A reliable synthesis of 2- and 6-amino-β-cyclodextrin and permethylated-β-cyclodextrin

Muderawan, I Wayan; Ong, Teng Teng; Lee, Teck Chia; Young, David J.; Ching, Chi Bun; Ng, Siu‐Choon

doi:10.1016/j.tetlet.2005.09.099

Cited by 52 publications

(34 citation statements)

References 10 publications

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“…Heptakis(2,3-di-O-methyl)-hexakis(6-O-methyl)-6-monodeoxy-6-monoazido-b-CD 8 and heptakis(2,3-di-O-methyl)-hexakis (6-O-methyl)-6-monodeoxy-6-monoamino-b-CD 3 were prepared according to literature. 20 Synthetic procedures and spectral data of new compounds (1, 5, 9, 10, 12, 13 and 17), and experimental details of complexation study are described in Supporting Information.…”

Section: Experimental Procedures Materialsmentioning

confidence: 99%

Modulation of reversible self-assembling of dumbbell-shaped poly(ethylene glycol)s and β-cyclodextrins: precipitation and heat-induced supramolecular crosslinking

Kobayashi

Katoono

Yamaguchi

et al. 2011

Polym J

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A series of dumbbell-shaped poly(ethylene glycol) (PEG) chains 1 attached to bulky end groups were prepared, and some of the chains formed supramolecular assemblies with b-cyclodextrin (b-CD) and its multiple, ditopic and tetratopic, derivatives. The chains with proper end groups successfully allowed b-CD to be trapped onto PEG through formation of hydrogen bonds at room temperature and higher. Mixing of the PEG chain and the ditopic supramolecular crosslinker in water at 40 1C led to a change in solution property from viscous to elastic, accompanied by a significant increase in viscosity, whereas this change was not induced at room temperature. A supramolecular network formed only when the PEG chain was mixed with the tetratopic supramolecular crosslinker at 40 1C. Once formed, the supramolecular crosslinking was maintained even after the system cooled down. Instead, dilution and shaking at room temperature resulted in a return to a solution with low viscosity. These assemblies and dissociations were affected by the end groups of 1.

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Section: Experimental Procedures Materialsmentioning

confidence: 99%

Modulation of reversible self-assembling of dumbbell-shaped poly(ethylene glycol)s and β-cyclodextrins: precipitation and heat-induced supramolecular crosslinking

Kobayashi

Katoono

Yamaguchi

et al. 2011

Polym J

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“…Although authors often do not differentiate between 2 A -azido-2 A -deoxy-manno--CD, 2 A -azido-2 A -deoxy-altro--CD and 2 A -azido-2 A -deoxy--CD, [118,122,123] the cyclodextrin with one mannosidic or altrosidic subunit could have the cavity slightly distorted and could be less acid-resistant than the native -CD. [120] Moreover, Martina et al [124] found the 2 A -azido-2 A -deoxy-manno--CD synthesised by Poon et al [123] to be the 3 A derivative rather than the 2 A derivative.…”

Section: Synthesis Of Derivatives Substituted At Positionmentioning

confidence: 99%

“…[122,125,126] 2 A -Amino-2 A -deoxy--CD was prepared by the insertion of a new substituted glucose unit into the α-CD ring (Scheme 1). [122,125,126] 2 A -Amino-2 A -deoxy--CD was prepared by the insertion of a new substituted glucose unit into the α-CD ring (Scheme 1).…”

Section: Synthesis Of Derivatives Substituted At Positionmentioning

confidence: 99%

Monosubstituted Cyclodextrins as Precursors for Further Use

Řezanka

2016

Eur J Org Chem

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Cyclodextrin derivatives find use in a broad field of applications (e.g., nanomaterials, biomedical applications, catalysis, separation techniques, sensors etc.), with monosubstitution allowing cyclodextrins to be attached to various types of surfaces or for a new feature to be introduced onto a cyclodextrin skeleton (recognition, catalysis, …). Although an enormous number of monosubstituted cyclodextrin derivatives have been synthesised, this review focuses only on the synthesis of several interesting monosubstituted derivatives (allyl, cinnamyl, propargyl, formylmethyl, carboxymethyl, azido and amino) suitable for further modifications. These derivatives allow the synthesis of an unlimited number of desired cyclodextrin derivatives. Using a cyclodextrin derivative already monosubstituted with a suitable functional group is much easier than the optimisation of monosubstitution for every new cyclodextrin derivative desired.

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“…Thus, we designed the dumbbell-shaped PEG derivatives 1 with a benzoyl group at each end, and the b-CD dimer 2 consisting of 3 [12] attached to each end of another PEG spacer, as illustrated in Figure 1. Here we report the heatinduced supramolecular crosslinking of dumbbell-shaped PEG with b-CD dimer, for the design of a novel class of thermoresponsive materials, based on reversible loose-fit rotaxanation between mismatched components at an elevated temperature.…”

Section: Introductionmentioning

confidence: 99%

Heat‐induced Supramolecular Crosslinking of Dumbbell‐shaped PEG with β‐CD Dimer Based on Reversible Loose‐fit Rotaxanation

Katoono

Kobayashi

Yamaguchi

et al. 2010

Macro Chemistry & Physics

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Supramolecular crosslinking was studied in reversible loose‐fit rotaxanation between a size‐mismatched ring and a dumbbell‐shaped chain attached to bulky terminals through slipping of the crosslinked rings onto the chain using a combination of β‐cyclodextrin (β‐CD) and poly(ethylene glycol) (PEG) in water. The mixing led to a drastic increase in viscosity only at an elevated temperature, while a PEG chain without any terminals or with bulkier terminals produced no change in the mixed solution under the same conditions. The dynamic viscoelastic properties of the mixed solution of the proper dumbbell‐shaped PEG chain and β‐CD dimer in water were also investigated to indicate network formation through heat‐induced supramolecular crosslinking. magnified image

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A reliable synthesis of 2- and 6-amino-β-cyclodextrin and permethylated-β-cyclodextrin

Cited by 52 publications

References 10 publications

Modulation of reversible self-assembling of dumbbell-shaped poly(ethylene glycol)s and β-cyclodextrins: precipitation and heat-induced supramolecular crosslinking

Modulation of reversible self-assembling of dumbbell-shaped poly(ethylene glycol)s and β-cyclodextrins: precipitation and heat-induced supramolecular crosslinking

Monosubstituted Cyclodextrins as Precursors for Further Use

Heat‐induced Supramolecular Crosslinking of Dumbbell‐shaped PEG with β‐CD Dimer Based on Reversible Loose‐fit Rotaxanation

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