123155-06-6Relevant articles and documents
Per(3-deoxy)-γ-cyclomannin: A non-glucose cyclooligosaccharide featuring inclusion properties
Yang, Cheng,Yuan, De-Qi,Nogami, Yasuyoshi,Fujita, Kahee
, p. 4641 - 4644 (2003)
Per(3-deoxy)-γ-cyclomannin has been efficiently synthesized by a three-step procedure starting from natural γ-cyclodextrin, and proved to be capable of binding naphthalenesulfonate in aqueous solution and solubilizing C60 in water. For the first time it was spectrally evidenced that a non-glucose cyclooligosaccharide did form inclusion complexes with conventional organic guest molecules.
A family of single-isomer, sulfated γ-cyclodextrin chiral resolving agents for capillary electrophoresis. 1. Octakis(2,3-diacetyl-6-sulfato)-γ- cyclodextrin
Zhu, Wenhong,Vigh, Gyula
, p. 310 - 317 (2000)
The first member of the single-isomer, sulfated γ-cyclodextrin family, the sodium salt of octakis(2,3-diacetyl-6-sulfato)-γ-cyclodextrin (ODAS- γCD) has been synthesized, analytically characterized, and used to separate, by capillary electrophoresis, a variety of neutral, acidic, basic, and amphoteric enantiomers in low pH background electrolytes. The anionic effective mobilities of the neutral and anionic analytes were found to increase with the concentration of ODAS-γCD. For weakly binding cationic analytes, the effective mobilities went from cationic high values, through zero, to increasingly larger anionic values as the concentration of ODAS-γCD was increased. For the strongly complexing cationic analytes, the effective mobilities became anionic even at very low ODAS-γCD concentrations and became smaller as the ionic strength of the background electrolyte increased with the increasing ODAS-γCD concentration. Separation selectivity followed the predictions of the charged resolving agent migration model: for neutral analytes it decreased as the concentration of ODAS-γCD was increased. For cationic analytes, selectivities were found to increase as the cationic effective mobilities approached zero, then decreased as the concentration of ODAS-γCD was increased further. The extent of peak resolution that could be realized with ODAS-γCD strongly depended on the magnitude of separation selectivity and the normalized electroosmotic flow mobility. ODAS-γCD proved to be a broadly applicable chiral resolving agent.
New cyclodextrin dimers and trimers capable of forming supramolecular adducts with shape-specific ligands
Aime, Silvio,Gianolio, Eliana,Arena, Francesca,Barge, Alessandro,Martina, Katia,Heropoulos, George,Cravotto, Giancarlo
scheme or table, p. 370 - 379 (2009/03/11)
Bridged cyclodextrin dimers and trimers, in which respectively two and three hydrophobic cavities lie in close proximity, display much higher binding affinities and molecular selectivities than do parent cyclodextrins (CDs). By joining βCD units with links inserted at different positions (2-2′, 3-2′, 6-2′ or 6-2′-6″) and interposing spacers of different lengths and shapes, multicavity structures can be synthesized that are precisely tailored to fit specific guest molecules. This enzyme-mimicking strategy can also be used to generate stable supramolecular adducts. A series of CD dimers and trimers was prepared in good yields by carrying out the critical synthetic steps under power ultrasound (US) or microwave (MW) irradiation. Starting from azide and acetylenic CD derivatives, we exploited an efficient MW-promoted Huisgen 1,3-dipolar cycloaddition in the presence of Cu(I) salts. The resulting bridged CD derivatives gave stable adducts with magnetic-resonance-imaging contrast agents (MRI CAs) containing gadolinium(III) chelates. These inclusion complexes were found to be 2 to 3 orders of magnitude more stable than those formed by βCD and to be endowed with high relaxivity values.
