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Review
. 2024 Jul;38(7):e5857.
doi: 10.1002/bmc.5857. Epub 2024 Mar 20.

Unique biomedical application of fluorescence derivatization based on palladium-catalyzed coupling reactions for HPLC analysis of pharmaceuticals and biomolecules

Mahmoud El-Maghrabey  1   2 , Naoya Kishikawa  1 , Naotaka Kuroda  1
Affiliations
Review

Unique biomedical application of fluorescence derivatization based on palladium-catalyzed coupling reactions for HPLC analysis of pharmaceuticals and biomolecules

Mahmoud El-Maghrabey et al. Biomed Chromatogr. 2024 Jul.

Abstract

Palladium-catalyzed coupling reactions are versatile and powerful tools for the construction of carbon-carbon bonds in organic synthesis. Although these reactions have favorable features that proceed selectively in mild reaction conditions using aqueous organic solvents, no attention has been given to their application in the field of biomedical analysis. Therefore, we focused on these reactions and evaluated the scope and limitations of their analytical performance. In this review, we describe the pros and cons and future trends of fluorescence derivatization of pharmaceuticals and biomolecules based on palladium-catalyzed coupling reactions such as Suzuki-Miyaura coupling, Mizoroki-Heck coupling, and Sonogashira coupling reactions for HPLC analysis.

Keywords: Mizoroki–Heck coupling; Sonogashira coupling; Suzuki–Miyaura coupling; fluorescence labeling; fluorogenic derivatization; palladium‐catalyzed coupling.

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References

REFERENCES

    1. Al‐Dirbashi, O., Qvarnstrom, J., Irgum, K., & Nakashima, K. (1998). Simple and sensitive high‐performance liquid chromatographic determination of methamphetamines in human urine as derivatives of 4‐(4,5‐diphenyl‐1H‐imidazol‐2‐yl) benzoyl chloride, a new fluorescence derivatization reagent. Journal of Chromatography B: Biomedical Sciences and Applications, 712(1–2), 105–112. https://doi.org/10.1016/S0378-4347(98)00128-5
    1. Ali, M. F. B., Uejo, Y., Kishikawa, N., Ohyama, K., & Kuroda, N. (2020). A selective and highly sensitive high performance liquid chromatography with fluorescence derivatization approach based on Sonogashira coupling reaction for determination of ethinyl estradiol in river water samples. Journal of Chromatography A, 1628, 461440. https://doi.org/10.1016/j.chroma.2020.461440
    1. Colbon, P., Ruan, J., Purdie, M., & Xiao, J. (2010). Direct acylation of aryl chlorides with aldehydes by palladium−pyrrolidine co‐catalysis. Organic Letters, 12(16), 3670–3673. https://doi.org/10.1021/ol101466g
    1. Cordovilla, C., Bartolomé, C., Martínez‐Ilarduya, J. M., & Espinet, P. (2015). The Stille reaction, 38 years later. ACS Catalysis, 5(5), 3040–3053. https://doi.org/10.1021/acscatal.5b00448
    1. Dachwitz, S., Duwe, D. H., Wang, Y. H., Gruß, H., Hannappel, Y., Hellweg, T., & Sewald, N. (2020). Suzuki‐Miyaura cross‐coupling of Bromotryptophan derivatives at ambient temperature. Chemistry—A European Journal, 26(69), 16357–16364. https://doi.org/10.1002/chem.202002454

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