Synthesis of Anthropomorphic Molecules:  The NanoPutians

Chanteau, Stephanie H; Tour, James M.

doi:10.1021/jo0349227

Cited by 83 publications

(52 citation statements)

References 20 publications

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“…Finally, it should be noted that the structures of the tetrasubstituted spiroA C H T U N G T R E N N U N G [4,5]decatetraene-7-ones discussed in this contribution resemble humans, and the term anthropomorphic molecules, introduced by Tour et al for their NanoPutians, might apply for some of our molecules as well. [60,61] …”

Section: Resultsmentioning

confidence: 99%

Pd‐Catalyzed [2+2+1] Coupling of Alkynes and Arenes: Phenol Diazonium Salts as Mechanistic Trapdoors

Schmidt¹,

Berger²,

Kelling³

et al. 2011

Chemistry A European J

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Section: Resultsmentioning

confidence: 99%

Pd‐Catalyzed [2+2+1] Coupling of Alkynes and Arenes: Phenol Diazonium Salts as Mechanistic Trapdoors

Schmidt¹,

Berger²,

Kelling³

et al. 2011

Chemistry A European J

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“…They may be metallized (6,24) to create negative refractive index materials (25,26). They may be useful as building blocks for NanoPutians (27).…”

Section: Resultsmentioning

confidence: 99%

Defined DNA/nanoparticle conjugates

Ackerson

Sykes

Kornberg

2005

Proc. Natl. Acad. Sci. U.S.A.

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Glutathione monolayer-protected gold clusters were reacted by place exchange with 19-or 20-residue thiolated oligonucleotides. The resulting DNA͞nanoparticle conjugates could be separated on the basis of the number of bound oligonucleotides by gel electrophoresis and assembled with one another by DNA-DNA hybridization. This approach overcomes previous limitations of DNA͞ nanoparticle synthesis and yields conjugates that are precisely defined with respect to both gold and nucleic acid content.DNA-DNA hybridization ͉ monolayer-protected gold clusters ͉ nanostructure D NA-DNA hybridization has been exploited in the assembly of nanostructures (1-3), including nanomechanical (4, 5) and nanoelectronic (6) devices, molecular computation devices (7), biosensors, and DNA scaffolds (8). Many of these applications involve the use of DNA oligonucleotides tethered to gold nanoparticles. Additional oligonucleotides may be hybridized to these DNA͞nanoparticle conjugates, or nanoparticles may be hybridized with one another.Two types of DNA͞nanoparticle conjugates have been developed for these purposes. Both types entail the coupling of oligonucleotides through terminal thiol groups to colloidal gold particles. In one case, the oligonucleotides formed the entire monolayer coating the particles (3), whereas in the other case, the oligonucleotides were incorporated in a phosphine monolayer, and particles containing discrete numbers of oligonucleotides were separated by gel electrophoresis (2, 9). A minimal length of Ϸ50 residues was required, both for separation by electrophoresis and hybridization with complementary DNA sequences. These limitations of shorter oligonucleotides were attributed to interaction between the DNA and the gold surface (10, 11), with the DNA ''intrinsically bent'' (10) and wrapped around a colloidal particle (11), and with greatest affinity for C and G residues and least for A and T residues (12). Materials and MethodsOligonucleotides, synthesized by MWG Biotech, High Point, NC (www.mwgbiotech.com), were as follows: 20 residues, 5ЈSH-ACAACTTTCAACAGTCTAAC-3Ј; 19 residues, 5Ј-AGGC-CGCACCTAGGACGGT-3ЈSH; and 39 residues, complementary to 19 and 20 residues, TGTTGAAAGTTGTCAGATT-GTCCGGCGTGGATCCTGCCA. Glutathione monolayerprotected clusters (MPCs) were synthesized as described (13). Band 3, with a core of average mass 9 kDa, corresponding to 46 gold atoms, and diameter of 1.2 nm, was used. Oligonucleotides (10 l of 500 M) were reduced by treatment with 1 l of 50 mM Tris(2-caroxyethyl)phosphine (Sigma 646547) for 30 min at room temperature. Glutathione MPC (10 l of 1 mM) was added, followed by incubation for 1 h at 50°C.All gels were 15T͞5C acrylamide in TBE, run at a constant 100 V.A model of double-helical DNA with the sequence used here was generated with the use of NUCLEIC ACID BUILDER (14). The C6 5Ј-thiol and C3 3Ј-thiol linker regions were added to the models with PYMOL (15). Gold clusters were approximated as spheres. The DNA models were allowed to rotate about the axis of the thiol bond and attached to th...

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“…Diazotation of the commercially available 2,6-dibromo-4-nitroaniline (5), followed by reduction with ethanol, afforded 3,5-dinitrobenzene (6; 80%), 13 which was then submitted to the Suzuki-Miyaura coupling with the respective, commercially available aryl boronic acids. The coupling reaction was carried out in the presence of (AcO) 2 Pd as precatalyst and tri(o-tolyl)phosphine as ligand under standard conditions 14 to afford the 3,5-diaryl derivatives 7a 14 (69%) and 7b (80%).…”

Section: Catalyst Synthesismentioning

confidence: 99%