Literature DB >> 26499242

Expanding the scope of alkyne-mediated bioconjugations utilizing unnatural amino acids.

Johnathan C Maza1, Zachary M Nimmo1, Douglas D Young1.   

Abstract

The importance of bioconjugates within the field of chemistry drives the need for novel methodologies for their preparation. Well-defined and stable bioconjugates are easily accessible via the utilization of unnatural amino acids (UAAs). As such, we have synthesized and incorporated two new UAAs into green fluorescent protein, and optimized a novel Cadiot-Chodkiewicz bioconjugation, effectively expanding the toolbox of chemical reactions that can be employed in the preparation of bioconjugates.

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Year:  2016        PMID: 26499242      PMCID: PMC5461652          DOI: 10.1039/c5cc08287k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  31 in total

Review 1.  Adding new chemistries to the genetic code.

Authors:  Chang C Liu; Peter G Schultz
Journal:  Annu Rev Biochem       Date:  2010       Impact factor: 23.643

2.  Cadiot-Chodkiewicz active template synthesis of rotaxanes and switchable molecular shuttles with weak intercomponent interactions.

Authors:  José Berná; Stephen M Goldup; Ai-Lan Lee; David A Leigh; Mark D Symes; Gilberto Teobaldi; Francesco Zerbetto
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 3.  Advances in enzyme immobilisation.

Authors:  Dean Brady; Justin Jordaan
Journal:  Biotechnol Lett       Date:  2009-07-10       Impact factor: 2.461

4.  Site-specific protein immobilization using unnatural amino acids.

Authors:  Benjamin K Raliski; Christina A Howard; Douglas D Young
Journal:  Bioconjug Chem       Date:  2014-10-29       Impact factor: 4.774

5.  Synthetase polyspecificity as a tool to modulate protein function.

Authors:  Douglas D Young; Steffen Jockush; Nicholas J Turro; Peter G Schultz
Journal:  Bioorg Med Chem Lett       Date:  2011-10-08       Impact factor: 2.823

Review 6.  Synthesis of naturally occurring polyynes.

Authors:  Annabelle L K Shi Shun; Rik R Tykwinski
Journal:  Angew Chem Int Ed Engl       Date:  2006-02-06       Impact factor: 15.336

Review 7.  Cu-free click cycloaddition reactions in chemical biology.

Authors:  John C Jewett; Carolyn R Bertozzi
Journal:  Chem Soc Rev       Date:  2010-04       Impact factor: 54.564

8.  Presentation and detection of azide functionality in bacterial cell surface proteins.

Authors:  A James Link; Mandy K S Vink; David A Tirrell
Journal:  J Am Chem Soc       Date:  2004-09-01       Impact factor: 15.419

9.  Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition.

Authors:  Qian Wang; Timothy R Chan; Robert Hilgraf; Valery V Fokin; K Barry Sharpless; M G Finn
Journal:  J Am Chem Soc       Date:  2003-03-19       Impact factor: 15.419

10.  A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems.

Authors:  Nicholas J Agard; Jennifer A Prescher; Carolyn R Bertozzi
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419

View more
  5 in total

1.  Utilization of alkyne bioconjugations to modulate protein function.

Authors:  Johnathan C Maza; Christina A Howard; Megha A Vipani; Christopher R Travis; Douglas D Young
Journal:  Bioorg Med Chem Lett       Date:  2016-11-16       Impact factor: 2.823

2.  Synthesis and incorporation of a caged tyrosine amino acid possessing a bioorthogonal handle.

Authors:  Marshall S Padilla; Christopher A Farley; Lindsay E Chatkewitz; Douglas D Young
Journal:  Tetrahedron Lett       Date:  2016-09-10       Impact factor: 2.415

3.  Development of optimized conditions for Glaser-Hay bioconjugations.

Authors:  Zachary M Nimmo; John F Halonski; Lindsay E Chatkewitz; Douglas D Young
Journal:  Bioorg Chem       Date:  2017-12-05       Impact factor: 5.275

4.  Mechanistic investigation and further optimization of the aqueous Glaser-Hay bioconjugation.

Authors:  Christopher R Travis; Lauren E Mazur; Emily M Peairs; Gillian H Gaunt; Douglas D Young
Journal:  Org Biomol Chem       Date:  2019-03-27       Impact factor: 3.876

Review 5.  Playing with the Molecules of Life.

Authors:  Douglas D Young; Peter G Schultz
Journal:  ACS Chem Biol       Date:  2018-03-02       Impact factor: 5.100

  5 in total

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