General method for preparing altrosides from 2,3-manno-epoxides and its application to synthesis of alternative β-cyclodextrin with an altroside as the constituent of macrocyclic structure

Fujita, Kahee; Ohta, Kouji; Ikegami, Yoshihiro; Shimada, Hideaki; Tahara, Tsutomu; Nogami, Yasuyoshi; Koga, Tomohiro; Saito, Kazuki; Nakajima, Terumi

doi:10.1016/0040-4039(94)88515-x

Cited by 45 publications

(16 citation statements)

References 15 publications

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“…The introduction of one altroside into the cyclodextrin caused unequivalency of the glucose units in the NMR spectrum. After the 3-functionalization in addition to the two groups of peaks observed in the 4.1-3.5 ppm region due to the CD protons, peaks are present at 2.81 and 4.14 ppm due to the H-3A and H-5A (A is the functionalized ring), The data compared with the calculated J for d-glucopyranosid rings suggest that the altrose residue is in an 1 C 4 0 S 2 4 C 1 conformational equilibrium shifted towards the 1 C 4 conformation, as typically described for this class of compounds [40][41][42][43]. The involvement of the NH group in the H-bond formation with 2-OH of B ring can be proposed, in the same way for the monoaltrocyclodextrins.…”

Section: Characterization Of the Ligand And Of The Copper Complexesmentioning

confidence: 89%

3-Amino derivative of β-cyclodextrin: thermodynamics of copper(II) complexes and exploitation of its enantioselectivity in the separation of amino acid racemates by ligand exchange capillary electrophoresis

Cucinotta

Giuffrida

Mendola

et al. 2004

Journal of Chromatography B

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Section: Characterization Of the Ligand And Of The Copper Complexesmentioning

confidence: 89%

3-Amino derivative of β-cyclodextrin: thermodynamics of copper(II) complexes and exploitation of its enantioselectivity in the separation of amino acid racemates by ligand exchange capillary electrophoresis

Cucinotta

Giuffrida

Mendola

et al. 2004

Journal of Chromatography B

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“…The 1 C 4 conformation of altrose unit a might be stabilized by a hydrogen bond between the hydroxyl group at C-2 of the altrose unit and the OH group at C-3 of the adjacent glucose unit. [12] However, there is no experimental evidence to support such a hydrogen bond. An extra indication that the 4 C 1 conformation of h in water is stabilized by the self-inclusion of the spacer is obtained from the coupling constant of the H-1 protons of units a and h (for both units J 12 7.1 Hz) of compound 2 dissolved in [D 6 ]DMSO.…”

mentioning

confidence: 96%

Synthesis, Conformation, and Binding Properties of Cyclodextrin Homo- and Heterodimers Connected through Their Secondary Sides

et al. 1998

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The synthesis of homo-and heterocyclodextrin (CD) dimers, containing two CD moieties that are linked through their secondary sides by aliphatic or 2,2'-bipyridyl spacers is described. In these dimers, the glucose units to which the spacers are linked have been transformed into altrose units. The dimers with an octamethylene spacer show self-complexation of the spacer in one of the CD moieties in aqueous solution, as revealed by 1 H and 13 C NMR spectroscopy. Using high-resolution (600 and 800 MHz) NMR spectroscopy and a variety of 2D NMR techniques, an assignment of nearly all of the 1 H NMR signals of two of the CD dimers was made, affording detailed information about the structure of these compounds in water. The self-inclusion of the spacers leads to lower binding affinities for ditopic guest molecules like p-toluidino-6-naphthalene sulfonate (TNS) derivatives and porphyrins. When a rigid 2,2'-bipyridyl group is used to connect the two CD moieties, self-inclusion of the spacer is not possible. This results in the formation of different complexes with ditopic guest molecules, for example, a 2:2 complex with a porphyrin. The CD heterodimers described in this paper contain an a-CD and a b-CD moiety. These dimers display site-specific binding of guest molecules.

