Chromophore Arrays Constructed in the Major Groove of DNA Duplexes Using a Post‐Synthetic Strategy. Issue 4 (30th January 2019)

• Record Type: Journal Article
• Authors: Nakamura, Mitsunobu; Matsui, Yuki; Takada, Tadao; Yamana, Kazushige
• Is Part Of: ChemistrySelect. Volume 4:Issue 4(2019)
• Page Start: 1525
• Page End: 1529
• Publication Date: 2019-01-30
• Subjects: Aggregation -- Click chemistry -- Oligonucleotides -- Pyrene -- Tetraphenylethene; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201803464
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: The construction of zipper‐like chromophore‐arrays in the major groove of duplex DNA remains a challenge because only a few chromophores for this application have been discovered. To address the challenge, dual‐chromophore labeled DNAs having a self‐complementary sequence were prepared using a solid‐phase, post‐synthetic, copper‐catalyzed, alkyne‐azide cycloaddition. The resulting chromophore‐arrays on the labeled DNA duplexes were characterized. The dual‐tetraphenylethene (TPE) or dual‐pyrene (Py) labeled DNA formed self‐complementary B‐form duplexes and resulted in the construction of chromophore‐arrays in the major groove. The TPE‐arrays, in which TPEs were arranged in a zipper‐like fashion, slightly destabilized the duplex because of their bulkiness and exhibited aggregation‐induced‐emission. The Py‐arrays, in which Pys were not arranged in a zipper‐like fashion, had no effect on duplex stability and exhibited weak excimer emission because Py was sufficiently small for free rotation in the major groove. Abstract : The construction of zipper‐like chromophore‐arrays in the major groove of duplex DNA remains a challenge because only a few chromophores have been found suitable. We report dual‐chromophore‐labeled DNAs prepared by a post‐synthetic copper‐catalyzed alkyne‐azide cycloaddition. The resulting major groove chromophore‐arrays were characterized.