Experimental measurement of aromatic stacking affinities in the context of duplex DNA

KM Guckian, BA Schweitzer, RXF Ren… - Journal of the …, 1996 - ACS Publications
Noncovalent interactions between aromatic molecules are widely believed to be important
contributing factors in the stabilization of organized structure in biological macromolecules …

[HTML][HTML] Selective and stable DNA base pairing without hydrogen bonds

TJ Matray, ET Kool - Journal of the American Chemical Society, 1998 - ncbi.nlm.nih.gov
Noncovalent interactions between aromatic nucleobases are the major stabilizing forces
which contribute to the structural integrity of duplex DNA and RNA. 1–3 However, base …

Hydrophobic, non-hydrogen-bonding bases and base pairs in DNA

BA Schweitzer, ET Kool - Journal of the american chemical …, 1995 - ACS Publications
We report the properties of hydrophobic isosteres of pyrimidines and purines in synthetic
DNA duplexes. Phenyl nucleosides 1 and 2 are nonpolar isosteres of the natural thymidine …

Factors contributing to aromatic stacking in water: evaluation in the context of DNA

KM Guckian, BA Schweitzer, RXF Ren… - Journal of the …, 2000 - ACS Publications
We report the use of thermodynamic measurements in a self-complementary DNA duplex (5
'-dXCGCGCG) 2, where X is an unpaired natural or nonnatural deoxynucleoside, to study …

DNA duplexes stabilized by modified monomer residues: synthesis and stability

JA Parkinson - Journal of the Chemical Society, Perkin Transactions …, 1998 - pubs.rsc.org
The synthesis of a series of 2′-deoxyuridine analogues modified at the 5-position and a
series of 2′-deoxypurines modified at the 8-position is described. Ultraviolet melting …

Measurement and theory of hydrogen bonding contribution to isosteric DNA base pairs

O Khakshoor, SE Wheeler, KN Houk… - Journal of the American …, 2012 - ACS Publications
We address the recent debate surrounding the ability of 2, 4-difluorotoluene (F), a low-
polarity mimic of thymine (T), to form a hydrogen-bonded complex with adenine in DNA. The …

A series of nonpolar thymidine analogues of increasing size: DNA base pairing and stacking properties

TW Kim, ET Kool - The Journal of Organic Chemistry, 2005 - ACS Publications
We describe the properties in DNA of a set of five nonpolar nucleoside mimics in which
shape is similar but size is increased gradually. The compounds vary in the size of their …

Tricyclo-DNA: a phosphodiester-backbone based DNA analog exhibiting strong complementary base-pairing properties

R Steffens, CJ Leumann - Journal of the American Chemical …, 1997 - ACS Publications
Due to their selective complementary base-association phenomena and their enhanced
resistance against enzymatic degradation, DNA analogs attract considerable attention as …

On the importance and origin of aromatic interactions in chemistry and biodisciplines

KE Riley, P Hobza - Accounts of chemical research, 2013 - ACS Publications
Aromatic systems contain both σ-and π-electrons, which in turn constitute σ-and π-molecular
orbitals (MOs). In discussing the properties of these systems, researchers typically refer to …

Remarkably stable parallel-stranded oligonucleotides containing 5-methylisocytosine and isoguanine

H Sugiyama, S Ikeda, I Saito - Journal of the American Chemical …, 1996 - ACS Publications
The polymorphic nature of double-stranded DNA is well established. 1 A common feature of
three major families of A-, B-, and Z-DNA duplexes is the antiparallel orientation of the …