ArticleJournal of the American Chemical Society2006
Exploring the limits of DNA size: naphtho-homologated DNA bases and pairs.
Article in Journal of the American Chemical Society, 2006. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
17 citing papers in PubMed.
- Heck-type C-glycosylations in the synthesis of artificial nucleotides and functional nucleic acids.RSC chemical biology · 2026Review
- The evolution of nucleoside analogue antivirals: A review for chemists and non-chemists. Part 1: Early structural modifications to the nucleoside scaffold.Antiviral research · 2018Review
- Artificial Base zT as Functional "Element" for Constructing Photoresponsive DNA Nanomolecules.Journal of the American Chemical Society · 2017Article
- Artificial genetic sets composed of size-expanded base pairs.Angewandte Chemie (International ed. in English) · 2013Review
- Structure-activity relationships for allosteric NMDA receptor inhibitors based on 2-naphthoic acid.Neuropharmacology · 2012Article
- One-pot etherification of purine nucleosides and pyrimidines.Organic letters · 2010Article
- Toward a designed genetic system with biochemical function: polymerase synthesis of single and multiple size-expanded DNA base pairs.Organic & biomolecular chemistry · 2010Article
- Fluorescent analogs of biomolecular building blocks: design, properties, and applications.Chemical reviews · 2010Review
- FRET enabled real time detection of RNA-small molecule binding.Journal of the American Chemical Society · 2009Article
- Structure and replication of yDNA: a novel genetic set widened by benzo-homologation.Chembiochem : a European journal of chemical biology · 2009Article
- Redesigning the architecture of the base pair: toward biochemical and biological function of new genetic sets.Chemistry & biology · 2009Review
- Mechanistic studies in the synthesis of a series of thieno-expanded xanthosine and guanosine nucleosides.Tetrahedron · 2008Article
- The development of versatile methods for palladium-catalyzed coupling reactions of aryl electrophiles through the use of P(t-Bu)3 and PCy3 as ligands.Accounts of chemical research · 2008Article
- A diazirine-based nucleoside analogue for efficient DNA interstrand photocross-linking.Journal of the American Chemical Society · 2008Article
- Hetero-expanded purine nucleosides. Design, synthesis and preliminary biological activity.Nucleic acids symposium series (2004) · 2008Article
- Furan Decorated Nucleoside Analogues as Fluorescent Probes: synthesis, photophysical evaluation and site-specific incorporation.Tetrahedron · 2007Article
- Synthesis and properties of size-expanded DNAs: toward designed, functional genetic systems.Accounts of chemical research · 2007Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
2 authors.
Funding
Abstract
A new design for DNA bases and base pairs is described in which the pyrimidine bases are widened by naphtho-homologation. Two naphtho-homologated deoxyribosides, dyyT (1) and dyyC (2), were synthesized and could be incorporated into oligonucleotides as suitably protected phosphoramidite derivatives. The deoxyribosides were found to be fluorescent, with emission maxima at 446 and 433 nm, respectively. Studies with single substitutions of 1 and 2 in the natural DNA context revealed exceptionally strong base stacking propensity for both. Sequences containing multiple substitutions of 1 and 2 paired opposite adenine and guanine were subsequently mixed and studied by several analytical methods. Data from UV mixing experiments, FRET measurements, fluorescence quenching experiments, and hybridizations on beads suggest that complementary "doublewide DNA" (yyDNA) strands may self-assemble into helical complexes with 1:1 stoichiometry. Data from thermal denaturation plots and CD spectra were less conclusive. Control experiments in one sequence context gave evidence that yyDNA helices, if formed, are preferentially antiparallel and are sequence selective. Hypothesized base pairing schemes are analogous to Watson-Crick pairing, but with glycosidic C1'-C1' distances widened by over 45%, to ca. 15.2 A. The possible self-assembly of the double-wide DNA helix establishes a new limit for the size of information-encoding, DNA-like molecules, and the fluorescence of yyDNA bases suggests uses as reporters in monomeric and oligomeric forms.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.