Literature DB >> 22731895

Design, synthesis, and photochemical validation of peptide linchpins containing the S,S-tetrazine phototrigger.

Mohannad Abdo1, Stephen P Brown, Joel R Courter, Matthew J Tucker, Robin M Hochstrasser, Amos B Smith.   

Abstract

The design, solid-phase synthesis, and photochemical validation of diverse peptide linchpins, containing the S,S-tetrazine phototrigger, have been achieved. Steady state irradiation or femtosecond laser pulses confirm their rapid photofragmentation. Attachment of peptides to the C- and N-termini will provide access to diverse constrained peptide constructs that hold the promise of providing information about early peptide/protein conformational dynamics upon photochemical release.

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Year:  2012        PMID: 22731895      PMCID: PMC3397404          DOI: 10.1021/ol301490h

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  18 in total

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Journal:  J Mol Biol       Date:  2000-07-21       Impact factor: 5.469

2.  Measuring the refolding of beta-sheets with different turn sequences on a nanosecond time scale.

Authors:  Rita P-Y Chen; Joseph J-T Huang; Hsin-Liang Chen; Howard Jan; Marappan Velusamy; Chung-Tien Lee; Wunshain Fann; Randy W Larsen; Sunney I Chan
Journal:  Proc Natl Acad Sci U S A       Date:  2004-05-03       Impact factor: 11.205

3.  How fast-folding proteins fold.

Authors:  Kresten Lindorff-Larsen; Stefano Piana; Ron O Dror; David E Shaw
Journal:  Science       Date:  2011-10-28       Impact factor: 47.728

4.  Alpha-helix formation in a photoswitchable peptide tracked from picoseconds to microseconds by time-resolved IR spectroscopy.

Authors:  Jens Bredenbeck; Jan Helbing; Janet R Kumita; G Andrew Woolley; Peter Hamm
Journal:  Proc Natl Acad Sci U S A       Date:  2005-02-07       Impact factor: 11.205

5.  Watching hydrogen-bond dynamics in a beta-turn by transient two-dimensional infrared spectroscopy.

Authors:  Christoph Kolano; Jan Helbing; Mariusz Kozinski; Wolfram Sander; Peter Hamm
Journal:  Nature       Date:  2006-11-23       Impact factor: 49.962

6.  Single-molecule fluorescence experiments determine protein folding transition path times.

Authors:  Hoi Sung Chung; Kevin McHale; John M Louis; William A Eaton
Journal:  Science       Date:  2012-02-24       Impact factor: 47.728

7.  Tetrazine phototriggers: probes for peptide dynamics.

Authors:  Matthew J Tucker; Joel R Courter; Jianxin Chen; Onur Atasoylu; Amos B Smith; Robin M Hochstrasser
Journal:  Angew Chem Int Ed Engl       Date:  2010-05-10       Impact factor: 15.336

8.  Three-dimensional structures by two-dimensional vibrational spectroscopy.

Authors:  Amanda Remorino; Robin M Hochstrasser
Journal:  Acc Chem Res       Date:  2012-03-29       Impact factor: 22.384

Review 9.  The folding of single domain proteins--have we reached a consensus?

Authors:  Tobin R Sosnick; Doug Barrick
Journal:  Curr Opin Struct Biol       Date:  2010-12-06       Impact factor: 6.809

10.  Intramolecular disulfide bridges as a phototrigger to monitor the dynamics of small cyclic peptides.

Authors:  Christoph Kolano; Jan Helbing; Götz Bucher; Wolfram Sander; Peter Hamm
Journal:  J Phys Chem B       Date:  2007-09-01       Impact factor: 2.991

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  7 in total

Review 1.  Arylation Chemistry for Bioconjugation.

Authors:  Chi Zhang; Ekaterina V Vinogradova; Alexander M Spokoyny; Stephen L Buchwald; Bradley L Pentelute
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-15       Impact factor: 15.336

2.  Nonequilibrium dynamics of helix reorganization observed by transient 2D IR spectroscopy.

Authors:  Matthew J Tucker; Mohannad Abdo; Joel R Courter; Jianxin Chen; Stephen P Brown; Amos B Smith; Robin M Hochstrasser
Journal:  Proc Natl Acad Sci U S A       Date:  2013-10-08       Impact factor: 11.205

3.  The design and synthesis of alanine-rich α-helical peptides constrained by an S,S-tetrazine photochemical trigger: a fragment union approach.

Authors:  Joel R Courter; Mohannad Abdo; Stephen P Brown; Matthew J Tucker; Robin M Hochstrasser; Amos B Smith
Journal:  J Org Chem       Date:  2013-12-20       Impact factor: 4.354

4.  Convergent diversity-oriented side-chain macrocyclization scan for unprotected polypeptides.

Authors:  Yekui Zou; Alexander M Spokoyny; Chi Zhang; Mark D Simon; Hongtao Yu; Yu-Shan Lin; Bradley L Pentelute
Journal:  Org Biomol Chem       Date:  2014-01-28       Impact factor: 3.876

5.  Peptide/protein stapling and unstapling: introduction of s-tetrazine, photochemical release, and regeneration of the peptide/protein.

Authors:  Stephen P Brown; Amos B Smith
Journal:  J Am Chem Soc       Date:  2015-03-20       Impact factor: 15.419

6.  Tetrazine as a general phototrigger to turn on fluorophores.

Authors:  Axel Loredo; Juan Tang; Lushun Wang; Kuan-Lin Wu; Zane Peng; Han Xiao
Journal:  Chem Sci       Date:  2020-04-07       Impact factor: 9.825

7.  Enhanced Permeability and Binding Activity of Isobutylene-Grafted Peptides.

Authors:  Shuang Sun; Ismael Compañón; Nuria Martínez-Sáez; João D Seixas; Omar Boutureira; Francisco Corzana; Gonçalo J L Bernardes
Journal:  Chembiochem       Date:  2017-11-22       Impact factor: 3.164

  7 in total

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