Literature DB >> 33141139

Tyrosine bioconjugation - an emergent alternative.

Peter A Szijj1, Kristina A Kostadinova1, Richard J Spears1, Vijay Chudasama1.   

Abstract

Protein bioconjugation is an increasingly important field of research, with wide-ranging applications in areas such as therapeutics and biomaterials. Traditional cysteine and lysine bioconjugation strategies are widely used and have been extensively researched, but in some cases they are not appropriate and alternatives are needed or they are not compatible with one another to enable the formation of dually (and distinctly) modified dual-conjugates (an increasingly desired class of bioconjugates). Here we review the heretofore less explored approach of tyrosine bioconjugation, which is rapidly becoming a constructive alternative/complement to the more well-established strategies. Herein we present an overview of the field, and then focus on promising recent methods that can achieve high conversion and chemoselectivity. This suggests that not only can tyrosine bioconjugation be used in conjunction with cysteine and lysine modification to obtain proteins with multiple different modifications, it is also becoming a stand-alone alternative to these more traditional methods.

Entities:  

Mesh:

Substances:

Year:  2020        PMID: 33141139      PMCID: PMC7814872          DOI: 10.1039/d0ob01912g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  56 in total

1.  Chemistry of periodate-mediated cross-linking of 3,4-dihydroxylphenylalanine-containing molecules to proteins.

Authors:  Bo Liu; Lyle Burdine; Thomas Kodadek
Journal:  J Am Chem Soc       Date:  2006-11-29       Impact factor: 15.419

Review 2.  Advances in chemical protein modification.

Authors:  Omar Boutureira; Gonçalo J L Bernardes
Journal:  Chem Rev       Date:  2015-02-20       Impact factor: 60.622

Review 3.  Strategies and challenges for the next generation of antibody-drug conjugates.

Authors:  Alain Beck; Liliane Goetsch; Charles Dumontet; Nathalie Corvaïa
Journal:  Nat Rev Drug Discov       Date:  2017-03-17       Impact factor: 84.694

4.  Electrochemically Promoted Tyrosine-Click-Chemistry for Protein Labeling.

Authors:  Dimitri Alvarez-Dorta; Christine Thobie-Gautier; Mikael Croyal; Mohammed Bouzelha; Mathieu Mével; David Deniaud; Mohammed Boujtita; Sébastien G Gouin
Journal:  J Am Chem Soc       Date:  2018-11-28       Impact factor: 15.419

5.  Site-Selective Protein Chemical Modification of Exposed Tyrosine Residues Using Tyrosine Click Reaction.

Authors:  Shinichi Sato; Masaki Matsumura; Tetsuya Kadonosono; Satoshi Abe; Takafumi Ueno; Hiroshi Ueda; Hiroyuki Nakamura
Journal:  Bioconjug Chem       Date:  2020-04-13       Impact factor: 4.774

6.  Chemoselective Tyrosine Bioconjugation through Sulfate Click Reaction.

Authors:  Eun Joung Choi; Dongwook Jung; Jong-Seo Kim; Yan Lee; B Moon Kim
Journal:  Chemistry       Date:  2018-07-18       Impact factor: 5.236

7.  Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent.

Authors:  Tyler J Wadzinski; Angela Steinauer; Liana Hie; Guillaume Pelletier; Alanna Schepartz; Scott J Miller
Journal:  Nat Chem       Date:  2018-04-30       Impact factor: 24.427

8.  An Enzyme Cascade for Selective Modification of Tyrosine Residues in Structurally Diverse Peptides and Proteins.

Authors:  Anna-Winona Struck; Matthew R Bennett; Sarah A Shepherd; Brian J C Law; Ying Zhuo; Lu Shin Wong; Jason Micklefield
Journal:  J Am Chem Soc       Date:  2016-02-25       Impact factor: 15.419

9.  DNA-Catalyzed Introduction of Azide at Tyrosine for Peptide Modification.

Authors:  Puzhou Wang; Scott K Silverman
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-08       Impact factor: 15.336

