Abstract
The efficiency of isotope exchange was compared when gaseous deuterium (solvent-free, solid-phase exchange) and deuterium water were employed as a deuterium source. It was established that exchange with deuterium water is preferable for producing labeled β-alanyl-L-histidine. When using the solid-phase method, the main part of the label is in histidine. The distribution of deuterium during isotope exchange with D2O is more uniform. In addition, the use of deuterium water makes it possible to reduce the amount of unlabeled isotopomer to 0.4% and receive a preparation with a yield of 40% (20 mg) and an average content of 3.6 deuterium atoms per carnosine molecule. It can be assumed that the high yield and greater incorporation of deuterium are associated with the pretreatment of the reaction mixture with gaseous deuterium.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Boldyrev, A.A., Biokhimiya, 2012, vol. 77, no. 4, pp. 403–418.
Bellia, F., Vecchio, G., Cuzzocrea, S., Calabrese, V., Rizzarelli, E., Mol. Aspects Med., 2011, vol. 32, no. 4–6, pp. 258–266. https://doi.org/10.1016/j.mam.2011.10.009
Boldyrev, A.A., Aldini, G., and Derave, W., Physiol. Rev., 2013, vol. 93, no. 4, pp. 1803–1845. https://doi.org/10.1152/physrev.00039.2012
Menon, K., Mousa, A., and de Courten, B., BMJ Open., 2018, vol. 8, no. 3. https://doi.org/10.1136/bmjopen-2017-020623
Artioli, G.G., Sale, C., and Jones, R.L., Eur. J. Sport Sci., 2019, vol. 19, no. 1, pp. 30–39. https://doi.org/10.1080/17461391.2018.1444096
Chik, J.K., Vande Graaf, J.L., and Schriemer, D.C., Anal. Chem., 2006, vol. 78, no. 1, pp. 207–214. https://doi.org/10.1021/ac050988l
Shevchenko, V.P., Nagaev, I.Yu., and Myasoedov, N.F., Mechennye tritiem lipofil’nye soedineniya (Tritiated Lipophilic Compounds), Moscow: Nauka, 2003.
Borisov, Yu.A. and Zolotarev, Yu.A., Zh. Fiz. Khim., 2002, vol. 76, no. 4, pp. 734–738.
Esaki, H., Ito, N., Sakai, S., Maegawa, T., Monguchi, Y., and Sajiki, H., Tetrahedron, 2006, vol. 62, no. 47, pp. 10954–10961. https://doi.org/10.1016/j.tet.2006.08.088
Lockley, W.J.S. and Hesk, D., J. Label. Compd. Radiopharm., 2010, vol. 53, no. 11–12, pp. 704–715. https://doi.org/10.1002/jlcr.1815
Maegawa, T., Fujiwara, Y., Inagaki, Y., Esaki, H., Monguchi, Y., and Sajiki, H., Angew. Chem. Int. Ed., 2008, vol. 47, no. 29, pp. 5394–5397. https://doi.org/10.1002/anie.200800941
Sajiki, H., Hattori, K., Aoki, F., Yasunaga, K., and Hirota, K., Synlett., 2002, no. 7, pp. 1149–1151. https://doi.org/10.1055/s-2002-32605
Sajiki, H., Aoki, F., Esaki, H., Maegawa, T., and Hirota, K., Org. Lett., 2004, vol. 6, no. 9, pp. 1485–1487. https://doi.org/10.1021/ol0496374
Funding
The work was supported by the theme no. 1021052806528-6-1.6.4;3.1.1;3.1.9;3.1.8;3.2.25 “Fundamental aspects of neuroplasticity in the framework of the model of translational neurology.”
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
The authors declare no conflict of interest.
Additional information
Translated from Radiokhimiya, No. 6, pp. 568–572, December, 2022 https://doi.org/10.31857/S0033831122060107
Rights and permissions
About this article
Cite this article
Shevchenko, V.P., Nagaev, I.Y., Myasoedov, N.F. et al. Production of Deuterium-Labeled β-Alanyl-L-histidine by Isotope Exchange. Radiochemistry 64, 735–739 (2022). https://doi.org/10.1134/S1066362222060108
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1066362222060108