Hybrid hexanucleotide duplex containing cyclonucleotides and deoxynucleotides: the d(TA) segment can adopt a high anti left-handed double-helical structure

It is known that oligonucleotides containing cyclonucleosides with a high anti (intermediate between anti and syn) glycosidic conformation adopt left-handed, single- and double-helical structures [Uesugi, S., Yano, J., Yano, E., & Ikehara, M. (1977) J. Am. Chem. Soc. 99, 2313-2323]. In order to...

Full description

Saved in:
Bibliographic Details
Published in:Biochemistry (Easton) 1988-01, Vol.27 (2), p.521-525
Main Authors: Uesugi, Seiichi, Lee, Bok Luel, Ikehara, Morio, Fujii, Satoshi, Tomita, Kenichi
Format: Article
Language:English
Subjects:
Biological and medical sciences
DNA
Fundamental and applied biological sciences. Psychology
Magnetic Resonance Spectroscopy - methods
Models, Molecular
Molecular biophysics
Nucleic Acid Conformation
Oligodeoxyribonucleotides
Structure in molecular biology
Structure-Activity Relationship
Tridimensional structure
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:It is known that oligonucleotides containing cyclonucleosides with a high anti (intermediate between anti and syn) glycosidic conformation adopt left-handed, single- and double-helical structures [Uesugi, S., Yano, J., Yano, E., & Ikehara, M. (1977) J. Am. Chem. Soc. 99, 2313-2323]. In order to see whether DNA can adopt the high anti left-handed double-helical structure or not, a self-complementary hexanucleotide containing 6,2'-O-cyclocytidine (C(o)), 8,2'-O-cycloguanosine (G(o)), thymidine, and deoxyadenosine, C(o)G(o)dTdAC(o)G(o), was synthesized. Imino proton NMR spectra and the results of nuclear Overhauser effect experiments strongly suggest that C(o)G(o)dTdAC(o)G(o) adopts a left-handed double-helical structure where the deoxynucleoside residues are involved in hydrogen bonding and take a high anti glycosidic conformation. A conformational model of the left-handed duplex was obtained by calculation with energy minimization. Thus it appears that DNA can form a high anti, left-handed double helix under some constrained conditions, which is quite different from that of Z-DNA.
ISSN:0006-2960
1520-4995
DOI:10.1021/bi00402a002