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Volumn 48, Issue 45, 2009, Pages 10810-10817

Engineering protein stability and specificity using fluorous amino acids: The importance of packing effects

Author keywords

[No Author keywords available]

Indexed keywords

FLUOROUS; FOLDED PROTEINS; HELIX BUNDLE; HYDROPHOBIC AMINO ACIDS; HYDROPHOBIC CORE; PACKING EFFECTS; PHYSICOCHEMICAL PROPERTY; PROTEIN STABILITY; SIDE CHAINS; STABILIZING EFFECTS; THERMODYNAMICALLY STABLE;

EID: 70449562250     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi901481k     Document Type: Article
Times cited : (43)

References (30)
  • 1
    • 0028116495 scopus 로고
    • Facile catalyst separation without water: Fluorous biphase hydroformylation of olefins
    • Horvath, I. T., and Rabai, J. (1994) Facile catalyst separation without water: Fluorous biphase hydroformylation of olefins. Science 266, 72-75.
    • (1994) Science , vol.266 , pp. 72-75
    • Horvath, I.T.1    Rabai, J.2
  • 2
    • 0033912062 scopus 로고    scopus 로고
    • Towards the non-stick egg: Designing fluorous proteins
    • Marsh, E. N. G. (2000) Towards the non-stick egg: Designing fluorous proteins. Chem. Biol. 7, R153-R157.
    • (2000) Chem. Biol. , vol.7
    • Marsh, E.N.G.1
  • 3
    • 0035793878 scopus 로고    scopus 로고
    • Fluorous mixture synthesis: A fluorous-tagging strategy for the synthesis and separation of mixtures of organic compounds
    • DOI 10.1126/science.1057567
    • Luo, Z. Y., Zhang, Q. S., Oderaotoshi, Y., and Curran, D. P. (2001) Fluorous mixture synthesis: A fluorous-tagging strategy for the synthesis and separation of mixtures of organic compounds. Science 291, 1766-1769. (Pubitemid 32198977)
    • (2001) Science , vol.291 , Issue.5509 , pp. 1766-1769
    • Luo, Z.1    Zhang, Q.2    Oderaotoshi, Y.3    Curran, D.P.4
  • 4
    • 33751408183 scopus 로고    scopus 로고
    • Bioorthogonal noncovalent chemistry: Fluorous phases in chemical biology
    • Yoder, N. C., Yuksel, D., Dafik, L., and Kumar, K. (2006) Bioorthogonal noncovalent chemistry: Fluorous phases in chemical biology. Curr. Opin. Chem. Biol. 10, 576-583.
    • (2006) Curr. Opin. Chem. Biol. , vol.10 , pp. 576-583
    • Yoder, N.C.1    Yuksel, D.2    Dafik, L.3    Kumar, K.4
  • 5
    • 0036430153 scopus 로고    scopus 로고
    • Fluorinated amino acids in protein design and engineering
    • Yoder, N. C., and Kumar, K. (2002) Fluorinated amino acids in protein design and engineering. Chem. Soc. Rev. 31, 335-341.
    • (2002) Chem. Soc. Rev. , vol.31 , pp. 335-341
    • Yoder, N.C.1    Kumar, K.2
  • 6
    • 27644457086 scopus 로고    scopus 로고
    • Fluorine in peptide design and protein engineering
    • Jackel, C., and Koksch, B. (2005) Fluorine in peptide design and protein engineering. Eur. J. Org. Chem. 4483.
    • (2005) Eur. J. Org. Chem. , pp. 4483
    • Jackel, C.1    Koksch, B.2
  • 7
    • 33746593245 scopus 로고    scopus 로고
    • How C-α-fluoroalkyl amino acids and peptides interact with enzymes: Studies concerning the influence on proteolytic stability, enzymatic resolution and peptide coupling
    • Smits, R., and Koksch, B. (2006) How C-α-fluoroalkyl amino acids and peptides interact with enzymes: Studies concerning the influence on proteolytic stability, enzymatic resolution and peptide coupling. Curr. Top. Med. Chem. 6, 1483-1498.
    • (2006) Curr. Top. Med. Chem. , vol.6 , pp. 1483-1498
    • Smits, R.1    Koksch, B.2
  • 8
    • 0035965730 scopus 로고    scopus 로고
    • Programmed self-sorting of coiled coils with leucine and hexafluoroleucine cores
