메뉴 건너뛰기




Volumn 117, Issue 30, 2013, Pages 8987-8993

Sensitive, site-specific, and stable vibrational probe of local protein environments: 4-azidomethyl- l -phenylalanine

Author keywords

[No Author keywords available]

Indexed keywords

AMBER CODONS; EXTINCTION COEFFICIENTS; GREEN FLUORESCENT PROTEIN; LOCAL ENVIRONMENTS; PHOTO-STABILITY; SITE-SPECIFIC; STRETCH VIBRATIONS; UNNATURAL AMINO ACIDS;

EID: 84881264139     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp4052598     Document Type: Article
Times cited : (45)

References (47)
  • 1
    • 33749019097 scopus 로고    scopus 로고
    • A Chemical Toolkit for Proteins - An Expanded Genetic Code
    • Xie, J.; Schultz, P. G. A Chemical Toolkit for Proteins-An Expanded Genetic Code Nat. Rev. Mol. Cell Biol. 2006, 7, 775-782
    • (2006) Nat. Rev. Mol. Cell Biol. , vol.7 , pp. 775-782
    • Xie, J.1    Schultz, P.G.2
  • 2
    • 80054955089 scopus 로고    scopus 로고
    • Site-Specific Spectroscopic Reporters of the Local Electric Field, Hydration, Structure, and Dynamics of Biomolecules
    • Waegele, M. M.; Culik, R. M.; Gai, F. Site-Specific Spectroscopic Reporters of the Local Electric Field, Hydration, Structure, and Dynamics of Biomolecules J. Phys. Chem. Lett. 2011, 2, 2598-2609
    • (2011) J. Phys. Chem. Lett. , vol.2 , pp. 2598-2609
    • Waegele, M.M.1    Culik, R.M.2    Gai, F.3
  • 4
    • 70349781906 scopus 로고    scopus 로고
    • Interpretation of p -Cyanophenylalanine Fluorescence in Proteins in Terms of Solvent Exposure and Contribution of Side-Chain Quenchers: A Combined Fluorescence, IR and Molecular Dynamics Study
    • Taskent-Sezgin, H.; Chung, J.; Patsalo, V.; Miyake-Stoner, S. J.; Miller, A. M.; Brewer, S. H.; Mehl, R. A.; Green, D. F.; Raleigh, D. P.; Carrico, I. Interpretation of p -Cyanophenylalanine Fluorescence in Proteins in Terms of Solvent Exposure and Contribution of Side-Chain Quenchers: A Combined Fluorescence, IR and Molecular Dynamics Study Biochemistry 2009, 48, 9040-9046
    • (2009) Biochemistry , vol.48 , pp. 9040-9046
    • Taskent-Sezgin, H.1    Chung, J.2    Patsalo, V.3    Miyake-Stoner, S.J.4    Miller, A.M.5    Brewer, S.H.6    Mehl, R.A.7    Green, D.F.8    Raleigh, D.P.9    Carrico, I.10
  • 5
    • 84865974861 scopus 로고    scopus 로고
    • Expanding the Utility of 4-Cyano-L-Phenylalanine as a Vibrational Reporter of Protein Environments
    • Bazewicz, C. G.; Lipkin, J. S.; Smith, E. E.; Liskov, M. T.; Brewer, S. H. Expanding the Utility of 4-Cyano-L-Phenylalanine as a Vibrational Reporter of Protein Environments J. Phys. Chem. B 2012, 116, 10824-10831
    • (2012) J. Phys. Chem. B , vol.116 , pp. 10824-10831
    • Bazewicz, C.G.1    Lipkin, J.S.2    Smith, E.E.3    Liskov, M.T.4    Brewer, S.H.5
  • 6
    • 67349121748 scopus 로고    scopus 로고
    • FTIR Analysis of GPCR Activation Using Azido Probes
    • Ye, S. X.; Huber, T.; Vogel, R.; Sakmar, T. P. FTIR Analysis of GPCR Activation Using Azido Probes Nat. Chem. Biol. 2009, 5, 397-399
    • (2009) Nat. Chem. Biol. , vol.5 , pp. 397-399
    • Ye, S.X.1    Huber, T.2    Vogel, R.3    Sakmar, T.P.4
  • 7
    • 77951877209 scopus 로고    scopus 로고
    • Tracking G-Protein-Coupled Receptor Activation Using Genetically Encoded Infrared Probes