10.  Site-Specific Bioconjugation through Enzyme-Catalyzed Tyrosine-Cysteine Bond Formation.

Authors:  Marco J Lobba; Christof Fellmann; Alan M Marmelstein; Johnathan C Maza; Elijah N Kissman; Stephanie A Robinson; Brett T Staahl; Cole Urnes; Rachel J Lew; Casey S Mogilevsky; Jennifer A Doudna; Matthew B Francis
Journal:  ACS Cent Sci       Date:  2020-08-21       Impact factor: 14.553

View more
  10 in total

Review 1.  Reactive chemistry for covalent probe and therapeutic development.

Authors:  R Justin Grams; Ku-Lung Hsu
Journal:  Trends Pharmacol Sci       Date:  2022-01-06       Impact factor: 14.819

Review 2.  Genetic and Covalent Protein Modification Strategies to Facilitate Intracellular Delivery.

Authors:  Justin M Horn; Allie C Obermeyer
Journal:  Biomacromolecules       Date:  2021-12-02       Impact factor: 6.978

3.  Copper-Free Click Enabled Triazabutadiene for Bioorthogonal Protein Functionalization.

Authors:  Anjalee N Wijetunge; Garrett J Davis; Mehrdad Shadmehr; Julia A Townsend; Michael T Marty; John C Jewett
Journal:  Bioconjug Chem       Date:  2021-01-25       Impact factor: 4.774

Review 4.  Hypervalent Iodine-Mediated Late-Stage Peptide and Protein Functionalization.

Authors:  Emmanuelle M D Allouche; Elija Grinhagena; Jerome Waser
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-08       Impact factor: 16.823

5.  Synthesis of Lasalocid-Based Bioconjugates and Evaluation of Their Anticancer Activity.

Authors:  Michał Antoszczak; Dagmara Otto-Ślusarczyk; Marta Kordylas; Marta Struga; Adam Huczyński
Journal:  ACS Omega       Date:  2022-01-07

6.  Luminol anchors improve the electrochemical-tyrosine-click labelling of proteins.

Authors:  Sébastien Depienne; Dimitri Alvarez-Dorta; Mikael Croyal; Ranil C T Temgoua; Cathy Charlier; David Deniaud; Mathieu Mével; Mohammed Boujtita; Sébastien G Gouin
Journal:  Chem Sci       Date:  2021-11-10       Impact factor: 9.825

7.  Retaining the structural integrity of disulfide bonds in diphtheria toxoid carrier protein is crucial for the effectiveness of glycoconjugate vaccine candidates.

Authors:  Filippo Carboni; Annabel Kitowski; Charlotte Sorieul; Daniele Veggi; Marta C Marques; Davide Oldrini; Evita Balducci; Barbara Brogioni; Linda Del Bino; Alessio Corrado; Francesca Angiolini; Lucia Dello Iacono; Immaculada Margarit; Maria Rosaria Romano; Gonçalo J L Bernardes; Roberto Adamo
Journal:  Chem Sci       Date:  2022-02-10       Impact factor: 9.825

8.  An Organometallic Strategy for Cysteine Borylation.

Authors:  Mary A Waddington; Xin Zheng; Julia M Stauber; Elamar Hakim Moully; Hayden R Montgomery; Liban M A Saleh; Petr Král; Alexander M Spokoyny
Journal:  J Am Chem Soc       Date:  2021-06-01       Impact factor: 16.383

9.  An overview of chemo- and site-selectivity aspects in the chemical conjugation of proteins.

Authors:  Charlotte Sornay; Valentine Vaur; Alain Wagner; Guilhem Chaubet
Journal:  R Soc Open Sci       Date:  2022-01-26       Impact factor: 2.963

10.  Late-Stage C-H Acylation of Tyrosine-Containing Oligopeptides with Alcohols.

Authors:  Iñaki Urruzuno; Paula Andrade-Sampedro; Arkaitz Correa
Journal:  Org Lett       Date:  2021-09-03       Impact factor: 6.005

  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.