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Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity.
A bioorthogonal reaction that proceeds with unusually fast reaction rates without need for catalysis: the cycloaddition of s-tetrazine and trans-cyclooctene derivatives, which enables protein modification at low concentration.
Genetic Encoding of Bicyclononynes and trans-Cyclooctenes for Site-Specific Protein Labeling in Vitro and in Live Mammalian Cells via Rapid Fluorogenic Diels–Alder Reactions
A fluorogenic reaction between bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN) and tetrazines that is 3–7 orders of magnitude faster than many bioorthogonal reactions is reported.
Development and Evaluation of 18F-TTCO-Cys40-Exendin-4: A PET Probe for Imaging Transplanted Islets
18F-TTCO-Cys40-exendin-4 demonstrated its great potential for transplanted islet imaging: the liver uptake value derived from small-animal PET images correlated well with the transplanted β-cell mass determined by immunostaining and the localizations of radioactive signal indeed corresponded to the distribution of islet grafts in the liver of is let-transplanted mice.
Diels-Alder cycloaddition for fluorophore targeting to specific proteins inside living cells.
By incorporating the Diels-Alder cycloaddition, this work has broadened the panel of fluorophores that can be targeted by lipoic acid ligase and achieved specific labeling of cytoskeletal proteins with green and red fluorophore conjugate.
Design and synthesis of highly reactive dienophiles for the tetrazine-trans-cyclooctene ligation.
Computation was used to design a trans-cyclooctene derivative that displays enhanced reactivity in the tetrazine-trans-cycloctene ligation, in which the eight-membered ring is forced to adopt a highly strained 'half-chair' conformation.
Genetically encoded tetrazine amino acid directs rapid site-specific in vivo bioorthogonal ligation with trans-cyclooctenes.
A tetrazine-containing amino acid, 1, is developed that can be ligated to a conformationally strained trans-cyclooctene in vitro and in vivo with reaction rates significantly faster than most commonly used labeling methods.
trans-Cyclooctene--a stable, voracious dienophile for bioorthogonal labeling.
  • R. Selvaraj, J. Fox
  • Biology, Chemistry
    Current opinion in chemical biology
  • 1 October 2013
Chiral crown conformation of Rh(2)(S-PTTL)(4): enantioselective cyclopropanation with alpha-alkyl-alpha-diazoesters.
Herein, we provide crystallographic and computational evidence that Hashimoto's Rh(2)(S-PTTL)(4) catalyst adopts a "chiral crown" conformation with a reactive chiral face and an unreactive achiral
A photochemical synthesis of functionalized trans-cyclooctenes driven by metal complexation.
The method provides access to a range of usefully functionalized derivatives of trans-cyclooctene, including a derivative of 5-aza-trans-cyclOOctene that underwent transannular cyclization upon treatment with bromine.
Computational studies of nucleophilic substitution at carbonyl carbon: the S(N)2 mechanism versus the tetrahedral intermediate in organic synthesis.
Results corroborate earlier suggestions that the methanolysis of acetyl chloride does not proceed through the generally assumed addition-elimination pathway with a discrete tetrahedral intermediate but is consistent with ionization of Cl(-).