    • Ye, S. X.; Zaitseva, E.; Caltabiano, G.; Schertler, G. F. X.; Sakmar, T. P.; Deupi, X.; Vogel, R. Tracking G-Protein-Coupled Receptor Activation Using Genetically Encoded Infrared Probes Nature 2010, 464, 1386-1389
    • (2010) Nature , vol.464 , pp. 1386-1389
    • Ye, S.X.1    Zaitseva, E.2    Caltabiano, G.3    Schertler, G.F.X.4    Sakmar, T.P.5    Deupi, X.6    Vogel, R.7
  • 8
    • 80053114546 scopus 로고    scopus 로고
    • Two-Dimensional IR Spectroscopy of Protein Dynamics Using Two Vibrational Labels: A Site-Specific Genetically Encoded Unnatural Amino Acid and an Active Site Ligand
    • Thielges, M. C.; Axup, J. Y.; Wong, D.; Lee, H. S.; Chung, J. K.; Schultz, P. G.; Fayer, M. D. Two-Dimensional IR Spectroscopy of Protein Dynamics Using Two Vibrational Labels: A Site-Specific Genetically Encoded Unnatural Amino Acid and an Active Site Ligand J. Phys. Chem. B 2011, 115, 11294-11304
    • (2011) J. Phys. Chem. B , vol.115 , pp. 11294-11304
    • Thielges, M.C.1    Axup, J.Y.2    Wong, D.3    Lee, H.S.4    Chung, J.K.5    Schultz, P.G.6    Fayer, M.D.7
  • 9
    • 0037438511 scopus 로고    scopus 로고
    • Using Nitrile-Derivatized Amino Acids as Infrared Probes of Local Environment
    • Getahun, Z.; Huang, C. Y.; Wang, T.; De Leon, B.; DeGrado, W. F.; Gai, F. Using Nitrile-Derivatized Amino Acids as Infrared Probes of Local Environment J. Am. Chem. Soc. 2003, 125, 405-411
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 405-411
    • Getahun, Z.1    Huang, C.Y.2    Wang, T.3    De Leon, B.4    Degrado, W.F.5    Gai, F.6
  • 13
    • 22944460826 scopus 로고    scopus 로고
    • Artificial Polypeptide Scaffold for Protein Immobilization
    • Zhang, K. C.; Diehl, M. R.; Tirrell, D. A. Artificial Polypeptide Scaffold for Protein Immobilization J. Am. Chem. Soc. 2005, 127, 10136-10137
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 10136-10137
    • Zhang, K.C.1    Diehl, M.R.2    Tirrell, D.A.3
  • 14
    • 15944403901 scopus 로고    scopus 로고
    • Conformational Distribution of a 14-Residue Peptide in Solution: A Fluorescence Resonance Energy Transfer Study
    • Tucker, M. J.; Oyola, R.; Gai, F. Conformational Distribution of a 14-Residue Peptide in Solution: A Fluorescence Resonance Energy Transfer Study J. Phys. Chem. B 2005, 109, 4788-4795
    • (2005) J. Phys. Chem. B , vol.109 , pp. 4788-4795
    • Tucker, M.J.1    Oyola, R.2    Gai, F.3
  • 15
    • 35649004824 scopus 로고    scopus 로고
    • Use of the Novel Fluorescent Amino Acid p -Cyanophenylalanine Offers a Direct Probe of Hydrophobic Core Formation during the Folding of the N-Terminal Domain of the Ribosomal Protein L9 and Provides Evidence for Two-State Folding
    • Aprilakis, K. N.; Taskent, H.; Raleigh, D. P. Use of the Novel Fluorescent Amino Acid p -Cyanophenylalanine Offers a Direct Probe of Hydrophobic Core Formation During the Folding of the N-Terminal Domain of the Ribosomal Protein L9 and Provides Evidence for Two-State Folding Biochemistry 2007, 46, 12308-12313
    • (2007) Biochemistry , vol.46 , pp. 12308-12313
    • Aprilakis, K.N.1    Taskent, H.2    Raleigh, D.P.3
  • 16
    • 54349127109 scopus 로고    scopus 로고
    • Using an Amino Acid Fluorescence Resonance Energy Transfer Pair to Probe Protein Unfolding: Application to the Villin Headpiece Subdomain and the LysM Domain
