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Synthesis and photochemical reactivity of phthalimidoadamantane–tyrosine conjugates

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Abstract

Dipeptide 3, tetrapeptide 4 and pentapeptide 5, containing adamantylphthalimide and tyrosine, were synthesized and their photochemical reactivity investigated. Upon excitation to the triplet excited state, 3 does not give any photoproduct, although the photoinduced electron transfer (PET) should take place based on the thermodynamic properties. Tetrapeptide 4 and pentapeptide 5 are photochemically reactive, undergoing decomposition upon excitation. The lack of anticipated photodecarboxylation reactivity is explained by PET between the tyrosine and the phthalimide. However, deprotonation of the phenoxyl radical-cation giving phenoxyl radicals or back electron transfer giving starting material are probably faster than intrastrand single electron transfer which would lead to carboxyl radical and decarboxylation. The results indicate the importance of fine-tuning the molecular structure to attain the desired photoreactivity by the right choice of the reactants redox potential, as well as their acid/base properties.

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Acknowledgements

These materials are based on work financed by the Croatian Science Foundation (HrZZ grant no. IP-2014-09-6312). The authors declare that they have no conflict of interest.

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Authors and Affiliations

  1. Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000, Zagreb, Croatia

    Margareta Sohora, Nikolina Vidović, Kata Mlinarić-Majerski & Nikola Basarić

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  1. Margareta Sohora
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  2. Nikolina Vidović
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  3. Kata Mlinarić-Majerski
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  4. Nikola Basarić
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Correspondence to Nikola Basarić.

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Sohora, M., Vidović, N., Mlinarić-Majerski, K. et al. Synthesis and photochemical reactivity of phthalimidoadamantane–tyrosine conjugates. Res Chem Intermed 43, 5305–5320 (2017). https://doi.org/10.1007/s11164-017-2927-2

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