What is Tetrazine ligation?
The tetrazine ligation is the reaction of a trans-cyclooctene and an s-tetrazine in an inverse-demand Diels Alder reaction followed by a retro-Diels Alder reaction to eliminate nitrogen gas.
What is the purpose of Bioorthogonal chemistry?
The broad range of bioorthogonal reactions with their associated reactants, key reagents, products and key feature(s) are highlighted here. Bioorthogonal chemistry enables probing biological systems through selective covalent bond formations that minimally disrupt the system(s) being studied.
What is the use of Tetrazine?
The tetrazine-alkene ligation has been used for imaging biomolecules like proteins (Devaraj, Weissleder, & Hilderbrand, 2008) and DNA (Rieder & Luedtke, 2014) in cells, imaging tumors in live animals (Devaraj, Thurber, Keliher, Marinelli, & Weissleder, 2012; Rossin et al., 2010), and for prodrug activation (Neumann.
How do you synthesize Tetrazine?
Direct Synthesis of Tetrazine Groups on Polymer Side Chains. In common synthetic approach, tetrazines are synthesized by a reaction of two nitrile groups in the presence of hydrazine and a catalyst, and a subsequent oxidation (Scheme 2).
What is Bioorthogonal labeling?
Genetic code expansion and bioorthogonal labeling of TARPs. Bioorthogonal labeling of proteins by replacing a single natural amino acid with a ncAA has emerged in the past years as an alternative strategy to target and visualize proteins in living mammalian cells with minimal to no perturbation32,33,38.
Who invented Bioorthogonal chemistry?
Bertozzi
Bertozzi coined the term in 2003 to describe reactions that do not interact or interfere with cells’ biology. As a UC Berkeley graduate student in the late 1980s and early 1990s, Bertozzi developed methods for the synthesis of bioactive glycan analogs.
What is Wittig reaction used for?
The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide called a Wittig reagent. Wittig reactions are most commonly used to convert aldehydes and ketones to alkenes.
What is Norbornyl system?
In organic chemistry, the term 2-norbornyl cation (or 2-bicyclo[2.2. 1]heptyl cation) describes one of the three carbocations formed from derivatives of norbornane.
What is the mechanism of Wittig reaction?
Mechanism of the Wittig Reaction. (2+2) Cycloaddition of the ylide to the carbonyl forms a four-membered cyclic intermediate, an oxaphosphetane. Preliminary posultated mechanisms lead first to a betaine as a zwitterionic intermediate, which would then close to the oxaphosphetane.
How is the Wittig reaction modified?
The Schlosser Modification of the Wittig Reaction allows the selective formation of E-alkenes through the use of excess lithium salts during the addition step of the ylide and subsequent deprotonation/protonation steps.
What is ethylidene group?
Ethylidene norbornene (ENB) is an organic compound that consists of an ethylene group attached to norbornene. It is a colorless liquid. The molecule consists of two sites of unsaturation, one of which participates in the copolymerization and the second of which (the ethylidene) undergoes vulcanization.
What is ethylidene dibromide?
CH3CH2Br.
What is Anchimeric assistance in organic chemistry?
Neighbouring group participation (NGP) (also known as anchimeric assistance) in organic chemistry has been defined by IUPAC as the interaction of a reaction centre with a lone pair of electrons in an atom or the electrons present in a sigma bond or pi bond contained within the parent molecule but not conjugated with …
What is tetrazine ligation?
The tetrazine ligation is an inverse electron demand Diels-Alder (IEDDA) reaction between s-tetrazines and alkenes/alkynes. It has gathered significant attention since its initial use for bioconjugation (Blackman, Royzen, & Fox, 2008).
Can tetrazines control the molecular aggregation and film morphology of hexathiophene?
The presence of tetrazines with hexyl- and 2-octyldodecyl substituted hexathiophene derivatives enabled control over the molecular aggregation and the film morphology ( 19D107717 ). In the field of energetic materials, new 1,2,4,5-tetrazines-based examples were synthesized, the performance of which were comparable to TATB and TNT, respectively.
How are tetrazines used in macromolecules?
Tetrazines were also used in the design of macromolecules. Indeed, functionalized O 6 -corona [3]arene [3]tetrazines were obtained by a condensation reaction between N -functionalized 3,6-dihydroxyphthalimides and 3,6-dichlorotetrazine in a one-pot manner.
Can tetrazine be used as a binding agent for imaging?
Imaging binding partners of a small molecule in live cells was also feasible with the tetrazine ligation reaction (Scheme 1). The first demonstration was labeling TCO-Taxol (Fig. 4a) with tetrazine-BODIPY FL (Fig. 4b) .