    • Glasscock, J. M.; Zhu, Y. J.; Chowdhury, P.; Tang, J.; Gai, F. Using an Amino Acid Fluorescence Resonance Energy Transfer Pair to Probe Protein Unfolding: Application to the Villin Headpiece Subdomain and the LysM Domain Biochemistry 2008, 47, 11070-11076
    • (2008) Biochemistry , vol.47 , pp. 11070-11076
    • Glasscock, J.M.1    Zhu, Y.J.2    Chowdhury, P.3    Tang, J.4    Gai, F.5
  • 17
    • 67649588679 scopus 로고    scopus 로고
    • Probing Protein Folding Using Site-Specifically Encoded Unnatural Amino Acids as FRET Donors with Tryptophan
    • Miyake-Stoner, S. J.; Miller, A. M.; Hammill, J. T.; Peeler, J. C.; Hess, K. R.; Mehl, R. A.; Brewer, S. H. Probing Protein Folding Using Site-Specifically Encoded Unnatural Amino Acids as FRET Donors with Tryptophan Biochemistry 2009, 48, 5953-5962
    • (2009) Biochemistry , vol.48 , pp. 5953-5962
    • Miyake-Stoner, S.J.1    Miller, A.M.2    Hammill, J.T.3    Peeler, J.C.4    Hess, K.R.5    Mehl, R.A.6    Brewer, S.H.7
  • 19
    • 0031717267 scopus 로고    scopus 로고
    • An Improved Preparation of 4-Hydroxymethyl- l -Phenylalanine
    • Morera, E.; Ortar, G.; Varani, A. An Improved Preparation of 4-Hydroxymethyl- l -Phenylalanine Synth. Commun. 1998, 28, 4279-4285
    • (1998) Synth. Commun. , vol.28 , pp. 4279-4285
    • Morera, E.1    Ortar, G.2    Varani, A.3
  • 20
    • 81255195897 scopus 로고    scopus 로고
    • Synthesis of Isotopomers of N -(tert -Butoxycarbonyl)-4-Cyano- l -Phenylalanine Methyl Ester: Choice of Cyanation Solvent
    • Bazewicz, C. G.; Lipkin, J. S.; Lozinak, K. A.; Watson, M. D.; Brewer, S. H. Synthesis of Isotopomers of N -(tert -Butoxycarbonyl)-4-Cyano- l -Phenylalanine Methyl Ester: Choice of Cyanation Solvent Tetrahedron Lett. 2011, 52, 6865-6868
    • (2011) Tetrahedron Lett. , vol.52 , pp. 6865-6868
    • Bazewicz, C.G.1    Lipkin, J.S.2    Lozinak, K.A.3    Watson, M.D.4    Brewer, S.H.5
  • 22
    • 33751391090 scopus 로고
    • A Simple Asymmetric-Synthesis of 4-Arylphenylalanines via Palladium-Catalyzed Cross-Coupling Reaction of Arylboronic Acids with Tyrosine Triflate
    • Shieh, W. C.; Carlson, J. A. A Simple Asymmetric-Synthesis of 4-Arylphenylalanines via Palladium-Catalyzed Cross-Coupling Reaction of Arylboronic Acids with Tyrosine Triflate J. Org. Chem. 1992, 57, 379-381
    • (1992) J. Org. Chem. , vol.57 , pp. 379-381
    • Shieh, W.C.1    Carlson, J.A.2
  • 24
    • 79952589680 scopus 로고    scopus 로고
    • Probing Local Environments with the Infrared Probe: L -4-Nitrophenylalanine
    • Smith, E. E.; Linderman, B. Y.; Luskin, A. C.; Brewer, S. H. Probing Local Environments with the Infrared Probe: l -4-Nitrophenylalanine J. Phys. Chem. B 2011, 115, 2380-2385
    • (2011) J. Phys. Chem. B , vol.115 , pp. 2380-2385
    • Smith, E.E.1    Linderman, B.Y.2    Luskin, A.C.3    Brewer, S.H.4
  • 25
    • 51049094425 scopus 로고    scopus 로고
    • β-Azidoalanine as an IR Probe: Application to Amyloid Aβ(16-22) Aggregation
    • Oh, K. I.; Lee, J. H.; Joo, C.; Han, H.; Cho, M. β-Azidoalanine as an IR Probe: Application to Amyloid Aβ(16-22) Aggregation J. Phys. Chem. B 2008, 112, 10352-10357
    • (2008) J. Phys. Chem. B , vol.112 , pp. 10352-10357
    • Oh, K.I.1    Lee, J.H.2    Joo, C.3    Han, H.4    Cho, M.5
  • 27
    • 77953388274 scopus 로고    scopus 로고
