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Research on Chemical Intermediates

, Volume 43, Issue 10, pp 5305–5320 | Cite as

Synthesis and photochemical reactivity of phthalimidoadamantane–tyrosine conjugates

  • Margareta Sohora
  • Nikolina Vidović
  • Kata Mlinarić-Majerski
  • Nikola BasarićEmail author
Article

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.

Graphical Abstract

Keywords

Phthalimide Tyrosine Peptides Photodecarboxylation Photoinduced electron transfer 

Notes

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.

Supplementary material

11164_2017_2927_MOESM1_ESM.pdf (1.1 mb)
Supplementary material 1 (PDF 1146 kb)

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Copyright information

© Springer Science+Business Media Dordrecht 2017

Authors and Affiliations

  1. 1.Department of Organic Chemistry and BiochemistryRuđer Bošković InstituteZagrebCroatia

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