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“…Previously, we have reported the formation of pseudo [1]rotaxane dimer from the altro-a-CD (altro-a-CD) dimer via tumbling of altro-a-CD, 40,41 which consists of one altropyranose unit and five glucopyranose units. Although some research groups have reported the tumbling of permethylated glucopyranose type CD, [42][43][44][45][46][47] tumbling of the altropyranose unit in altro-CDs has yet to be reported. We have successfully observed the selective emission of PDI-CD 2 s in aqueous solutions and prepared emission films based on PDI-CD 2 s kneaded into polyvinyl alcohol (PVA) films.…”

Section: Introductionmentioning

confidence: 99%

Emission properties of cyclodextrin dimers linked with perylene diimide—effect of cyclodextrin tumbling

Takashima

Otsubo

et al. 2012

Polym J

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Perylene diimide (PDI) derivatives with cyclodextrins (PDI-CD 2 s) exhibit specific emission properties, which depend on the type of CDs in an aqueous solution. Herein we successfully create an emission film-kneaded PDI-CD 2 derivatives via effective tumbling of the altropyranose unit. PDI-6CD 2 s are crosslinked with PDI between 6-amino-CDs. Although the emission intensities of PDI-6CD 2 s in dimethyl sulfoxide are similar regardless of the type of CD, PDI-6cCD 2 has a relatively high emission intensity in aqueous solutions. In contrast, for PDIC 7 -3CD 2 s, which are linked with N,N'-bis(6-carboxylhexyl)perylene-3,4,9,10-tetracarboxyl diimide (BisC 7 -PDI) between 3-amino-CDs, the emission intensity of PDIC 7 -3bCD 2 is stronger than those of PDIC 7 -3aCD 2 , PDIC 7 -3cCD 2 , and PDI-6CD 2 s in aqueous solutions. The selective emission behavior of PDIC 7 -3CD 2 s is due to the formation of the pseudo[1]rotaxane dimer through tumbling of the altropyranose unit in an aqueous solution. PDIC 7 -3bCD 2 in the solid state does not demonstrate a distinctive emission due to self-quenching, whereas PDIC 7 -3bCD 2 kneaded into the polyvinyl alcohol (PVA) film exhibits a bright yellow emission. The order of the emission intensities of PDIC 7 -3CD 2 s kneaded into PVA films is similar to those in aqueous solutions. INTRODUCTIONRecently, supramolecular assemblies with extended aromatic compounds have attracted much attention. 1-4 Perylene diimides (PDIs) derivatives effectively form supramolecular assemblies through p-p stacking interaction. [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] In particular, supramolecular assemblies based on calixarenePDI conjugates show efficient energy and electron transfer properties due to the well-defined rigid and electron-rich scaffolds of calixarenes. [22][23][24][25][26][27] We have prepared PDI derivatives with a high emission property in aqueous solutions.Generally, PDI derivatives have low solubilities in aqueous solutions. Even if PDI derivatives are dissolved in aqueous solutions by introducing a hydrophilic group, the emission of PDI derivatives exhibit self-quenching in aqueous solutions due to the formation of supramolecular assemblies and folders. To create water-soluble and effective emission sensor materials with PDI derivatives, we have introduced CDs into the PDI motif. The CDs are a family of macrocyclic oligosaccharides; the most common are composed of 6 (a), 7 (b), or 8 (g) a-1,4-linked D-glucopyranose units. [28][29][30][31][32][33][34] The introduction of CDs should influence the molecular recognition property and increase the emission intensity. Although supramolecular assemblies based on permethylated CDPDI conjugates have been previously reported, 35-38 the formation of assemblies cannot prevent the decrease in the monomer emission intensity of the PDI units due

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General method for preparing altrosides from 2,3-manno-epoxides and its application to synthesis of alternative β-cyclodextrin with an altroside as the constituent of macrocyclic structure

Cited by 45 publications

References 15 publications

3-Amino derivative of β-cyclodextrin: thermodynamics of copper(II) complexes and exploitation of its enantioselectivity in the separation of amino acid racemates by ligand exchange capillary electrophoresis

3-Amino derivative of β-cyclodextrin: thermodynamics of copper(II) complexes and exploitation of its enantioselectivity in the separation of amino acid racemates by ligand exchange capillary electrophoresis

Synthesis, Conformation, and Binding Properties of Cyclodextrin Homo- and Heterodimers Connected through Their Secondary Sides

Emission properties of cyclodextrin dimers linked with perylene diimide—effect of cyclodextrin tumbling

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