    • A Sensitive Multispectroscopic Probe for Nucleic Acids
    • Gai, X. S.; Fenlon, E. E.; Brewer, S. H. A Sensitive Multispectroscopic Probe for Nucleic Acids J. Phys. Chem. B 2010, 114, 7958-7966
    • (2010) J. Phys. Chem. B , vol.114 , pp. 7958-7966
    • Gai, X.S.1    Fenlon, E.E.2    Brewer, S.H.3
  • 28
    • 83755162489 scopus 로고    scopus 로고
    • Differential Ordering of the Protein Backbone and Side Chains during Protein Folding Revealed by Site-Specific Recombinant Infrared Probes
    • Nagarajan, S.; Taskent-Sezgin, H.; Parul, D.; Carrico, I.; Raleigh, D. P.; Dyer, R. B. Differential Ordering of the Protein Backbone and Side Chains During Protein Folding Revealed by Site-Specific Recombinant Infrared Probes J. Am. Chem. Soc. 2011, 133, 20335-20340
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 20335-20340
    • Nagarajan, S.1    Taskent-Sezgin, H.2    Parul, D.3    Carrico, I.4    Raleigh, D.P.5    Dyer, R.B.6
  • 30
    • 43449136205 scopus 로고    scopus 로고
    • Coherent Two-Dimensional Optical Spectroscopy
    • Cho, M. H. Coherent Two-Dimensional Optical Spectroscopy Chem. Rev. 2008, 108, 1331-1418
    • (2008) Chem. Rev. , vol.108 , pp. 1331-1418
    • Cho, M.H.1
  • 32
    • 66149084447 scopus 로고    scopus 로고
    • Two-Dimensional IR Spectroscopy and Isotope Labeling Defines the Pathway of Amyloid Formation with Residue-Specific Resolution
    • Shim, S. H.; Gupta, R.; Ling, Y. L.; Strasfeld, D. B.; Raleigh, D. P.; Zanni, M. T. Two-Dimensional IR Spectroscopy and Isotope Labeling Defines the Pathway of Amyloid Formation with Residue-Specific Resolution Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 6614-6619
    • (2009) Proc. Natl. Acad. Sci. U.S.A. , vol.106 , pp. 6614-6619
    • Shim, S.H.1    Gupta, R.2    Ling, Y.L.3    Strasfeld, D.B.4    Raleigh, D.P.5    Zanni, M.T.6
  • 33
    • 67149138048 scopus 로고    scopus 로고
    • Applications of 2D IR Spectroscopy to Peptides, Proteins, and Hydrogen-Bond Dynamics
    • Kim, Y. S.; Hochstrasser, R. M. Applications of 2D IR Spectroscopy to Peptides, Proteins, and Hydrogen-Bond Dynamics J. Phys. Chem. B 2009, 113, 8231-8251
    • (2009) J. Phys. Chem. B , vol.113 , pp. 8231-8251
    • Kim, Y.S.1    Hochstrasser, R.M.2
  • 34
    • 63749101949 scopus 로고    scopus 로고
    • 2D IR Photon Echo Study of the Anharmonic Coupling in the OCN Region of Phenyl Cyanate
    • Tucker, M. J.; Kim, Y. S.; Hochstrasser, R. M. 2D IR Photon Echo Study of the Anharmonic Coupling in the OCN Region of Phenyl Cyanate Chem. Phys. Lett. 2009, 470, 80-84
    • (2009) Chem. Phys. Lett. , vol.470 , pp. 80-84
    • Tucker, M.J.1    Kim, Y.S.2    Hochstrasser, R.M.3
  • 37
    • 79955687305 scopus 로고    scopus 로고
    • Two-Dimensional Infrared Study of 3-Azidopyridine as a Potential Spectroscopic Reporter of Protonation State
    • Nydegger, M. W.; Dutta, S.; Cheatum, C. M. Two-Dimensional Infrared Study of 3-Azidopyridine as a Potential Spectroscopic Reporter of Protonation State J. Chem. Phys. 2010, 133, 134506
    • (2010) J. Chem. Phys. , vol.133 , pp. 134506
    • Nydegger, M.W.1    Dutta, S.2    Cheatum, C.M.3
  • 38
    • 79952751750 scopus 로고    scopus 로고
    • Dynamics of the Folded and Unfolded Villin Headpiece (Hp35) Measured with Ultrafast 2D IR Vibrational Echo Spectroscopy