    • Bilgicer, B., Xing, X. C., and Kumar, K. (2001) Programmed self-sorting of coiled coils with leucine and hexafluoroleucine cores. J. Am. Chem. Soc. 123, 11815-11816.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 11815-11816
    • Bilgicer, B.1    Xing, X.C.2    Kumar, K.3
  • 9
    • 0034817253 scopus 로고    scopus 로고
    • A coiled coil with a fluorous core
    • Bilgicer, B., Fichera, A., and Kumar, K. (2001) A coiled coil with a fluorous core. J. Am. Chem. Soc. 123, 4393-4399.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 4393-4399
    • Bilgicer, B.1    Fichera, A.2    Kumar, K.3
  • 10
    • 0035823858 scopus 로고    scopus 로고
    • Biosynthesis of a highly stable coiled-coil protein containing hexafluoroleucine in an engineered bacterial host
    • Tang, Y., and Tirrell, D. A. (2001) Biosynthesis of a highly stable coiled-coil protein containing hexafluoroleucine in an engineered bacterial host. J. Am. Chem. Soc. 123, 11089-11090.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 11089-11090
    • Tang, Y.1    Tirrell, D.A.2
  • 11
    • 0034838165 scopus 로고    scopus 로고
    • Self-association and membrane-binding behavior of melittins containing trifluoroleucine
    • Niemz, A., and Tirrell, D. A. (2001) Self-association and membrane-binding behavior of melittins containing trifluoroleucine. J. Am. Chem. Soc. 123, 7407-7413.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 7407-7413
    • Niemz, A.1    Tirrell, D.A.2
  • 12
    • 0035901630 scopus 로고    scopus 로고
    • Fluorinated coiled-coil proteins prepared in vivo display enhanced thermal and chemical stability
    • DOI 10.1002/1521-3773(20010417)40:8<1494::AID-ANIE1494>3.0.CO;2-X
    • Tang, Y., Ghirlanda, G., Petka, W. A., Nakajima, T., DeGrado, W. F., and Tirrell, D. A. (2001) Fluorinated coiled-coil proteins prepared in vivo display enhanced thermal and chemical stability. Angew. Chem., Int. Ed. 40, 1494-1497. (Pubitemid 32367126)
    • (2001) Angewandte Chemie - International Edition , vol.40 , Issue.8 , pp. 1494-1496
    • Tang, Y.1    Ghirlanda, G.2    Petka, W.A.3    Nakajima, T.4    Degrado, W.F.5    Tirrell, D.A.6
  • 14
    • 0037071153 scopus 로고    scopus 로고
    • Synthesis and thermodynamic characterization of self-sorting coiled coils
    • DOI 10.1016/S0040-4020(02)00260-0, PII S0040402002002600
    • Bilgicer, B., and Kumar, K. (2002) Synthesis and thermodynamic characterization of self-sorting coiled coils. Tetrahedron 58, 4105-4112. (Pubitemid 34465683)
    • (2002) Tetrahedron , vol.58 , Issue.20 , pp. 4105-4112
    • Bilgicer, B.1    Kumar, K.2
  • 15
    • 11144320703 scopus 로고    scopus 로고
    • Fluorous effect in proteins: De novo design and characterization of a four-α-helix bundle protein containing hexafluoroleucine
    • Lee, K.-H., Lee, H.-Y., Slutsky, M. S., Anderson, J. T., and Marsh, E. N. G. (2004) Fluorous effect in proteins: De novo design and characterization of a four-α-helix bundle protein containing hexafluoroleucine. Biochemistry 43, 16277-16284.
    • (2004) Biochemistry , vol.43 , pp. 16277-16284
    • Lee, K.-H.1    Lee, H.-Y.2    Slutsky, M.S.3    Anderson, J.T.4    Marsh, E.N.G.5
  • 16
    • 30744471668 scopus 로고    scopus 로고
    • Modulating protein structure with fluorous amino acids: Increased stability and native-like structure conferred on a 4-helix bundle protein by hexafluoroleucine
    • Lee, H. Y., Lee, K. H., Al-Hashimi, H. M., and Marsh, E. N. G. (2006) Modulating protein structure with fluorous amino acids: Increased stability and native-like structure conferred on a 4-helix bundle protein by hexafluoroleucine. J. Am. Chem. Soc. 128, 337-343.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 337-343
