Synthetic incorporation of Nile Blue into DNA using 2′-deoxyriboside substitutes: Representative comparison of (R)- and (S)-aminopropanediol as an acyclic linker

• Daniel Lachmann,
• Sina Berndl,
• Otto S. Wolfbeis and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2010, 6, No. 13, doi:10.3762/bjoc.6.13

• Nile Blue chromophore was incorporated into oligonucleotides using “click” chemistry for the postsynthetic modification of oligonucleotides. These were synthesized using DNA building block 3 bearing an alkyne group and reacted with the azide 4. (R)-3-amino-1,2-propanediol was applied as the linker

• ]. Bioorthogonality is required for these ligation reactions in that both the functional group of the oligonucleotides and the functional group of the modifier should not be present in typical biomolecules and should react selectively with each other [11]. Over the last five years the Huisgen–Meldal–Sharpless “click

• visible spectrum) for use in “click” conjugation have been reported meanwhile [18]. The dye carrying the azide group was reacted with an alkyne group that was incorporated into the oligonucleotides as a nucleotide substituent. (S)-3-Amino-1,2-propanediol was used as an acyclic linker and substitute for