Highly polar carbohydrates stack onto DNA duplexes via CH/π interactions.
Carbohydrate-nucleic acid contacts are known to be a fundamental part of some drug-DNA recognition processes. Most of these interactions occur through the minor groove of DNA, such as in the calicheamicin or anthracycline families, or through both minor and major groove binders such as in the pluramycins. Here, we demonstrate that carbohydrate-DNA interactions are also possible through sugar capping of a DNA double helix. Highly polar mono- and disaccharides are capable of CH/π stacking onto the terminal DNA base pair of a duplex as shown by NMR spectroscopy. The energetics of the carbohydrate-DNA interactions vary depending on the stereochemistry, polarity, and contact surface of the sugar involved and also on the terminal base pair. These results reveal carbohydrate-DNA base stacking as a potential recognition motif to be used in drug design, supramolecular chemistry, or biobased nanomaterials.
Department of Bioorganic Chemistry, Instituto de Investigaciones Químicas, CSIC-Universidad de Sevilla, Americo Vespucio, 49, 41092 Sevilla, Spain.
Ricardo
R
Lucas
Irene
I
Gómez-Pinto
Anna
A
Aviñó
Jose J
JJ
Reina
Ramón
R
Eritja
Carlos
C
González
Juan C
JC
Morales
D020029:Base Pairing; D001483:Base Sequence; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000737:chemistry*; D004247:DNA / Q000737:chemistry* / Q000235:genetics; D008958:Models, Molecular; D009838:Oligodeoxyribonucleotides / Q000737:chemistry / Q000235:genetics
D002241:Carbohydrates; D009838:Oligodeoxyribonucleotides; D004247:DNA