Department of Materials Science, University of Patras, 26504 Rio Patras, Greece, Theoretical and Physical Chemistry Institute, National Hellenic Research Foundation, 48 Vass. Constantinou Avenue, 116 35 Athens, Greece, Institut de Biologie Moleculaire et Cellulaire, UPR9021 CNRS, Immunologie et Chimie Therapeutiques, 67084 Strasbourg, France, and Dipartimento di Scienze Farmaceutiche, Universita di Trieste, Piazzale Europa 1, 34127 Trieste, Italy

Chemistry of Carbon Nanotubes

Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds

Arachidonic acid plays a central role in a biological control system where such oxygenated derivatives as prostaglandins, thromboxanes, and leukotrienes are mediators. The leukotrienes are formed by transformation of arachidonic acid into an unstable epoxide intermediate, leukotriene A4, which can be converted enzymatically by hydration to leukotriene B4, and by addition of glutathione to leukotriene C4. This last compound is metabolized to leukotrienes D4 and E4 by successive elimination of a gamma-glutamyl residue and glycine. Slow-reacting substance of anaphylaxis consists of leukotrienes C4, D4, and E4. The cysteinyl-containing leukotrienes are potent bronchoconstrictors, increase vascular permeability in postcapillary venules, and stimulate mucus secretion. Leukotriene B4 causes adhesion and chemotactic movement of leukocytes and stimulates aggregation, enzyme release, and generation of superoxide in neutrophils. Leukotrienes C4, D4, and E4, which are released from the lung tissue of asthmatic subjects exposed to specific allergens, seem to play a pathophysiological role in immediate hypersensitivity reactions. These leukotrienes, as well as leukotriene B4, have pro-inflammatory effects.

https://science.sciencemag.org/content/sci/220/4597/568.full.pdf

Leukotrienes: mediators of immediate hypersensitivity reactions and inflammation

Single-walled carbon nanotubes (SWNTs) are molecular wires that exhibit interesting structural, mechanical, electrical, and electromechanical properties. 1-3 A SWNT is unique among solidstate materials in that every atom is on the surface. Surface chemistry could therefore be critical to the physical properties of SWNTs and their applications. 3-10 SWNT sidewall functionalization is important to soluble nanotubes, 4-6 self-assembly on surfaces, and chemical sensors. 8-10 For these purposes, it is imperative to functionalize the sidewalls of SWNTs in noncovalent ways to preserve the sp 2 nanotube structure and thus their electronic characteristics. Immobilization of biomolecules on carbon nanotubes has been pursued in the past, motivated by the prospects of using nanotubes as new types of biosensor materials. 11-15 The electronic properties of nanotubes coupled with the specific recognition properties of the immobilized biosystems would indeed make for an ideal miniaturized sensor. A prerequisite for research in this area is the development of chemical methods to immobilize biological molecules onto carbon nanotubes in a reliable manner. Thus far, only limited work has been carried out with multiwalled carbon nanotubes (MWNTs). 11-15 Metallothionein proteins were trapped inside and placed onto the outer surfaces of open-ended MWNTs.11-14 Streptavidin was found to adsorb on MWNTs presumably via hydrophobic interactions between the nanotubes and hydrophobic domains of the proteins. 15 DNA molecules adsorbed on MWNTs via nonspecific interactions were also observed. 12-14

Noncovalent Sidewall Functionalization of Single-Walled Carbon Nanotubes for Protein Immobilization

4.2.8. Reductive Coupling 3109 5. Reaction of Aromatic Compounds 3110 5.1. Electrophilic Substitutions 3110 5.2. Radical Substitution 3111 5.3. Oxidative Coupling 3111 5.4. Photochemical Reactions 3111 6. Reaction of Carbonyl Compounds 3111 6.1. Nucleophilic Additions 3111 6.1.1. Allylation 3111 6.1.2. Propargylation 3120 6.1.3. Benzylation 3121 6.1.4. Arylation/Vinylation 3121 6.1.5. Alkynylation 3121 6.1.6. Alkylation 3121 6.1.7. Reformatsky-Type Reaction 3122 6.1.8. Direct Aldol Reaction 3122 6.1.9. Mukaiyama Aldol Reaction 3124 6.1.10. Hydrogen Cyanide Addition 3125 6.2. Pinacol Coupling 3126 6.3. Wittig Reactions 3126 7. Reaction of R,â-Unsaturated Carbonyl Compounds 3127

Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update

Especially in the field of enantioselective synthesis, vicinal diamines (1,2-diamines) 1 and compounds easily prepared from them-such as 1,2-bisimines, 1,2-diamides, or imidazolidin-2-ones-are widely used by organic chemists. Various strategies have been developed to produce these compounds selectively. Many natural products and medicinal agents also contain a 1,2-diamino unit.

The Chemistry of Vicinal Diamines.

Images of the assembly of surfactants and synthetic lipids on the surface of carbon nanotubes were obtained by transmission electron microscopy Above the critical micellar concentration, sodium dodecyl sulfate (SDS) forms supramolecular structures made of rolled-up half-cylinders on the nanotube surface Depending on the symmetry and the diameter of the carbon nanotube, we observed rings, helices, or double helices Similar self-assemblies were also obtained with several synthetic single-chain lipids designed for the immobilization of histidine-tagged proteins At the nanotube-water interface, permanent assemblies were produced from mixed micelles of SDS and different water-insoluble double-chain lipids after dialysis of the surfactant Such arrangements could be further exploited for the development of new biosensors and bioelectronic nanomaterials

https://science.sciencemag.org/content/sci/300/5620/775.full.pdf

Supramolecular Self-Assembly of Lipid Derivatives on Carbon Nanotubes

Two distinct proteins, streptavidin and HupR, bind and form regular helical arrays on the surface of multiwalled carbon nanotubes under appropriate conditions (see picture). The decoration of the outer surface of these nanostructures with biological macromolecules was investigated by electron microscopy.

Helical Crystallization of Proteins on Carbon Nanotubes: A First Step towards the Development of New Biosensors

Stereospecific total synthesis of a "slow reacting substance" of anaphylaxis, leukotriene C-1

A new and efficient procedure for ligand exchange on core−shell fluorescent nanocrystals is reported. The process involves the reaction of carbon disulfide with a ligand containing an amino group. The resulting dithiocarbamate is strongly bound to the surface of the quantum dots leading to a secure coating of the nanoparticle. The strategy was applied to the aqueous transfer of quantum dots.

Charles Mioskowski

Papers

The Chemistry of Vicinal Diamines.

Supramolecular Self-Assembly of Lipid Derivatives on Carbon Nanotubes

Helical Crystallization of Proteins on Carbon Nanotubes: A First Step towards the Development of New Biosensors

Stereospecific total synthesis of a "slow reacting substance" of anaphylaxis, leukotriene C-1

A versatile strategy for quantum dot ligand exchange.