Base-pairing mediated non-covalent polymers

Abstract

The naturally occurring nucleic acid bases (nucleobases) adenine, thymine (uracil), guanine, and cytosine are widely appreciated for their ability to stabilize canonical Watson-Crick base-pairing motifs, as well as a number of other well-characterized arrangements, such as Hoogsteen and wobble heterodimers, and a variety of homodimers. In this tutorial review, the use of these kinds of interactions to form synthetic polymeric and oligomeric ensembles is summarized. Particular emphasis will be placed on synthetic analogues of guanine that stabilize the formation of well-defined higher order aggregates, as well as de novo polymeric systems whose properties are modulated by the presence of nucleobase derivatives incorporated within or attached to the chain-defining backbone. In both cases, nucleobase-nucleobase interactions serve to underlie the chemistry, establish the structural morphology, and enable the development of bioinspired, environmentally responsive materials.

DNA‐Inspired Hierarchical Polymer Design: Electrostatics and Hydrogen Bonding in Concert

“…Figure 2 shows the chemical structure for DNA and three common hydrogen bonding configurations: Watson‐Crick base pairing between adenine/thymine and guanine/cytosine and also a Hoogsteen base pair between uracil and adenine 23. While the hydrogen bonding creates specificity and a method to copy the genetic code in DNA, hydrogen bonding itself does not greatly add to the stabilization of the DNA double helix 1, 24, 25.…”

Tuning the hydrogen-bonding strength in 2,6-bis(cycloalkylcarbonylamino)pyridine assemblies by variable flexibility. Association constants measured by hydrogen-bonded vs. non-hydrogen-bonded protons

“…Triple hydrogen-bonded associates are met in many structures as in DNA [14,15], amides [16,17], artificial sensors [18][19][20][21][22], materials [23], non-covalent polymers [4,[24][25][26][27][28] and in recently observed associates of orotic acid [29,30]. Triple hydrogen-bonded assemblies carrying 2,6-diaminopyridine DAD-hydrogen bonding moiety were studied by some groups with the use of various methods [4,6,[31][32][33][34][35][36][37][38][39][40][41][42][43][44][45][46][47] and also by us [48,49]. We noticed that the use of NH and CH proton shifts as probes in Previously [48] we confirmed results from other group [50] reporting that the 2,6-bis(acylamino)pyridine do not dimerize.…”

“…The non-covalent assemblies of small molecules stabilized by weak and directional interactions such as hydrogen bonds [1][2][3] are under regular studies, so the number of publications on supramolecular chemistry is increasing fast [4]. Various methods have been developed for understanding the stability of associates based on molecular properties [5].…”

Nanorod-Shaped Basic Al2O3 Catalyzed N,N-Diformylation of Bisuracil Derivatives: A Greener “NOSE” Approach

“…One of the key motifs present in the biopolymer RNA [23–26] is uracil, a nucleobase of the pyrimidine family which participates in various functions in our life processes [27]. Uracil derivatives also have several potent medicinal properties such as bronchodilators and anticancer [28, 29], antiallergic [30, 31], antiviral [32, 33], antihypertensive, and adenosine receptor antagonists [34, 35].…”