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Template-assisted photodimerization of N-unprotected uracil derivatives: selective formation of the cissyn photodimer

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Abstract

A UV light-induced photodimerization of 5-[(imidazol-1-yl)methyl]uracil using glutamate- and aspartate-derived cyclic dipeptides (2,5-diketopiperazines – DKPs) as templates was investigated. Dual salt bridge formation between imidazole side chains and carboxylic acids resulted in the preorganization of the uracil monomers and the preferential formation of the cissyn photodimer.

Graphical abstract: Template-assisted photodimerization of N-unprotected uracil derivatives: selective formation of the cis–syn photodimer

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Publication details

The article was received on 11 Jul 2017, accepted on 07 Aug 2017 and first published on 07 Aug 2017


Article type: Communication
DOI: 10.1039/C7CC05353C
Citation: Chem. Commun., 2017, Advance Article
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    Template-assisted photodimerization of N-unprotected uracil derivatives: selective formation of the cissyn photodimer

    N. M. Weckenmann, C. Maichle-Mössmer and B. J. Nachtsheim, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC05353C

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