TY - JOUR
T1 - Crystal structure of homo-DNA and nature's choice of pentose over hexose in the genetic system
AU - Egli, Martin
AU - Pallan, Pradeep S.
AU - Pattanayek, Rekha
AU - Wilds, Christopher J.
AU - Lubini, Paolo
AU - Minasov, George
AU - Dobler, Max
AU - Leumann, Christian J.
AU - Eschenmoser, Albert
PY - 2006/8/23
Y1 - 2006/8/23
N2 - An experimental rationalization of the structure type encountered in DNA and RNA by systematically investigating the chemical and physical properties of alternative nucleic acids has identified systems with a variety of sugar-phosphate backbones that are capable of Watson-Crick base pairing and in some cases cross-pairing with the natural nucleic acids. The earliest among the model systems tested to date, (4′ → 6′)-linked oligo(2′,3′-dideoxy-β-D-glucopyranosyl)nucleotides or homo-DNA, shows stable self-pairing, but the pairing rules for the four natural bases are not the same as those in DNA. However, a complete interpretation and understanding of the properties of the hexapyranosyl (4′ → 6′) family of nucleic acids has been impeded until now by the lack of detailed 30-structural data. We have determined the crystal structure of a homo-DNA octamer. It reveals a weakly twisted right-handed duplex with a strong inclination between the hexose-phosphate backbones and base-pair axes, and highly irregular values for helical rise and twist at individual base steps. The structure allows a rationalization of the inability of allo-, altro-, and glucopyranosyl-based oligonucleotides to form stable pairing systems.
AB - An experimental rationalization of the structure type encountered in DNA and RNA by systematically investigating the chemical and physical properties of alternative nucleic acids has identified systems with a variety of sugar-phosphate backbones that are capable of Watson-Crick base pairing and in some cases cross-pairing with the natural nucleic acids. The earliest among the model systems tested to date, (4′ → 6′)-linked oligo(2′,3′-dideoxy-β-D-glucopyranosyl)nucleotides or homo-DNA, shows stable self-pairing, but the pairing rules for the four natural bases are not the same as those in DNA. However, a complete interpretation and understanding of the properties of the hexapyranosyl (4′ → 6′) family of nucleic acids has been impeded until now by the lack of detailed 30-structural data. We have determined the crystal structure of a homo-DNA octamer. It reveals a weakly twisted right-handed duplex with a strong inclination between the hexose-phosphate backbones and base-pair axes, and highly irregular values for helical rise and twist at individual base steps. The structure allows a rationalization of the inability of allo-, altro-, and glucopyranosyl-based oligonucleotides to form stable pairing systems.
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U2 - 10.1021/ja062548x
DO - 10.1021/ja062548x
M3 - Article
C2 - 16910680
AN - SCOPUS:33747792737
VL - 128
SP - 10847
EP - 10856
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 33
ER -