A new access to homo- and heterodimers of α-, β-, and γ-cyclodextrin by a microwave-promoted huisgen cycloaddition
Cravotto, Giancarlo,Mendicuti, Francisco,Martina, Katia,Tagliapietra, Silvia,Robaldo, Bruna,Barge, Alessandro
scheme or table, p. 2642 - 2646 (2009/05/07)
A new and efficient synthetic protocol for the preparation of α-, β- and γ-cyclodextrin (CD) homo- and heterodimers is presented. A microwave-promoted Huisgen 1,3-dipolar cycloaddition will efficiently link together monoazido and monoacetylenic CD derivatives through a 1,2,3-triazole bridge. This well-known click reaction provides a versatile method to yield 'head-to-tail' and 'tail-to-tail' CD dimers in a broad range of combinations. Such an easy access to this kind of molecular architecture may be used to fashion ad hoc tailored CD cavities such as pinching-type structures to be exploited as nanosized reactors or molecular carriers. Preliminary estimates of the relative distances and orientations of the two CD units in each kind of dimer were obtained by molecular dynamics simulations and related calculations.
Synthetic 6-O-methylglucose-containing polysaccharides (sMGPs): Design and synthesis
Meppen, Malte,Wang, Yonghui,Cheon, Hwan-Sung,Kishi, Yoshito
, p. 1941 - 1950 (2007/10/03)
With the hope of mimicking the chemical and biological properties of natural 6-O-methyl-D-glucose-containing polysaccharides (MGPs), synthetic 6-O-methyl-D-glucose-containing polysaccharides (sMGPs) were designed and synthesized from α-, β-, and y-cyclode
Synthesis and characterisation of sulfated amphiphilic α-, β- and γ-cyclodextrins: Application to the complexation of acyclovir
Dubes, Alix,Degobert, Ghania,Fessi, Hatem,Parrot-Lopez, Helene
, p. 2185 - 2193 (2007/10/03)
The synthesis of sulfated amphiphilic α-, β- and γ-cyclodextrins was achieved according to the standard protection-deprotection procedure. The formation of inclusion complexes between the amphiphilic α-, β- and γ-cyclodextrins and an antiviral molecule, acyclovir (ACV) was investigated by UV-visible spectroscopy (UV-Vis) and electrospray ionisation mass spectrometry (ESIMS). UV-Vis spectroscopy allowed determination of the stoichiometry and stability constants of complexes, whereas ESIMS, a soft ionisation technique, allowed the detection of the inclusion complexes. The results showed that the non-sulfated amphiphilic cyclodextrins exhibit a 1:2 stoichiometry with acyclovir, while sulfated amphiphilic cyclodextrins, except γ-cyclodextrin, exhibit a 1:1 stoichiometry indicating the loss of one interaction site. Non-covalent interactions between acyclovir and non-sulfated amphiphilic cyclodextrins appear to take place both in the cavity of the cyclodextrin and inside the hydrophobic zone generated by alkanoyl chains. In contrast, in the case of sulfated amphiphilic cyclodextrins, the interactions appear to involve only the hydrophobic region of the alkanoyl chains.
Analysis of the Conformational Behaviour of Perfunctionalized β-Cyclodextrins. Part 1. Evidence for Insertion of one of the Rim Substituents into the Cyclodextrin Cavity in Organic Solvents
Jullien, Ludovic,Canceill, Josette,Lacombe, Liliane,Lehn, Jean-Marie
, p. 989 - 1002 (2007/10/02)
Several functionalized β-cyclodextrins have been shown to exhibit conformational isomerism.The analysis of the conformational behaviour of several derivatives strongly suggests that a slow exchange occurs between C7 and C1 conformers, the C1 probably invo
Selective chemical modification of cyclomalto-oligosaccharides via tert-butyldimethylsilylation
Takeo, Kenichi,Mitoh, Hisayoshi,Uemura, Kazuhiko
, p. 203 - 222 (2007/10/02)
Selective reaction of cyclomaltoheptaose and cyclomalto-octaose with tert-butylchlorodimethylsilane in N,N-dimethylformamide in the presence of inidazole gave the heptakis(6-O-tert-butyldimethylsilyl) (21) and octakis(6-O-tert-butyldimethylsilyl) (27) der
