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Synthesis and photophysical characterisation of new fluorescent triazole adenine analogues

Christopher P. Lawson ; Anke Dierckx (Institutionen för kemi- och bioteknik, Fysikalisk kemi) ; Francois-Alexandre Miannay (Institutionen för kemi- och bioteknik, Fysikalisk kemi) ; E. Wellner ; Marcus Wilhelmsson (Institutionen för kemi- och bioteknik, Fysikalisk kemi) ; Morten Grøtli
Organic & Biomolecular Chemistry (1477-0520). Vol. 12 (2014), 28, p. 5158-5167.
[Artikel, refereegranskad vetenskaplig]

Fluorescent nucleic acid base analogues are powerful probes of DNA structure. Here we describe the synthesis and photo-physical characterisation of a series of 2-(4-amino-5-(1H-1,2,3-triazol-4-yl)-7H-pyrrolo-[2,3-d] pyrimidin-7-yl) and 2-(4-amino-3-(1H-1,2,3-triazol-4-yl)-1H-pyrazolo[3,4-d] pyrimidin-1-yl) analogues via Sonogashira cross-coupling and [3 + 2]-cycloaddition reactions as the key steps in the synthesis. Compounds with a nitrogen atom in position 8 showed an approximately ten-fold increase in quantum yield and decreased Stokes shift compared to analogues with a carbon atom in position 8. Furthermore, the analogues containing nitrogen in the 8-position showed a more red-shifted and structured absorption as opposed to those which have a carbon incorporated in the same position. Compared to the previously characterised C8-triazole modified adenine, the emissive potential was significantly lower (tenfold or more) for this new family of triazoles-adenine compounds. However, three of the compounds have photophysical properties which will make them interesting to monitor inside DNA.

Nyckelord: DNA-BASE ANALOG, NUCLEOSIDE ANALOGS, PYRROLO-DC, CLICK CHEMISTRY, NUCLEIC-ACID, OLIGONUCLEOTIDES, PROBES, DUPLEX, HYBRIDIZATION, CONFORMATION



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Denna post skapades 2014-08-01. Senast ändrad 2015-08-25.
CPL Pubid: 200830

 

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Institutioner (Chalmers)

Institutionen för kemi och molekylärbiologi (GU)
Institutionen för kemi- och bioteknik, Fysikalisk kemi (2005-2014)

Ämnesområden

Livsvetenskaper
Nanovetenskap och nanoteknik
Biofysikalisk kemi
Spektroskopi
Organisk kemi

Chalmers infrastruktur