BIOMAT Database Logo BIOMAT Database Logo

Cycloadditions of Trans-Cyclooctenes and Nitrones as Tools for Bioorthogonal Labelling. 2020

Kaitlyn D Margison, and Didier A Bilodeau, and Farnaz Mahmoudi, and John Paul Pezacki
Department of Chemistry and Biomolecular Sciences, University of Ottawa, 150 Louis-Pasteur, Ottawa, ON, K1N 6N5, Canada.

Trans-cyclooctenes (TCOs) represent interesting and highly reactive dipolarophiles for organic transformations including bioorthogonal chemistry. Herein we show that TCOs react rapidly with nitrones and that these reactions are bioorthogonal. Kinetic analysis of acyclic and cyclic nitrones with strained-trans-cyclooctene (s-TCO) shows fast reactivity and demonstrates the utility of this cycloaddition reaction for bioorthogonal labelling. Labelling of the bacterial peptidoglycan layer with unnatural d-amino acids tagged with nitrones and s-TCO-Alexa488 is demonstrated. These new findings expand the bioorthogonal toolbox, and allow TCO reagents to be used in bioorthogonal applications beyond tetrazine ligations for the first time and open up new avenues for bioorthogonal ligations with diverse nitrone reactants.

UI MeSH Term Description Entries
D007536 Isomerism The phenomenon whereby certain chemical compounds have structures that are different although the compounds possess the same elemental composition. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Isomerisms
D007700 Kinetics The rate dynamics in chemical or physical systems.
D009589 Nitrogen Oxides Inorganic oxides that contain nitrogen. Nitrogen Oxide,Oxide, Nitrogen,Oxides, Nitrogen
D010457 Peptidoglycan A structural polymer of the bacterial cell envelope consisting of sugars and amino acids which is responsible for both shape determination and cellular integrity under osmotic stress in virtually all bacteria. Murein,Pseudomurein
D006834 Hydrazines Substituted derivatives of hydrazine (formula H2N-NH2). Hydrazide
D061565 Cycloaddition Reaction Synthetic organic reactions that use reactions between unsaturated molecules to form cyclical products. Cycloaddition,Cycloaddition Reaction Techniques,Diels-Alder Reaction,Cycloaddition Reaction Technique,Cycloaddition Reactions,Diels Alder Reaction,Reaction Technique, Cycloaddition,Reaction Techniques, Cycloaddition,Reaction, Cycloaddition,Reaction, Diels-Alder,Reactions, Cycloaddition,Technique, Cycloaddition Reaction,Techniques, Cycloaddition Reaction
D034242 Cyclooctanes A group of compounds with an 8-carbon ring. They may be saturated or unsaturated. Benzocyclooctanes,Benzocyclooctenes,Cyclooctenes,Cyclooctodienes,Dibenzocyclooctanes

Related Publications

Kaitlyn D Margison, and Didier A Bilodeau, and Farnaz Mahmoudi, and John Paul Pezacki
Bioorthogonal Cycloadditions of C3-Trifluoromethylated 1,2,4-Triazines with trans-Cyclooctenes.
May 2024, Chemistry (Weinheim an der Bergstrasse, Germany),
Kaitlyn D Margison, and Didier A Bilodeau, and Farnaz Mahmoudi, and John Paul Pezacki
Predicting reactivity for bioorthogonal cycloadditions involving nitrones.
August 2020, RSC advances,
Kaitlyn D Margison, and Didier A Bilodeau, and Farnaz Mahmoudi, and John Paul Pezacki
Enhancing reactivity for bioorthogonal pretargeting by unmasking antibody-conjugated trans-cyclooctenes.
February 2015, Bioconjugate chemistry,
Kaitlyn D Margison, and Didier A Bilodeau, and Farnaz Mahmoudi, and John Paul Pezacki
Strain-promoted cycloadditions involving nitrones and alkynes--rapid tunable reactions for bioorthogonal labeling.
August 2014, Current opinion in chemical biology,
Kaitlyn D Margison, and Didier A Bilodeau, and Farnaz Mahmoudi, and John Paul Pezacki
Fluorogenic Bifunctional trans-Cyclooctenes as Efficient Tools for Investigating Click-to-Release Kinetics.
August 2020, Chemistry (Weinheim an der Bergstrasse, Germany),
Kaitlyn D Margison, and Didier A Bilodeau, and Farnaz Mahmoudi, and John Paul Pezacki
trans-Cyclooctenes as Halolactonization Catalysts.
October 2018, Angewandte Chemie (International ed. in English),
Kaitlyn D Margison, and Didier A Bilodeau, and Farnaz Mahmoudi, and John Paul Pezacki
Advances in the Synthesis of Bioorthogonal Reagents: s-Tetrazines, 1,2,4-Triazines, Cyclooctynes, Heterocycloheptynes, and trans-Cyclooctenes.
May 2024, Topics in current chemistry (Cham),
Kaitlyn D Margison, and Didier A Bilodeau, and Farnaz Mahmoudi, and John Paul Pezacki
Genetically encoded tetrazine amino acid directs rapid site-specific in vivo bioorthogonal ligation with trans-cyclooctenes.
February 2012, Journal of the American Chemical Society,
Kaitlyn D Margison, and Didier A Bilodeau, and Farnaz Mahmoudi, and John Paul Pezacki
Bioorthogonal labelling of living bacteria using unnatural amino acids containing nitrones and a nitrone derivative of vancomycin.
August 2015, Chemical communications (Cambridge, England),
Kaitlyn D Margison, and Didier A Bilodeau, and Farnaz Mahmoudi, and John Paul Pezacki
Nitrones as dipoles for rapid strain-promoted 1,3-dipolar cycloadditions with cyclooctynes.
February 2010, Chemical communications (Cambridge, England),
Copied contents to your clipboard!