The DOI matches its Crossref record; 2 of the 2 references it cites were found in a registry or an index.
A Coiled Coil with a Fluorous Core
Abstract
The design, synthesis, and structural characterization of a highly fluorinated peptide system based on the coiled coil region of the yeast transcription factor GCN4 is described. All four leucine residues (a position) and three valine residues (d position) were replaced by the unnatural amino acids 5,5,5-trifluoroleucine and 4,4,4-trifluorovaline, respectively. The peptide is highly alpha-helical at low micromolar concentrations as judged by circular dichroism spectra, sediments as a dimeric species in the 5-30 microM concentration range, and exhibits a dimer melting temperature that is 15 degrees C higher than a control peptide with a hydrocarbon core. Furthermore, the apparent free energy of unfolding as calculated from guanidinium hydrochloride denaturation experiments is larger by approximately 1.0 kcal/mol for the fluorinated peptide than its hydrocarbon counterpart. We conclude that additional stability is derived from sequestering the more hydrophobic trifluoromethyl groups from aqueous solvent. These studies introduce a new paradigm in the design of molecular self-assembling systems, one based on orthogonal solubility properties of liquid phases.
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Citations
Cites
A Switch Between Two-, Three-, and Four-stranded Coiled Coils in GCN4 Leucine Zipper Mutants
Harbury, P. B., Zhang, T., Kim, P. S., & Alber, T. (1993) · Science · doi:10.1126/science.8248779 · Cited by 1,490
The Hydrophobic Effect and the Organization of Living Matter
Tanford, C. (1978) · Science · doi:10.1126/science.653353 · Cited by 985
Cited by
The Design of Coiled-Coil Structures and Assemblies
Woolfson, D. N. (2005) · Advances in Protein Chemistry · doi:10.1016/s0065-3233(05)70004-8 · Cited by 585
Non-canonical amino acids in protein engineering
Link, A. J., Mock, M. L., & Tirrell, D. A. (2003) · Current Opinion in Biotechnology · doi:10.1016/j.copbio.2003.10.011 · Cited by 393
Fluorinated amino acids in protein design and engineering
Yoder, N. C., & Kumar, K. (2002) · Chemical Society Reviews · doi:10.1039/b201097f · Cited by 317
Self-citationFluorous phase chemistry: a new industrial technology
Dobbs, A. P., & Kimberley, M. R. (2002) · Journal of Fluorine Chemistry · doi:10.1016/s0022-1139(02)00202-6 · Cited by 131
Non‐Canonical Amino Acids in Protein Polymer Design
Connor, R. E., & Tirrell, D. A. (2007) · Polymer Reviews · doi:10.1080/15583720601109552 · Cited by 103
Metadata
- Authors
- Bilgiçer, B., Fichera, A., & Kumar, K.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2001-04-12
- Volume
- 123
- Issue
- 19
- Pages
- 4393-4399
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2018525038
- Cited by
- 164
- References
- 2
- FWCI
- 3.37
- Type
- journal article
- Language
- en
- Open access
- closed
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