Longo, Beatrice published the artcileDesign, synthesis, conjugation and reactivity of novel trans,trans-1,5-cyclooctadiene-derived bioorthogonal linkers, Application In Synthesis of 1466420-02-9, the publication is Bioconjugate Chemistry (2020), 31(9), 2201-2210, database is CAplus and MEDLINE.
The tetrazine/trans cyclooctene (TCO) inverse-electron-demand Diels-Alder (IEDDA) reaction is the fastest bioorthogonal ”click” ligation process reported to date. In this context, TCO reagents have found widespread applications, however their availability and structural diversity is still somewhat limited, due to challenges connected with their synthesis and structural modification. To address this issue, a novel strategy for the conjugation of TCO derivatives to a biomol. was developed, which allows for the creation of greater structural diversity from a single precursor mol., i.e. trans,trans-1,5-cyclooctadiene [(E,E)-COD], whose preparation requires standard laboratory equipment and readily available reagents. This two-step strategy relies on the use of new bifunctional TCO-linkers (3aSR,9aSR,E)-I (R = 2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethyl, 2-[2-(2-(2-[(4-nitrophenoxycarbonyl)oxy]ethoxy)ethoxy)ethoxy]ethyl, (4-([(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl)phenyl)methyl, etc.) for IEDDA reactions, which can be synthesized via 1,3-dipolar cycloaddition of (E,E)-COD with different azido-spacers RN3 carrying an electrophilic function (NHS-ester, N-succinimidyl carbonate, p-nitrophenyl-carbonate, maleimide) in the ¦Ø-position. Following bioconjugation of these electrophilic linkers to the nucleophilic residue (cysteine or lysine) of a protein (step 1), the resulting TCO-decorated constructs can be subjected to a IEDDA reaction with tetrazines functionalized with fluorescent or near IR (NIR) tags (step 2). This strategy to label bovine serum albumin with the TCO-linker (3aSR,9aSR,E)-I (II, R = 14-[(2,5-dioxopyrrolidin-1-yl)oxy]-14-oxo-3,6,9,12-tetraoxatetradecan-1-yl) and to subsequently react it in a cell lysate with the fluorescein-isothiocyanate (FITC)-derived tetrazine II was successfully used. The same strategy was then used to label the bacterial wall of gram-pos. S. aureus showing the potential of these linkers for live-cell imaging. Finally, the impact of structural differences of the linkers upon the stability of the bioorthogonal constructs was determined The compounds for stability studies were prepared by conjugation of TCO-linkers (3aSR,9aSR,E)-I (R = (4-([(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl)phenyl)methyl, 2-[2-(2-(2-[(4-nitrophenoxycarbonyl)oxy]ethoxy)ethoxy)ethoxy]ethyl, II) to mAbs, such as Rituximab and Obinutuzumab, and subsequent labeling with a reactive Cy3-functionalized tetrazine.
Bioconjugate Chemistry published new progress about 1466420-02-9. 1466420-02-9 belongs to catalysis-chemistry, auxiliary class Copper-Free Click Chemistry,Tetrazine, name is (4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenyl)methanamine trifluoroacetic acid, and the molecular formula is C12H12F3N5O2, Application In Synthesis of 1466420-02-9.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia