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Photodimerization in pyrimidine‐substituted dipeptides
Author(s) -
Lohse Brian,
Ramanujam P. S.,
Hvilsted SØren,
Berg Rolf H.
Publication year - 2005
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.645
Subject(s) - pyrimidine , uracil , chemistry , alpha (finance) , ring (chemistry) , aqueous solution , stereochemistry , medicinal chemistry , dna , organic chemistry , biochemistry , mathematics , construct validity , statistics , psychometrics
Ten N ε ‐glycylornithineamide derivatives have been synthesized containing various N α ‐linked pyrimidine‐1‐ylacetyl groups which can undergo (2π + 2π) photodimerization on irradiation with UV light at 254 nm. 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 α , N α′ ‐bis‐(uracil‐1‐ylacetyl)‐( N ε ‐glycylornithineamide) and N α , N α′ ‐bis‐(5‐bromouracil‐1‐ylacetyl)‐( N ε ‐glycylornithineamide) were identified as possible candidates for optical data storage. Copyright © 2005 European Peptide Society and John Wiley & Sons, Ltd.