Direct 11 CN-Labeling of Unprotected Peptides via Palladium-Mediated Sequential Cross-Coupling Reactions

Journal of the American Chemical Society
Wenjun ZhaoJacob M Hooker

Abstract

A practical procedure for 11CN-labeling of unprotected peptides has been developed. The method was shown to be highly chemoselective for cysteine over other potentially nucleophilic residues, and the radiolabeled products were synthesized and purified in less than 15 min. Appropriate for biomedical applications, the method could be used on an extremely small scale (20 nmol) with a high radiochemical yield. The success of the protocol stems from the use of a Pd-reagent based on a dihaloarene, which enables direct "nucleophile-nucleophile" coupling of the peptide and [11C]cyanide by temporal separation of nucleophile addition.

References

Jan 1, 1996·Annual Review of Cell and Developmental Biology·E Ruoslahti
Sep 5, 2002·Nature Reviews. Cancer·Sanjiv Sam Gambhir
May 27, 2006·Science·Ralph Weissleder
Aug 5, 2006·Angewandte Chemie·Ralf SchirrmacherKlaus Jurkschat
Apr 23, 2008·Chemical Reviews·Simon M AmetameyPius August Schubiger
Nov 7, 2008·Angewandte Chemie·Philip W MillerAntony D Gee
Feb 16, 2010·Biochimica Et Biophysica Acta·Vladimir Tolmachev, Sharon Stone-Elander
Mar 27, 2010·Chemistry & Biology·Emmanuel BasléMathieu Pucheault
Nov 17, 2012·Journal of the American Chemical Society·Phillip J MilnerStephen L Buchwald
Dec 4, 2012·Chemical Reviews·Cathy S CutlerSilvia S Jurisson
Aug 16, 2013·Journal of Peptide Science : an Official Publication of the European Peptide Society·Masayuki HanyuToshimitsu Fukumura
Oct 5, 2013·Nuclear Medicine and Biology·Ying LiDavid M Perrin
Jan 11, 2014·Journal of Labelled Compounds & Radiopharmaceuticals·Peter LavermanOtto C Boerman
Sep 10, 2014·Chemical Society Reviews·Yu Heng LauDavid R Spring
Dec 2, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·David Brasse, Aline Nonat
Dec 11, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Susan Richter, Frank Wuest
Jan 8, 2015·Journal of the American Chemical Society·Hong Geun LeeJacob M Hooker
Feb 5, 2015·Chemical Communications : Chem Comm·Jenilee D WayFrank Wuest
Feb 24, 2015·Chemical Reviews·Omar Boutureira, Gonçalo J L Bernardes
Jun 19, 2015·Bioconjugate Chemistry·Orit JacobsonXiaoyuan Chen
Oct 30, 2015·Nature·Ekaterina V VinogradovaStephen L Buchwald
Dec 22, 2015·Seminars in Nuclear Medicine·Michael S PlaczekJacob M Hooker
Jan 23, 2016·Chemical Society Reviews·Qi-Ying HuRoberto Adamo
Apr 5, 2016·Chemical Communications : Chem Comm·Aristeidis ChiotellisThomas L Mindt
Nov 8, 2016·Biophysical Reports·Jiyun ShiShuang Liu
Dec 17, 2016·Angewandte Chemie·James W B FyfeAllan J B Watson

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Citations

Jan 10, 2018·Angewandte Chemie·Haifeng YangAndrew J Hoover
Jun 5, 2018·Angewandte Chemie·Antonio Del VecchioDavide Audisio
Feb 8, 2018·Molecular Imaging and Biology : MIB : the Official Publication of the Academy of Molecular Imaging·Aleksandra PekošakAlbert D Windhorst
Sep 7, 2018·Angewandte Chemie·Jens Rickmeier, Tobias Ritter
Nov 7, 2018·Angewandte Chemie·Chi ZhangBradley L Pentelute
Feb 16, 2019·Chemical Communications : Chem Comm·Kengo HanayaZachary T Ball
Aug 15, 2017·Angewandte Chemie·Cecilia BottecchiaTimothy Noël
Jul 13, 2018·Chemical Science·Philippe BisseretNicolas Blanchard
Jan 22, 2021·Organic Letters·Jacob RodriguezStephen L Buchwald
Mar 5, 2021·Analytical Chemistry·Lili CuiLianyou Zheng
Jun 2, 2021·Journal of the American Chemical Society·Mary A WaddingtonAlexander M Spokoyny
Jul 21, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Morgan CormierPhilippe Hermange
Sep 21, 2018·Organic Letters·Emmanuelle DubostThomas Cailly
May 5, 2020·Journal of the American Chemical Society·Heemal H DhanjeeBradley L Pentelute
Jun 30, 2019·Organic Letters·Manuel KöckingerC Oliver Kappe
Feb 7, 2018·Journal of the American Chemical Society·Koji KubotaStephen L Buchwald
Jan 6, 2018·Journal of the American Chemical Society·Stefan VerhoogVéronique Gouverneur
Oct 24, 2017·Journal of the American Chemical Society·Victoria DimakosMark S Taylor
Jul 17, 2019·Journal of the American Chemical Society·Anne K RavnTroels Skrydstrup
Jan 9, 2020·Journal of the American Chemical Society·Choon Wee KeeVéronique Gouverneur

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