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Upstream product

• 100-44-7 benzyl chloride 
• 7585-39-9 β‐cyclodextrin 

Downstream Products

• 142504-40-3 2^A,2^B,2^C,2^D,2^E,2^F,2^G,6^A,6^B,6^C,6^D,6^E,6^F,6^G-tetradeca-O-benzyl-β-cyclodextrin 
• 24679-79-6 2,3,6-Tri-O-benzyl-α-D-glucopyranose 

Relevant academic research and scientific papers

Towards the sequence-specific multivalent molecular recognition of cyclodextrin oligomers

Sequence-specific multivalent molecular recognition has been recognized to play a major role in biological processes. Furthermore, sequence-specific recognition motifs have been used in various artificial systems in the last years, e.g., to emulate biological processes or to build up new materials with highly specific recognition domains. In this article, we present the preparation of cyclodextrin (CD)-based strands and complementary and non-complementary strands modified with guest molecules and the investigation of their complexation behavior towards each other by isothermal titration calorimetry (ITC). As complementary binding motifs n-butyl and α-CD and adamantane and β-CD were selected. It was found that it is possible to realize sequencespecific molecular recognition by the use of host-guest chemistry, but the recognition motifs as well as the linkages have to be chosen very carefully. In the case of trivalent systems one adamantane moiety must be included to induce preferred formation of 1:1 adducts. Due to the too weak interaction between n-butyl and α-CD these systems have a negative chelate cooperativity and open adducts are preferentially formed. As soon as two adamantane moieties are present, the complementary systems have a positive chelate cooperativity and double-stranded structures are favored over open adducts. In this system the n-butyl moiety provides insufficient discrimination towards α- and β-CD and no sequence specificity is observed. By the combination of three adamantane moieties sequence specificity can be generated. Exclusively with the complementary CD sequence double-stranded structures are formed, with non-complementary strands aggregates of higher stoichiometry are generated.

Ultrasensitive QRS made by supramolecular assembly of functionalized cyclodextrins and graphene for the detection of lung cancer VOC biomarkers

A novel electronic nose system comprising functionalized β-cyclodextrin wrapped reduced graphene oxide (RGO) sensors with distinct ability of discrimination of a set of volatile organic compounds has been developed. Non-covalent modification of chemically functionalized cyclodextrin with RGO is carried out by using pyrene adamantane as a linker wherever necessary, in order to construct a supramolecular assembly. The chemical functionality on cyclodextrin is varied utilising the principle of selective chemical modification of cyclodextrin. In the present study, the combined benefits of the host-guest inclusion complex formation ability and tunable chemical functionality of cyclodextrin, as well as the high surface area and electrical conductivity of graphene, are utilized for the development of a set of highly selective quantum resistive chemical vapour sensors (QRS), which can be assembled in an electronic nose.

Array-based detection of isomeric and analogous analytes employing synthetically modified fluorophore attached β-cyclodextrin derivatives

Reported herein is a sensitive and selective array-based sensing strategy based on differential interactions with three supramolecular cyclodextrin-fluorophore sensors. Each interaction results in a distinct fluorescence modulation response, and linear discriminant analyses of these responses results in 100% successful classification of three classes of isomeric analytes and two classes of analogous analytes. Calculated limits of detection for this system are at or near literature-reported levels of concern.

Straightforward synthesis towards mono and bis-phosphonic acid functionalised β-cyclodextrins

For the first time a novel class of cyclodextrins bearing phosphonic acid groups has been revealed using a new versatile methodology. These derivatives can be easily synthesised in four easy steps starting from the diol with relatively high percentage yields and no difficult purification procedures. Chemical modifications were carried out in a controlled regioselective manner using a DIBAL promoted de-O-benzylation, followed by a modified Horner-Wadsworth-Emmons reaction to introduce the key phosphorus moieties. Fully deprotected products could have wide applications as useful tools in biological systems as well as key building blocks in complex cyclodextrin chemistry.

Dual emission of a bis(pyrene)-functionalized, perbenzylated β-cyclodextrin

A bis(pyrene)-functionalized β-cyclodextrin (1) has been prepared in two steps from perbenzylated β-cyclodextrin. This compound shows dual emission properties, which arise from the pyrenyl chromophores. Upon excitation of 1 at 355 nm, monomer blue fluorescence (386, 407 and 428 nm) is observed in DMSO solution, whereas excimer green fluorescence (477 nm) is seen upon addition of ≥20 vol% water in DMSO. This suggests that modified β-cyclodextrin 1 changes its shape in response to the environment. The sensing properties of 1 towards carboxylic acids and alcohols were investigated in H2O-DMSO (80: 20 v/v). Monomer fluorescence is restored selectively by medium length normal carboxylic acids, such as enanthic acid (C7) found in rancid oils and capric acid (C10), while both monomer and excimer emissions are enhanced by homologous alcohols, such as 1-heptanol, used in cosmetics and 1-decanol. Remarkably, bulkier substrates, such as tert-butyl alcohol or 1-adamantylcarboxylic acid are not detected. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

A hydrophilic cyclodextrin duplex forming supramolecular assemblies by physical cross-linking of a biopolymer

