The synthesis of a promising brain imaging agent 4-[F-18]fluoro-4-deoxy-N-acetyl-1,3,6-tri-O-acetylglucosamine, 2, was successfully accomplished from commercially available N-acetyl glucosamine in 5 steps. The non-decay corrected radiochemical yield and purity were found to be 31% ± 4% (n = 3) and >98% respectively. The total reaction time for radio labelling step was 50 min.
References
[1]
Westermark, P. (1997) Classification of Amyloid Fibril Proteins and Their Precursors: An Ongoing Discussion. The Journal of Protein Folding Disorders, 4, 216-218. https://doi.org/10.3109/13506129709014387
[2]
Kisilevisky, R., Fraser, P.E. and Benson, M. (1997) AßT Amyloidogenesis: Unique, or Variation on a Systemic Theme. Critical Reviews in Biochemistry and Molecular Biology, 32, 361-404. https://doi.org/10.3109/10409239709082674
[3]
Lindhal, B., Eriksson, L. and Lindhal, U. (1995) Structure of Heparan Sulfate from Human Brain with Special Regards to Alazheimer’s Disease. BiochemicalJournal, 306, 177-184. https://doi.org/10.1042/bj3060177
[4]
Lindhal, B., Eriksson, L., Spillman, D., Caterson, B. and Lindhal, U. (1996) Selective Loss of Cerebral Keratan Sulfate in Alzheimer’s Disease. Journal of Biological Chemistry, 271, 16991-16994.
[5]
Lindhal, B. and Lindhal, U. (1997) Amyloid-Specific Heparin Sulfate in Human Liver and Spleen. Journal of Biological Chemistry, 272, 26091-26094. https://doi.org/10.1074/jbc.272.42.26091
[6]
Lindhal, B., Westling, C., Gimenez-Gallego, G., Lindhal, U. and Salmivirta, M. (1999) Common Binding Sites for β-Amyloid Fibrils and Fibroblast Growth Factor-2 in Heparan Sulfate from Human Cerebral Cortex. Journal of Biological Chemistry, 274, 30631-30635. https://doi.org/10.1074/jbc.274.43.30631
[7]
Fujiwara, T., Kubota, K., Sato, T., Matsuzawa, T., Tada, M., Iwata, R., Itoh, M., Hatazawa, J., Sato, K., Fakuta, H. and Ido, T. (1990) N-[18F]Fluoroacetyl Glucosamine: A Potential Agent for Cancer Diagnosis. Journal of Nuclear Medicine, 31, 1654-1658.
[8]
Martinez, M.E., Kiyoma, Y., Noriki, S., Inai, K., Mandap, K.S., Kobayashi, M., Mori, T., Tokunaga, Y., Tiwari, V.N., Okazawa, H., Fujibiashi, Y. and Ido, T. (2011) New Radiosynthesis of 2-Deoxy-2-[18F]Fluoroacetamido-D-Glucopyranose and Its Evaluation as Bacterial Infections Imaging Agent. Nuclear Medicine and Biology, 38, 807-817. https://doi.org/10.1016/j.nucmedbio.2011.02.006
[9]
Kisilevsky, R., Szarek, W.A., Ancsin, J., Bhat, S., Li, Z.J. and Marone, S. (2003) Novel Glycosaminoglycan Precursors as Anti-Amyloid Agents. Journal of Molecular Neuroscience, 20, 291-297. https://doi.org/10.1385/JMN:20:3:291
[10]
Inoue, Y., Onodera, K., Kitaoka, S. and Ochiai, H.H. (1957) An Acyl Migration in Acetohalogenoglucosamines. Journal of the American Chemical Society, 79, 4218-4222. https://doi.org/10.1021/ja01572a062
[11]
Galemmo, R.A. and Horton, D. (1983) Preparative Routes to Methyl 2-Acetamido-2,6-Dideoxy-α-Glucopyranoside. Carbohydrate Research, 119, 231-240. https://doi.org/10.1016/0008-6215(83)84058-0
[12]
Burger, P.J., Noshed, M.A. and Anderson, L. (1983) A Convenient Preparation of 2-Acetamido-2,6-Dideoxy-D-Glucose, Some of Its Alkyl Glycosides, and Allyl 2-Acetamido-2,6-Dideoxy-α-D-Galactopyranoside. Carbohydrate Research, 119, 221-230. https://doi.org/10.1016/0008-6215(83)84057-9
[13]
Chaplin, D., Crout, D.H.G., Borneman, S., Kutchinson D.W. and Khan, R. (1992) Conversion of 2-Acetamido-β-D-Glucopyranose into 2-Acetamido-Beta-D-Galactopyranos Using a Biotransformation to Generate a Selectively Deprotected Substrate for SN2 Inversion. Journal of the Chemical Society, Perkin Transactions, 1, 235-237. https://doi.org/10.1039/P19920000235
