476 research outputs found
Dataset for: The temperature stability and development of a broadband silver nanofluid for solar thermal applications
No full textDataset supports: Kimpton, H. J., Zhang, X., & Stulz, E. (2021). The Temperature Stability and Development of a Broadband Silver Nanofluid for Solar Thermal Applications. Energy Reports. </span
Data for Self‐assembled porphyrazine‐nucleoside on DNA templates
No full textSpectroscopic data of binding of compounds 1 and 2 to selected DNA sequences as described in the main text. Includes absorbance, fluorescence and CD data.
Data supports the paper:
Stulz, E., Berry, A., Ishutkina, M., Khelevina, O., Siligardi, G., & Hussain, R. (2018). Self‐assembled porphyrazine‐nucleoside on DNA templates: highly fluorescent chromophore arrays and sizing forensic tandem repeat sequences. European Journal of Organic Chemistry. DOI: 10.1002/ejoc.201800683</span
Dataset for A porphyrin-DNA chiroptical molecular ruler with base pair resolution
No full textDatasets for figures and analysis in: Stulz, E., Burns, J. R., & Wood, J. W. (2020). A porphyrin-DNA chiroptical molecular ruler with base pair resolution. Frontiers in Chemistry. </span
X-Ray structure and solvolytic activity towards phosphate diesters of a zirconium(IV) complex
No full textThe X-ray structure of the complex Zr-IV(acac)(2)(salicylideneaminoethanol) [Zr(acac)(2)(sae)] could be solved, and the reactivity of the complex towards phosphate diester solvolysis was investigated showing substantial rate acceleration over background in benzene-methanol solution (ca. 10(8)) and in aqueous medium (ca. 10(5))
Distamycin-NA: A DNA analog with an aromatic heterocyclic polyamide backbone. Part 1. Synthesis and structural analysis of monomers and dimers containing the nucleobase uracil
No full textThe synthesis of the monomeric building block 13 and its constitutional isomer 12 of a new type of DNA analog, distamycin-NA, is presented (Schemes I and 2). This building block consists of a uracil base attached to a thiophene core unit via a biaryl-like axis. Next to the biaryl-like axis on the thiophene chromophore, a carboxy and an amino substituent are located allowing for oligomerization pia peptide coupling. The proof of constitution and the conformational preferences about the biaryl-like axis were established by means of X-ray analyses of the corresponding nitro derivatives 10 and 11. Thus, the uracil bases are propeller-twisted relative to the thiophene core, and bidentate H-bonds occur between two uracil bases in the crystals. The two amino-acid building blocks 12 and 13 were coupled to give the dimers 15 and 16 using dicyclohexylcarbodiimide (DCC) in THF/LiCl and DMF. respectively. While the dimer 15 showed no atropisomerism on the NMR time scale at room temperature, its isomer 16 occurred as distinct diastereoisomers due to the hindered rotation around its biaryl-like axis. Variable-temperature H-1-NMR experiments allowed to determine a rotational barrier of 19 +/- 1 kcal/mol in 16. The experimental data were complemented by AM1 calculations
Porphyrin-modified DNA as construction material in supramolecular chemistry and nano-architectonics
No full textAn overview is given on the developments of using porphyrin-modified DNA for the construction of functional assemblies. Strategies for the synthesis and characterisation are presented alongside selected applications where the porphyrin modification has proven to be particularly useful, but also revealed its limitations. We also discuss implications on property and behaviour of the porphyrin-DNA, where similar issues could arise using other hydrophobic and bulky substituents on DNA
DNA architectonics: towards the next generation of bio-inspired materials
No full textThe use of DNA in nanobiotechnology has advanced to a stage at which almost any two or three dimensional architecture can be designed with high precision. The choice of the DNA sequences is essential for successful self-assembly, and opens new ways of making nanosized monomolecular assemblies with predictable structure and size. The inclusion of designer nucleoside analogues further adds functionality with addressable groups, which have an influence on the function of the DNA nano-objects. This article highlights the recent achievements in this emerging field and gives an outlook on future perspectives and application
Nanoarchitectonics with porphyrin functionalized DNA
No full textCONSPECTUS: DNA is well-known as bearer of the genetic code. Since its structure elucidation nearly seven decades ago by Watson, Crick, Wilkins, and Franklin, much has been learned about its detailed structure, function, and genetic coding. The development of automated solid-phase synthesis, and with it the availability of synthetic DNA with any desired sequence in lengths of up to hundreds of bases in the best case, has contributed much to the advancement of the field of DNA research. In addition, classic organic synthesis has allowed introduction of a very large number of modifications in the DNA in a sequence specific manner, which have initially been targeted at altering the biological function of DNA. However, in recent years DNA has become a very attractive scaffold in supramolecular chemistry, where DNA is taken out of its biological role and serves as both stick and glue molecule to assemble novel functional structures with nanometer precision. The attachment of functionalities to DNA has led to the creation of supramolecular systems with applications in light harvesting, energy and electron transfer, sensing, and catalysis. Functional DNA is clearly having a significant impact in the field of bioinspired nanosystems. Of particular interest is the use of porphyrins in supramolecular chemistry and bionanotechnology, because they are excellent functional groups due to their electronic properties that can be tailored through chemical modifications of the aromatic core or through insertion of almost any metal of the periodic table into the central cavity. The porphyrins can be attached either to the nucleobase, to the phosphate group, or to the ribose moiety. Additionally, noncovalent templating through Watson−Crick base pairing forms an alternative and attractive approach. With this, the combination of two seemingly simple molecules gives rise to a highly complex system with unprecedented possibilities for modulation of function, and with it applications, particularly when combined with other functional groups. Here, an overview is given on the developments of using porphyrin modified DNA for the construction of functional assemblies. Strategies for the synthesis and characterization are presented alongside selected applications where the porphyrin modification has proven to be particularly useful and superior to other modifiers but also has revealed its limitations. We also discuss implications on properties and behavior of the porphyrin−DNA, where similar issues could arise when using other hydrophobic and bulky substituents on DNA. This includes particularly problems regarding synthesis of the building blocks, DNA synthesis, yields, solubility, and intermolecular interactions
Synthesis and Spectroscopic Properties of Porphyrin-Substituted Uridine and Deoxyuridine
No full textA general synthetic route to porphyrin-substituted uridine and 2'-deoxyuridine using Sonogashira coupling with acetylene porphyrins is presented. Both diphenyl and tetraphenyl porphyrins, as free base or zinc metallated, can be attached to the nucleobase. Selective TBDMS protection of the deoxyribose does not affect the coupling reaction. The substituents on the porphyrins render the conjugates soluble either in organic solvents (carboxy esters) or in water (carboxylates). No electronic communication between the chromophore and the nucleobase occurs, as indicated by UV/Vis spectroscopy. In aqueous solution, the absorption of the porphyrins is substantially lower than in organic solvents
Bio-inspired functional DNA architectures
No full textDNA is well-known as bearer of the genetic code. Since its structure elucidation around seven decades ago by Watson, Crick, Wilkins and Franklin [1–3], much has been learnt about its detailed structure, function and genetic coding. In the field of DNA chemistry, solid-phase synthesis (SPS) of DNA certainly is one of the most influential developments of the last century [4–6] as it allows to synthesise DNA in any desired sequence and in lengths of up to hundreds of bases in the very best case. This has advanced the field of DNA research substantially. In addition, classic organic synthesis has allowed the introduction of a very large diversity of modifications in the DNA in a sequence-specific manner, which have initially been targeted at altering the biological function of DNA
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