Incorporation of trifluoromethionine into a phage lysozyme: implications and a new marker for use in protein F-19 NMR. Biochemistry. 36:1997;3404-3416.
5. Resnati G. Synthesis of chiral and bioactive fluoroorganic compounds. Tetrahedron. 49:1993;9385-9445.
6. Studer A., Curran D.P.et al. Fluorous synthesis: a fluorous-phase strategy for improving separation efficiency in organic synthesis. Science. 275:1997;823-826.
7. Zhang C., Ludin C., Eberle M.K., Stoeckli-Evans H., Keese R. Asymmetric synthesis of (S)-5,5,5,5′,5′,5′-hexafluoroleucine. Helv. Chim. Acta. 81:1998;174-181.
8. Eberle M.K., Keese R., Stoeckli-Evans H. New synthesis and chirality of (-)-4,4,4,4′,4′,4′-hexafluorovaline. Helv. Chim. Acta. 81:1998;182-186.
9. Houston M.E., Harvath L., Honek J.F. Synthesis of and chemotactic responses elicited by fMet-Leu-Phe analogs containing difluoro- and trifluoromethionine. Bioorg. Med. Chem. Lett. 7:1997;3007-3012.
10. Wilken J., Kent S.B.H. Chemical protein synthesis. Curr. Opin. Biotechnol. 9:1998;412-426.
11. Cotton G.J., Muir T.W. Peptide ligation and its application to protein engineering. Chem. Biol. 6:1999;R247-R256.
12. Cotton G.J., Ayers B., Xu R., Muir T.W. Insertion of a synthetic peptide into a recombinant protein framework: a protein biosensor. J. Am. Chem. Soc. 121:1999;1100-1101.
13. Chianelli M.S., Stella C.A., Saenz D.A., Ramos E.H., Kotliar N., Mattoon J.R. Isolation of a trifluoroleucine-resistant mutant of Saccharomyces cerevisiae deficient in both high- and low- affinity L-leucine transport. Cell. Mol. Biol. 42:1996;847-857.
14. Kothakota S., Dougherty M.J., Fournier M.J., Mason T.L., Yoshikawa E., Tirrell D.A. Templated biological synthesis of polymers of abiological monomers. Macromol. Symp. 98:1995;573-583.
15. Tang, Y. & Tirrell, D.A. (1999). Stabilization of leucine zipper coiled coils by introduction of trifluoroleucine. Abstr. Pap. Am. Chem. Soc. 3218, 416-ORGN.
16. Liu D.R., Schultz P.G. Progress toward the evolution of an organism with an expanded genetic code. Proc. Natl Acad. Sci. USA. 96:1999;4780-4785.
17. DeGrado W.F., Summa C.M., Pavone V., Nastri F., Lombardi A. De novo design and structural characterization of proteins and metalloproteins. Ann. Rev. Biochem. 68:1999;779-819.
18. Munson M., Regan L.et al. What makes a protein a protein? Hydrophobic core designs that specify stability and structural properties. Prot. Sci. 5:1996;1584-1593.
19. Hsieh K.H., Needleman P., Marshall G.R. Long-acting angiotensin-II inhibitors containing hexafluorovaline in position-8. J. Med. Chem. 30:1987;1097-1100.
20. O'shea E.K., Klemm J.D., Kim P.S., Alber T. X-Ray structure of the Gcn4 Leucine zipper, a 2-stranded, parallel coiled coil. Science. 254:1991;539-544.