Literature DB >> 21077670

Selective incorporation of nitrile-based infrared probes into proteins via cysteine alkylation.

Hyunil Jo1, Robert M Culik, Ivan V Korendovych, William F Degrado, Feng Gai.   

Abstract

The nitrile stretching vibration is increasingly used as a sensitive infrared probe of local protein environments. However, site-specific incorporation of a nitrile moiety into proteins is difficult. Here we show that various aromatic nitriles can be easily incorporated into peptides and proteins via either thiol alkylation or arylation reaction.

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Year:  2010        PMID： 21077670      PMCID： PMC2999665          DOI： 10.1021/bi101711a

Source DB:  PubMed          Journal:  Biochemistry        ISSN： 0006-2960            Impact factor:   3.162


  35 in total

1.  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.

Authors:  Humeyra Taskent-Sezgin; Juah Chung; Vadim Patsalo; Shigeki J Miyake-Stoner; Andrew M Miller; Scott H Brewer; Ryan A Mehl; David F Green; Daniel P Raleigh; Isaac Carrico
Journal:  Biochemistry       Date:  2009-09-29       Impact factor: 3.162

2.  Computational Modeling of the Nitrile Stretching Vibration of 5-Cyanoindole in Water.

Authors:  Matthias M Waegele; Feng Gai
Journal:  J Phys Chem Lett       Date:  2010-02-01       Impact factor: 6.475

3.  Solution structure of a calmodulin-target peptide complex by multidimensional NMR.

Authors:  M Ikura; G M Clore; A M Gronenborn; G Zhu; C B Klee; A Bax
Journal:  Science       Date:  1992-05-01       Impact factor: 47.728

4.  5-Cyanotryptophan as an Infrared Probe of Local Hydration Status of Proteins.

Authors:  Matthias M Waegele; Matthew J Tucker; Feng Gai
Journal:  Chem Phys Lett       Date:  2009-09-01       Impact factor: 2.328

5.  Residue-specific, real-time characterization of lag-phase species and fibril growth during amyloid formation: a combined fluorescence and IR study of p-cyanophenylalanine analogs of islet amyloid polypeptide.

Authors:  Peter Marek; Sudipta Mukherjee; Martin T Zanni; Daniel P Raleigh
Journal:  J Mol Biol       Date:  2010-06-01       Impact factor: 5.469

6.  Cyanylated Cysteine: A Covalently Attached Vibrational Probe of Protein-Lipid Contacts.

Authors:  Heather A McMahon; Katherine N Alfieri; Katherine A A Clark; Casey H Londergan
Journal:  J Phys Chem Lett       Date:  2010-02-12       Impact factor: 6.475

7.  Probing protein folding using site-specifically encoded unnatural amino acids as FRET donors with tryptophan.

Authors:  Shigeki J Miyake-Stoner; Andrew M Miller; Jared T Hammill; Jennifer C Peeler; Kenneth R Hess; Ryan A Mehl; Scott H Brewer
Journal:  Biochemistry       Date:  2009-06-30       Impact factor: 3.162

8.  Using nitrile-derivatized amino acids as infrared probes of local environment.

Authors:  Zelleka Getahun; Cheng-Yen Huang; Ting Wang; Brenda De León; William F DeGrado; Feng Gai
Journal:  J Am Chem Soc       Date:  2003-01-15       Impact factor: 15.419

9.  A combinatorial approach for the design of complementarity-determining region-derived peptidomimetics with in vitro anti-tumoral activity.

Authors:  Peter Timmerman; Rodrigo Barderas; Johan Desmet; Danièle Altschuh; Susana Shochat; Martine J Hollestelle; Jo W M Höppener; Alberto Monasterio; J Ignacio Casal; Rob H Meloen
Journal:  J Biol Chem       Date:  2009-10-06       Impact factor: 5.157

10.  Protein modification, bioconjugation, and disulfide bridging using bromomaleimides.

Authors:  Mark E B Smith; Felix F Schumacher; Chris P Ryan; Lauren M Tedaldi; Danai Papaioannou; Gabriel Waksman; Stephen Caddick; James R Baker
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419
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  16 in total

1.  Site-Specific Spectroscopic Reporters of the Local Electric Field, Hydration, Structure, and Dynamics of Biomolecules.

Authors:  Matthias M Waegele; Robert M Culik; Feng Gai
Journal:  J Phys Chem Lett       Date:  2011-09-23       Impact factor: 6.475

2.  Synthesis and Protein Incorporation of Azido-Modified Unnatural Amino Acids.

Authors:  Elise M Tookmanian; Edward E Fenlon; Scott H Brewer
Journal:  RSC Adv       Date:  2014-12-02       Impact factor: 3.361

3.  An alternative structural isoform in amyloid-like aggregates formed from thermally denatured human γD-crystallin.

Authors:  Sean D Moran; Tianqi O Zhang; Martin T Zanni
Journal:  Protein Sci       Date:  2014-02-04       Impact factor: 6.725

Review 4.  Site-specific infrared probes of proteins.

Authors:  Jianqiang Ma; Ileana M Pazos; Wenkai Zhang; Robert M Culik; Feng Gai
Journal:  Annu Rev Phys Chem       Date:  2015-01-12       Impact factor: 12.703

5.  Simple method to introduce an ester infrared probe into proteins.

Authors:  Ismail A Ahmed; Feng Gai
Journal:  Protein Sci       Date:  2017-01-14       Impact factor: 6.725

6.  Site-specific measurement of water dynamics in the substrate pocket of ketosteroid isomerase using time-resolved vibrational spectroscopy.

Authors:  Santosh Kumar Jha; Minbiao Ji; Kelly J Gaffney; Steven G Boxer
Journal:  J Phys Chem B       Date:  2012-09-07       Impact factor: 2.991

Review 7.  Minimalist IR and fluorescence probes of protein function.

Authors:  Pallavi M Gosavi; Ivan V Korendovych
Journal:  Curr Opin Chem Biol       Date:  2016-09-10       Impact factor: 8.822

8.  A direct comparison of azide and nitrile vibrational probes.

Authors:  Xin Sonia Gai; Basil A Coutifaris; Scott H Brewer; Edward E Fenlon
Journal:  Phys Chem Chem Phys       Date:  2011-02-18       Impact factor: 3.676

9.  A strongly absorbing class of non-natural labels for probing protein electrostatics and solvation with FTIR and 2D IR spectroscopies.

Authors:  Ann Marie Woys; Sudipta S Mukherjee; David R Skoff; Sean D Moran; Martin T Zanni
Journal:  J Phys Chem B       Date:  2013-04-15       Impact factor: 2.991

10.  Painting proteins blue: β-(1-azulenyl)-L-alanine as a probe for studying protein-protein interactions.

Authors:  Yurii S Moroz; Wolfgang Binder; Patrik Nygren; Gregory A Caputo; Ivan V Korendovych
Journal:  Chem Commun (Camb)       Date:  2013-01-18       Impact factor: 6.222
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