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Fmoc-L-HfLeu-OH

Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-5,5,5,5',5',5'-hexafluoro-L-leucine // Synonyms: (S)-Fmoc-2-amino-5,5,5-trifluoro-4-(trifluoromethyl)pentanoic acid, Fmoc-L-5,5,5,5’,5’,5’-hexafluoroleucine, Fmoc-L-Leu(F6)-OH, Fmoc-L-hexafluoroleucine, Fmoc-hexafluoroleucine, (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5,5,5-trifluoro-4-(trifluoromethyl)pentanoic acid

Product code:FAA8130
CAS No.:918667-71-7
Formula:C21H17F6NO4
Molecular weight:461,36 g/mol
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references

Effects of single substitutions with hexafluoroleucine and trifluorovaline on the hydrophobic core formation of a heterodimeric coiled coil; S. Huhmann, E. K. Nyakatura, H. Erdbrink, U. I. M. Gerling, C. Czekelius and B. Koksch; Journal of Fluorine Chemistry 2015; 175: 32-35. https://doi.org/10.1016/j.jfluchem.2015.03.003

Fluorinated proteins: from design and synthesis to structure and stability; E. N. Marsh; Acc Chem Res 2014; 47: 2878-86. https://doi.org/10.1021/ar500125m

Cross-strand interactions of fluorinated amino acids in beta-hairpin constructs; G. A. Clark, J. D. Baleja and K. Kumar; J Am Chem Soc 2012; 134: 17912-21. https://doi.org/10.1021/ja212080f

Influence of fluorination on the thermodynamics of protein folding; B. C. Buer, B. J. Levin and E. N. Marsh; J Am Chem Soc 2012; 134: 13027-34. https://doi.org/10.1021/ja303521h

Effect of highly fluorinated amino acids on protein stability at a solvent-exposed position on an internal strand of protein G B1 domain; H. P. Chiu, B. Kokona, R. Fairman and R. P. Cheng; J Am Chem Soc 2009; 131: 13192-3. https://doi.org/10.1021/ja903631h

Influence of selective fluorination on the biological activity and proteolytic stability of glucagon-like peptide-1; H. Meng, S. T. Krishnaji, M. Beinborn and K. Kumar; Journal of medicinal chemistry 2008; 51: 7303-7. https://doi.org/10.1021/jm8008579

Using fluorous amino acids to modulate the biological activity of an antimicrobial peptide; L. M. Gottler, H. Y. Lee, C. E. Shelburne, A. Ramamoorthy and E. N. Marsh; Chembiochem : a European journal of chemical biology 2008; 9: 370-3. https://doi.org/10.1002/cbic.200700643

Modulating protein structure with fluorous amino acids: increased stability and native-like structure conferred on a 4-helix bundle protein by hexafluoroleucine; H. Y. Lee, K. H. Lee, H. M. Al-Hashimi and E. N. Marsh; J Am Chem Soc 2006; 128: 337-43. https://doi.org/10.1021/ja0563410

Helix propensity of highly fluorinated amino acids; H. P. Chiu, Y. Suzuki, D. Gullickson, R. Ahmad, B. Kokona, R. Fairman and R. P. Cheng; J Am Chem Soc 2006; 128: 15556-7. https://doi.org/10.1021/ja0640445

Synthesis and thermodynamic characterization of self-sorting coiled coils; B. Bilgiçer and K. Kumar; Tetrahedron 2002; 58: 4105-4112. https://doi.org/10.1016/s0040-4020(02)00260-0

Biosynthesis of a highly stable coiled-coil protein containing hexafluoroleucine in an engineered bacterial host; Y. Tang and D. A. Tirrell; J Am Chem Soc 2001; 123: 11089-90. https://doi.org/10.1021/ja016652k

Programmed self-sorting of coiled coils with leucine and hexafluoroleucine cores; B. Bilgicer, X. Xing and K. Kumar; J Am Chem Soc 2001; 123: 11815-6. https://doi.org/10.1021/ja016767o

Fluorinated Coiled-Coil Proteins Prepared In Vivo Display Enhanced Thermal and Chemical Stability; Y. Tang, G. Ghirlanda, W. A. Petka, T. Nakajima, W. F. DeGrado and D. A. Tirrell; Angewandte Chemie International Edition 2001; 40: 1494-1496. https://doi.org/10.1002/1521-3773(20010417)40:8<1494::Aid-anie1494>3.0.Co;2-x

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