    • Chung, J. K.; Thielges, M. C.; Fayer, M. D. Dynamics of the Folded and Unfolded Villin Headpiece (Hp35) Measured with Ultrafast 2D IR Vibrational Echo Spectroscopy Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 3578-3583
    • (2011) Proc. Natl. Acad. Sci. U.S.A. , vol.108 , pp. 3578-3583
    • Chung, J.K.1    Thielges, M.C.2    Fayer, M.D.3
  • 40
    • 84859578791 scopus 로고    scopus 로고
    • Dynamics Measured Using a Nitrile Label with 2D IR Vibrational Echo Spectroscopy
    • Bagchi, S.; Boxer, S. G.; Fayer, M. D.; Ribonuclease, S. Dynamics Measured Using a Nitrile Label with 2D IR Vibrational Echo Spectroscopy J. Phys. Chem. B 2012, 116, 4034-4042
    • (2012) J. Phys. Chem. B , vol.116 , pp. 4034-4042
    • Bagchi, S.1    Boxer, S.G.2    Fayer, M.D.3    Ribonuclease, S.4
  • 41
    • 84862948033 scopus 로고    scopus 로고
    • 3-Picolyl Azide Adenine Dinucleotide as a Probe of Femtosecond to Picosecond Enzyme Dynamics
    • Dutta, S.; Li, Y. L.; Rock, W.; Houtman, J. C. D.; Kohen, A.; Cheatum, C. M. 3-Picolyl Azide Adenine Dinucleotide as a Probe of Femtosecond to Picosecond Enzyme Dynamics J. Phys. Chem. B 2012, 116, 542-548
    • (2012) J. Phys. Chem. B , vol.116 , pp. 542-548
    • Dutta, S.1    Li, Y.L.2    Rock, W.3    Houtman, J.C.D.4    Kohen, A.5    Cheatum, C.M.6
  • 42
    • 80051702554 scopus 로고    scopus 로고
    • Two-Dimensional Infrared Spectroscopy of Azido-Nicotinamide Adenine Dinucleotide in Water
    • Dutta, S.; Rock, W.; Cook, R. J.; Kohen, A.; Cheatum, C. M. Two-Dimensional Infrared Spectroscopy of Azido-Nicotinamide Adenine Dinucleotide in Water J. Chem. Phys. 2011, 135, 055106
    • (2011) J. Chem. Phys. , vol.135 , pp. 055106
    • Dutta, S.1    Rock, W.2    Cook, R.J.3    Kohen, A.4    Cheatum, C.M.5
  • 43
    • 84856385508 scopus 로고    scopus 로고
    • Covalently Bound Azido Groups Are Very Specific Water Sensors, even in Hydrogen-Bonding Environments
    • Wolfshorndl, M. P.; Baskin, R.; Dhawan, I.; Londergan, C. H. Covalently Bound Azido Groups Are Very Specific Water Sensors, Even in Hydrogen-Bonding Environments J. Phys. Chem. B 2012, 116, 1172-1179
    • (2012) J. Phys. Chem. B , vol.116 , pp. 1172-1179
    • Wolfshorndl, M.P.1    Baskin, R.2    Dhawan, I.3    Londergan, C.H.4
  • 44
    • 0001528720 scopus 로고    scopus 로고
    • Exact and Efficient Analytical Calculation of the Accessible Surface Areas and Their Gradients for Macromolecules
    • Fraczkiewicz, R.; Braun, W. Exact and Efficient Analytical Calculation of the Accessible Surface Areas and Their Gradients for Macromolecules J. Comput. Chem. 1998, 19, 319-333
    • (1998) J. Comput. Chem. , vol.19 , pp. 319-333
    • Fraczkiewicz, R.1    Braun, W.2
  • 45
    • 0000096835 scopus 로고    scopus 로고
    • Click Chemistry: Diverse Chemical Function from a Few Good Reactions
    • Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions Angew. Chem., Int. Ed. 2001, 40, 2004-2021
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, K.B.3
  • 46
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides
    • Tornoe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides J. Org. Chem. 2002, 67, 3057-3064
    • (2002) J. Org. Chem. , vol.67 , pp. 3057-3064
    • Tornoe, C.W.1    Christensen, C.2    Meldal, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.