Molecular Puzzle Ring: <i>pseudo</i>[1]Rotaxane from a Flexible Cyclodextrin Derivative

Miyawaki, Atsuhisa; Kuad, Paul; Takashima, Yoshinori; Yamaguchi, Hiroyasu; Harada, Akira

doi:10.1021/ja806620z

Cited by 46 publications

(31 citation statements)

References 32 publications

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“…From a flexible cyclodextrin derivative (Miyawaki, et al, 2008b) CDs threaded onto a polymer chain TOF Pseudo-rotaxane-CDs (Osaki, et al, 2007b) TOF (DHB) Pyrene-CD adduct For synthesis of CD-carbon nanotube hybrids (Ogoshi, et al, 2007) [2]Rotaxanes bearing α-cyclodextrin derivatives TOF…”

Section: Maldi Osw Saponinsmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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This review is the fifth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2008. The first section of the review covers fundamental studies, fragmentation of carbohydrate ions, use of derivatives and new software developments for analysis of carbohydrate spectra. Among newer areas of method development are glycan arrays, MALDI imaging and the use of ion mobility spectrometry. The second section of the review discusses applications of MALDI MS to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, biopharmaceuticals, glycated proteins, glycolipids, glycosides and various other natural products. There is a short section on the use of MALDI mass spectrometry for the study of enzymes involved in glycan processing and a section on the use of MALDI MS to monitor products of the chemical synthesis of carbohydrates with emphasis on carbohydrate-protein complexes and glycodendrimers. Corresponding analyses by electrospray ionization now appear to outnumber those performed by MALDI and the amount of literature makes a comprehensive review on this technique impractical. However, most of the work relating to sample preparation and glycan synthesis is equally relevant to electrospray and, consequently, those proposing analyses by electrospray should also find material in this review of interest.

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Section: Maldi Osw Saponinsmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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“…The pseudo prefix denotes the ability of these species to establish an equilibrium between disentangled conformations and self-entangled conformations, wherein the macrocycle is threaded by its own tail. When such a molecule takes on a tail-threaded conformation, it is a pseudo [1]rotaxane. 1 In the presence of sufficient barriers within disentanglement pathways, a given species will be trapped in a self-entangled state; such a species is a [1]rotaxane.…”

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“…There are several distinct mechanisms by which a disentangled pseudo [1]rotaxane may self-entangle. A mechanism of self-threading that can be envisioned, perhaps most readily, is one in which the terminus of the tail-like chain is seen to approach, fill, and pass through the cavity of the macrocycle, i.e., by an unassisted, endin, threading mechanism.…”

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confidence: 99%

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Actuator Prototype: Capture and Release of a Self-Entangled [1]Rotaxane

Xue

Mayer

2010

J. Am. Chem. Soc.

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A conformationally dynamic chain compound that rapidly and reversibly samples both self-entangled and disentangled conformations, yet favors disentangled conformations, and an exclusively self-entangled [1]rotaxane were separately prepared and characterized. The conformationally dynamic state and the conformationally locked state were shown to reversibly and controllably interconvert under appropriate conditions, with an accompanying observable change in size that was calculated to approximate a 35% contraction in length upon capture of the self-entangled state.

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“…To obtain experimental evidence for whether or not a certain moiety can pass through the cavity of CDs, the behavior of complex formation of CDs with a dumbbell molecule possessing the moieties at both ends should be investigated. 57 Thus, this study deals with the complex formation of CDs with a dumbbell molecule bearing ferrocene moieties at both ends, FcC10Fc (Scheme 1).…”

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confidence: 99%

Complex Formation of Cyclodextrins with a Dumbbell Molecule Bearing Two Ferrocene Moieties at the Ends

Yamamoto¹,

Oi²,

Hashidzume³

et al. 2011

Bulletin of the Chemical Society of Japan

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The complexation behavior of cyclodextrins (CDs) with a dumbbell molecule possessing ferrocene (Fc) moieties at both the ends (FcC10Fc) was investigated by 1 H NMR, two-dimensional rotating frame Overhauser spectroscopy, circular dichroism spectroscopy, and cyclic voltammetry. ¡-CD includes the cyclopentadienyl rings of the Fc moiety shallowly from the wider side but not the decamethylene (C10) moiety, whereas ¢-CD and £-CD include not only the Fc moiety but also the C10 moiety. These observations indicate that the Fc moiety can pass through ¢-CD and £-CD cavities but not the ¡-CD cavity.Biological systems maintain their living activities using supramolecular assemblies responsive to external stimuli, which are responsible for various functions.13 These biological stimuli-responsive supramolecular assemblies have inspired a number of research groups to devote their efforts to construction of artificial supramolecular assemblies responsive to external stimuli, e.g., temperature, pH, chemicals, and light. 422Compared to thermo-, pH-, chemical-, and photo-responsive supramolecular assemblies, redox-responsive ones have been an underexamined subject of investigation, although redox stimulus is promising because it can be provided not only chemically by adding oxidants or reductants but also electrochemically by applying a potential. 2325Cyclodextrins (CDs) are cyclic oligomers of D-(+)-glucopyranose units linked through an ¡-1,4-glycoside bond (Scheme 1). CDs of 6, 7, and 8 glucopyranose units are called ¡-CD, ¢-CD, and £-CD, respectively. CDs are toroidal with narrower primary hydroxy and wider secondary hydroxy sides. The most important features of CDs are their hydrophilic exterior and hydrophobic cavity, and thus CDs recognize hydrophobic compounds of size and shape matching their cavity to form inclusion complexes in aqueous media. Since CDs are soluble in water and nontoxic, they are investigated widely as a building block for supramolecular assemblies. 2634A number of examples of CD-based supramolecular assemblies responsive to external stimuli have been also reported. 2731,33,34 It is known that CDs and ferrocene are a molecular recognition pair responsive to redox stimulus: CDs interact with the reduced form, ferrocene, to form inclusion complexes, but not with the oxidized form, ferrocenium.3554 Using pairs of CDs and ferrocene moieties, redox-responsive hydrogel, 55 controlled release, 56 and vesicle 53 have been realized. In order to construct more sophisticated redox-responsive supramolecular assemblies, e.g., Janus [2]rotaxanes and molecular shuttles, it is necessary to obtain fundamental data including not only how strong they interact (i.e., association constants) but also whether or not a ferrocene moiety can pass through the cavity of CDs. To the best of our knowledge however, there has been no research clarifying the latter point. To obtain experimental evidence for whether or not a certain moiety can pass through the cavity of CDs, the behavior of complex formation of CDs with a dumbbell molecule...

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Molecular Puzzle Ring: pseudo[1]Rotaxane from a Flexible Cyclodextrin Derivative

Cited by 46 publications

References 32 publications

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Actuator Prototype: Capture and Release of a Self-Entangled [1]Rotaxane

Complex Formation of Cyclodextrins with a Dumbbell Molecule Bearing Two Ferrocene Moieties at the Ends

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