Photodimerization in pyrimidine-substituted dipeptides

Brian Lohse, P.S. Ramanujam, Søren Hvilsted, Rolf Henrik Berg

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Ten N-epsilon-glycylornithineamide derivatives have been synthesized containing various N-alpha-linked pyrimidine-1-ylacetyl groups which can undergo (2 pi + 2 pi) photodimerization on irradiation with UV light at 254 rim. The dimerization efficiency of the free and bound pyrimidine groups was compared in aqueous solution: it was dependent on the substitution of the pyrimidine ring. N-alpha,N-alpha'-bis-(uracil-1-ylacetyl)-(N-epsilon-glycylomithineamide) and N-alpha,N-alpha'-bis-(5-bromouracil-1-ylacetyl)-(N-epsilon-glycylomithineamide) were identified as possible candidates for optical data storage.
Original languageEnglish
JournalJournal of Peptide Science
Volume11
Issue number8
Pages (from-to)499-505
ISSN1075-2617
DOIs
Publication statusPublished - 2005

Keywords

  • Pyrimidine
  • Photodimerization
  • Cycloaddition
  • Dipeptide

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