    • Lee, H.Y.1    Lee, K.H.2    Al-Hashimi, H.M.3    Marsh, E.N.G.4
  • 19
    • 62649156942 scopus 로고    scopus 로고
    • Expanding the fluorous arsenal: Tetrafluorinated phenylalanines for protein design
    • Zheng, H., Comeforo, K., and Gao, J. (2009) Expanding the fluorous arsenal: Tetrafluorinated phenylalanines for protein design. J. Am. Chem. Soc. 131, 18-19.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 18-19
    • Zheng, H.1    Comeforo, K.2    Gao, J.3
  • 20
    • 33746320232 scopus 로고    scopus 로고
    • Fluorine in a native protein environment - How the spatial demand and polarity of fluoroalkyl groups affect protein folding
    • DOI 10.1002/anie.200504387
    • Jackel, C., Salwiczek, M., and Koksch, B. (2006) Fluorine in a native protein environment: How the spatial demand and polarity of fluoroalkyl groups affect protein folding. Angew. Chem., Int. Ed. 45, 4198-4203. (Pubitemid 44105684)
    • (2006) Angewandte Chemie - International Edition , vol.45 , Issue.25 , pp. 4198-4203
    • Jackel, C.1    Salwiczek, M.2    Koksch, B.3
  • 21
    • 7444241366 scopus 로고    scopus 로고
    • De novo design of defined helical bundles in membrane environments
    • Bilgicer, B., and Kumar, K. (2004) De novo design of defined helical bundles in membrane environments. Proc. Natl. Acad. Sci. U.S.A. 101, 15324-15329.
    • (2004) Proc. Natl. Acad. Sci. U.S.A. , vol.101 , pp. 15324-15329
    • Bilgicer, B.1    Kumar, K.2
  • 22
    • 33746302557 scopus 로고    scopus 로고
    • Fluorinated interfaces drive self-association of transmembrane R helices in lipid bilayers
    • DOI 10.1002/anie.200503567
    • Naarmann, N., Bilgicer, B., Meng, H., Kumar, K., and Steinem, C. (2006) Fluorinated interfaces drive self-association of transmembrane R helices in lipid bilayers. Angew. Chem., Int. Ed. 45, 2588-2591. (Pubitemid 44105767)
    • (2006) Angewandte Chemie - International Edition , vol.45 , Issue.16 , pp. 2588-2591
    • Naarmann, N.1    Bilgicer, B.2    Meng, H.3    Kumar, K.4    Steinem, C.5
  • 24
    • 0037191625 scopus 로고    scopus 로고
    • A short and efficient synthesis of L-5,5,5,5′,5′,5′- hexafluoroleucine from N-Cbz-L-serine
    • Anderson, J. T., Toogood, P. L., and Marsh, E. N. G. (2002) A short and efficient synthesis of L-5,5,5,5′,5′,5′-hexafluoroleucine from N-Cbz-L-serine. Org. Lett. 4, 4281-4283.
    • (2002) Org. Lett. , vol.4 , pp. 4281-4283
    • Anderson, J.T.1    Toogood, P.L.2    Marsh, E.N.G.3
  • 27
    • 15444374661 scopus 로고    scopus 로고
    • F-19: A versatile reporter for non-invasive physiology and pharmacology using magnetic resonance
    • Yu, J. X., Kodibagkar, V. D., Cui, W. N., and Mason, R. P. (2005) F-19: A versatile reporter for non-invasive physiology and pharmacology using magnetic resonance. Curr. Med. Chem. 12, 819-848.
    • (2005) Curr. Med. Chem. , vol.12 , pp. 819-848
    • Yu, J.X.1    Kodibagkar, V.D.2    Cui, W.N.3    Mason, R.P.4
  • 30
    • 0031029886 scopus 로고    scopus 로고
    • Fluorous synthesis: A fluorous-phase strategy for improving separation efficiency in organic synthesis
    • DOI 10.1126/science.275.5301.823
    • Studer, A., Hadida, S., Ferritto, R., Kim, S. Y., Jeger, P., Wipf, P., and Curran, D. P. (1997) Fluorous synthesis: A fluorous-phase strategy for improving separation efficiency in organic synthesis. Science 275, 823-826. (Pubitemid 27074881)
    • (1997) Science , vol.275 , Issue.5301 , pp. 823-826
    • Studer, A.1    Hadida, S.2    Ferritto, R.3    Kim, S.-Y.4    Jeger, P.5    Wipf, P.6    Curran, D.P.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.