Journal
TETRAHEDRON
Volume 65, Issue 6, Pages 1171-1179Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.11.069
Keywords
Guanidine; Morpholinoamidine; Oligonucleotide; Nucleic acids analogues; Duplex; Triplex
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Funding
- Spanish Ministerio de Educacion y Ciencia [BQU-2001-3693-C02-01, CTQ-2004-8275-C02-01]
- Generalitat de Catalunya [2005SGR-693]
- University of Barcelona
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Morpholinoamidines were devised as new cationic units in oligonucleotides, by combining morpholino-nucleosides (to simplify the nomenclature, we Will use the term morpholino-nucleosides to refer to nucleoside analogues in which the ribose ring was transformed into a morpholine) with internucleoside guanidines. Here, methodology was developed to synthesize oligonucleotides containing morpholinoamidines formed by morpholino-uridine and 5'-amino-5'-deoxythymidine. Morpholinoamidine was produced by solid-phase reaction of Alloc-morpholinocarbothioamide with 5'-aminonucleoside resin and Mukaiyama's reagent activation. Two 14-mer oligonucleotides containing a single morpholinoamidine were synthesized and their affinity properties were investigated by forming DNA double and triple helices. Duplexes were slightly stabilized by a 3' unit, but were less stable if internally positioned. Notably, triplexes were significantly stabilized at pH 7.0 (C) 2008 Elsevier Ltd. All rights reserved.
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