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Improved synthesis of [¹⁸F]FS-PTAD as a new tyrosine-specific prosthetic group for radiofluorination of biomolecules.
Appl Radiat Isot
October 2015
Department of Nuclear Medicine, University of Würzburg, Oberdürrbacher straße 6, D-97080 Würzburg, Germany. Electronic address:
A novel prosthetic group, 4-(p-([(18)F]fluorosulfonyl)phenyl)-1,2,4-triazoline-3,5-dione ([(18)F]FS-PTAD) for site-specific radiofluorination of tyrosine residue in small molecules is described. Coupling of [(18)F]FS-PTAD with L-tyrosine, N-acetyl-L-tyrosine methyl amide and phenol as model compounds were achieved in buffered aqueous solution at room temperature, resulting in the corresponding fluorinated tyrosine and phenol derivatives. The total synthesis time including radiosynthesis, HPLC purification and formulation was less than 60 min (n=15) with ≥98% radio chemical purity.
View Article and Find Full Text PDFSulfur mediated allylic C-H alkylation of tri- and disubstituted olefins.
Org Lett
November 2014
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, China.
A novel transition-metal-free, sulfur mediated allylic C-H alkylation reaction through a one-pot procedure involving an ene-like step between simple olefins and activated sulfoxides to generate allylic sulfonium intermediates, and a subsequent [2,3]-sigmatropic rearrangement step under basic conditions to give allylic C-H alkylation products, has been developed. This method is applicable to tri- and disubstituted olefin substrates in both inter- and intramolecular fashions.
View Article and Find Full Text PDFBimolecular hydrogen transfer in phenalene by a stepwise ene-like reaction mechanism.
Chem Commun (Camb)
June 2010
Department of Chemistry, Georgetown University, 37th & O Street, Washington, DC 20057-1227, USA.
For the hydrogen transfer of phenalene, a bimolecular ene-like mechanism is proposed, which is preferable over the hypothesized unimolecular rearrangement in the literature. Unique SOMO-SOMO pi-bonding of phenalenyl reduces the barriers of pericyclic reactions significantly. Pi-bonding between radicals is being recognized as a novel type of bonding interaction.
View Article and Find Full Text PDFTyrosine bioconjugation through aqueous ene-type reactions: a click-like reaction for tyrosine.
J Am Chem Soc
February 2010
The Skaggs Institute for Chemical Biology, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
A new and versatile class of cyclic diazodicarboxamides that reacts efficiently and selectively with phenols and the phenolic side chain of tyrosine through an ene-like reaction is reported. This mild aqueous tyrosine ligation reaction works over a broad pH range and expands the repertoire of aqueous chemistries available for small molecule, peptide, and protein modification. The tyrosine ligation reactions are shown to be compatible with the labeling of native enzymes and antibodies in a buffered aqueous solution.
View Article and Find Full Text PDFNovel ene-like cycloisomerization reaction of nitrile oxides with a tethered allyltrimethylsilyl group.
Angew Chem Int Ed Engl
May 2002
Department of Bioscience and Biotechnology, Faculty of Engineering, Okayama University, Tsushima, Okayama, 700-8530, Japan.
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