Journal of Radiopharmaceuticals and Molecular Probes (대한방사성의약품학회지)

Korean Society of Radiopharmaceuticals and Molecular Probes (대한방사성의약품학회)
권호 표지
DOI QR코드

DOI QR Code

A novel 11CN-labeling approach to aryl compounds and peptides using palladium complex

  • Kim, Hee-Kwon (Department of Nuclear Medicine, Molecular Imaging & Therapeutic Medicine Research Center, Cyclotron Research Center, Biomedical Research Institute, Chonbuk National University Medical School and Hospital)
  • Received : 2017.12.11
  • Accepted : 2017.12.26
  • Published : 2017.12.30
Download PDF
⟨ Previous Next ⟩

Abstract

Since the nitrile group is commonly found in natural products and bioactive molecules, many scientists' interest has been focused on the usage of nitrile group. Novel reactions for $^{11}C-labelling$ using nitrile group have been developed, and novel preparation protocols of biomolecules labeled with $^{11}C$ have been studied. In this highlight review, recent researches for the novel labeling reactions using nitrile group are illustrated.

Keywords

References

  1. Miller PW, Long NJ, Vilar R, Gee AD. Synthesis of $^{11}C$, $^{18}F$, $^{15}O$, and $^{13}N$ radiolabels for positron emission tomography . Angew Chem Int Ed Engl 2008;47:8998-9033. https://doi.org/10.1002/anie.200800222
  2. Iwata R, Ido T, Takahashi T, Nakanishi H, Iida S. Optimization of [$^{11}C$]HCN production and no-carrier-added [1-$^{11}C$]amino acid synthesis. Int J Rad Appl Instrum A 1987;38:97-102. https://doi.org/10.1016/0883-2889(87)90003-7
  3. Somawardhana CW, Sajjad M, Lambrecht RM. Novel solidstate support for rapid synthesis of radiopharmaceuticals labelled with [$^{11}C$]-cyanide. J Chem Soc Chem Comm 1990;0:370-371.
  4. Gillings NM, Gee AD. Synthesis of [4-$^{11}C$]amino acids via ring-opening of aziridine-2-carboxylates. J Labelled Compd Radiopharm 2014;44:909-920.
  5. Andersson Y, Langstrom B. Transition metal-mediated reactions using [$^{11}C$]cyanide in synthesis of $^{11}C$-labelled aromatic compounds. J Chem Soc Perkin Trans. 1 1994;0:1395-1400.
  6. Andersson Y, Bergstrom M, Langstrom B. Synthesis of $^{11}C$-labelled benzamide compounds as potential tracers for poly(ADP-ribose) synthetase. Appl Radiat Isot 1994;45:707-714 https://doi.org/10.1016/0969-8043(94)90251-8
  7. Anbarasan P, Schareina T, Beller M. Recent developments and perspectives in palladium-catalyzed cyanation of aryl halides: synthesis of benzonitriles. Chem Soc Rev 2011;40:5049-5067. https://doi.org/10.1039/c1cs15004a
  8. Lee HG, Milner PJ, Placzek MS, Buchwald SL, Hooker JM. Virtually instantaneous, room-temperature $^{11}CN$-cyanation using biaryl phosphine Pd(0) complexes. J Am Chem Soc 2015;137:648-651. https://doi.org/10.1021/ja512115s
  9. Senecal TD, Shu W, Buchwald SL. A general, practical palladium-catalyzed cyanation of (hetero)aryl chlorides and bromides. Angew Chem Int Ed Engl 2013;52:10035-10039. https://doi.org/10.1002/anie.201304188
  10. Zhao W, Lee HG, Buchwald SL, Hooker JM. Direct $^{11}CN$-Labeling of Unprotected Peptides via Palladium-Mediated Sequential Cross-Coupling Reactions. J Am Chem Soc 2017;139:7152-7155. https://doi.org/10.1021/jacs.7b02761