New β-cyclodextrin (β-CD) dimeric species have been synthesised in which the two CD moieties are connected by one or two hydrophilic oligo(ethylene oxide) spacers. Their complexation with sodium adamantylacetate (free adamantane) and adamantane-grafted chitosan (AD-chitosan) was then studied by different complementary techniques and compared with their hydrophobic counterparts that contain an octamethylene spacer. Isothermal titration calorimetry experiments have demonstrated that the use of hydrophilic spacers between the two CDs instead of aliphatic chains makes almost all of the CD cavities available for the inclusion of free adamantane. Investigation of the interaction of the CDs with AD-chitosan by viscosity measurements strongly suggests that the molecular conformation of the CD dimeric species plays a crucial role in their cross-linking with the biopolymer. The derivative doubly linked with hydrophilic arms, also called a duplex, has been shown to be a more efficient cross-linking agent than its singly bridged counterpart, referred to as a dimer. Hence, only 0.5 molar equivalents of the hydrophilic duplex with respect to adamantane was required to obtain the maximum viscosity, whereas in the case of the duplex with aliphatic spacers, the maximum viscosity was achieved with a [duplex]/[AD] ratio of about 1.7 (corresponding to a [CD]/ [AD] ratio of 2.5), but with a higher value. To clarify the relationships between the molecular architecture and complexation properties, computational studies were also performed that clearly confirmed the importance of double bridging.

Hexaphyrin-cyclodextrin hybrids: Getting larger, getting confused

The diversity of hexaphyrin-cyclodextrin hybrids (HCD), previously formed from the covalent assembly of regular hexaphyrin and α-cyclodextrin subunits, has been increased following two main directions: enlarging the confined space provided by the cyclodextrin and tuning the N-core of the hexaphyrin aiming at bimetallic complexes. The larger β-cyclodextrin unit was selectively functionalized with aldehyde linkers on its primary rim which were further reacted with 2 eq. of pentafluorophenyl tripyrrane in acidic conditions, followed by DDQ oxidation. Doubly-linked HCD hybrids were obtained with structural variations in the hexaphyrin macrocycles depending on the MSA concentration (2 vs. 200 mM) producing either regular ([26] rectangular/[28] M?bius) or doubly N-confused dioxo ([26] rectangular) scaffolds. For the latter, two isomers were isolated featuring mirror transoid skeletons and long-side meso-linking patterns, giving rise to planar chirality at the origin of intense and opposite electronic circular dichroism (ECD) spectra. Zn(II) complexation was then investigated leading to two main findings. (i) The regular [28] M?bius HCD afforded a mixture of monometallic M?bius Zn(II) complexes in the presence of acac ligand. ECD spectroscopy indicated a chirality transfer from the β-cyclodextrin favoring a P M?bius twist, but opposite to that arising from the narrower α-cyclodextrin congener (M twist favored). (ii) Owing to N3O coordination boxes, dissymmetric bimetallic Zn(II) complexes were readily formed with the doubly N-confused dioxo HCDs through a positive cooperative process. Both metal centers bind a DMAP ligand in axial positions, which is of interest for the

CAPPED CYCLODEXTRIN-HYDROPHOBIC MOIETY CONJUGATE, CYCLODEXTRIN SUPRAMOLECULAR POLYMER, AND CYCLODEXTRIN-siRNA COMPLEX AND METHOD OF SYNTHESIS THEREOF

The invention relates to a capped cyclodextrin-hydrophobic moiety conjugate, to a supramolecular polymer formed of capped cyclodextrin-hydrophobic moiety conjugates according to the invention and to a siRNA-cyclodextrin complex comprising a supramolecular polymer according to the invention. The invention also relates to a method for manufacturing the capped cyclodextrin-hydrophobic moiety conjugate, the supramolecular polymer, the siRNA-cyclodextrin complex according to the invention. The capped cyclodextrin-hydrophobic moiety conjugate of the invention comprises a capped cyclodextrin group and at least one hydrophobic moiety bound by a first linker to one of the carbon atoms of the cap. The invention can be used for various applications in particular in the pharmaceutical field.

Direct and Regioselective Di-α-fucosylation on the Secondary Rim of β-Cyclodextrin

A straightforward glycosylation method is described to regio- and stereoselectively introduce two α-l-fucose moieties directly to the secondary rim of β-cyclodextrin. Using NMR and MS fragmentation studies, the nonasaccharide structure was determined, which was also visualized using molecular dynamics simulations. The reported glycosylation method proved to be robust on gram-scale, and may be generally applied to directly glycosylate β-cyclodextrins to make well-defined multivalent glycoclusters.

Zinc and Copper Complexes of Methylated Di- and Tetraaminocyclodextrins

The α- and β-cyclodextrins with two dimethylamino groups or two trimethylethylenediamino groups attached to the primary face were synthesized and their pKa values were determined by potentiometric titration. The complexation of the four cyclodextrin analogues with zinc and copper was studied by NMR and showed one or two cyclodextrins bound to the metal. Inclusion of 4-halophenols in the metal complexes were also studied.