A New Glycorotaxane Molecular Machine Based on an Anilinium and a Triazolium Station

Coutrot, Frédéric; Busseron, Eric

doi:10.1002/chem.200800480

Cited by 115 publications

(72 citation statements)

References 46 publications

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“…Example A In the study of glycorotaxanes as corresponding molecular muscles 85 and machines, 86 the two large amplitude mannosyl [2]rotaxane molecular machines 56a,b have been synthesized from mannosylpyridinium azide 57a,b and the alkyne 58 in the presence of dibenzo [24]crown-8 (DB24C8) by using click chemistry. 87 Their thread bears two stations: an anilinium and a monoor disubstituted pyridinium amide, and the ring is DB24C8 (Scheme 13).…”

Section: Scheme 12mentioning

confidence: 99%

Rotaxanes and pseudorotaxanes with threads containing pyridinium units

Deska¹,

Kozłowska²,

Śliwa³

2013

Arkivoc

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In this review, a continuation of an earlier one concerning rotaxanes with threads containing viologen units, the syntheses and properties of rotaxanes with threads bearing quaternary pyridinium units are described, along with their possible applications. In the first part rotaxanes containing bis(dipyridiniumyl)ethane unit in the thread are presented; they include species with stoppers incorporating metal complexes. The second part concerns rotaxanes formed by anion templation, they are divided into those involving the Grubbs RCM procedure for construction of a ring, and those employing rings built by condensation reactions. Then rotaxanes synthesized with the use of previously prepared rings are described. The third part deals with rotaxane molecular machines, especially those bearing mannosyl moieties. In the last part pseudorotaxanes containing crown ether based cryptands as rings, are shown.

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Section: Scheme 12mentioning

confidence: 99%

Rotaxanes and pseudorotaxanes with threads containing pyridinium units

Deska¹,

Kozłowska²,

Śliwa³

2013

Arkivoc

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“…Recently, Coutrot et al used the copper(I)-catalyzed Huisgen alkyne-azide 1,3-dipolar cycloaddition to end-cap a [2]rotaxane using an azide-containing mannopyranose blocking group [42,43]. The advantage of this reaction is the possibility to perform the reaction at room temperature, in opposition to the mild heating needed for the same reaction without copper (I) catalyst [41].…”

Section: Scheme 12 Rotaxane Formation Through 13-dipolarcycloadditionmentioning

confidence: 99%

“…This particular molecule of higher degree of freedom could be of particular interest in biological events in which multivalent interaction is desired for ligand/receptor recognition. Using the same click strategy, Coutrot et al were also the first to explore the possibility of creating an efficient second station for the DB24C8 by alkylation of the triazole, with the aim of synthesizing molecular machines [43].…”

Section: Scheme 12 Rotaxane Formation Through 13-dipolarcycloadditionmentioning

confidence: 99%

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Recent Advances in the Synthesis of Ammonium-Based Rotaxanes

Thibeault

Morin

2010

Molecules

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Abstract:The number of synthetic methods enabling the preparation of ammonium-based rotaxanes has increased very rapidly in the past ten years. The challenge in the synthesis of rotaxanes results from the rather weak interactions between the ammonium-containing rod and the crown ether macrocycle in the pseudorotaxane structure that rely mostly on O·H hydrogen bonds. Indeed, no strong base or polar solvent that could break up H-bonding can be used during the formation of rotaxanes because the two components will separate as two distinct entities. Moreover, most of the reactions have to be performed at room temperature to favor the formation of pseudorotaxane in solution. These non-trivial prerequisites have been taken into account to develop efficient reaction conditions for the preparation of rotaxanes and those are described in detail along this review.

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“…The molecular machinery described in this paper is based on interactions between a crown ether macrocycle and our already reported system of molecular stations [42]. Indeed, the lasso compound is composed of a benzometaphenylene [25]crown-8 (BMP25C8) [43][44][45][46] macrocycle which surrounds a molecular axle containing two molecular stations for the BMP25C8.…”

Section: Introductionmentioning

confidence: 99%

A pH-Sensitive Peptide-Containing Lasso Molecular Switch

2013

Self Cite

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Abstract:The synthesis of a peptide-containing lasso molecular switch by a selfentanglement strategy is described. The interlocked [1] rotaxane molecular machine consists of a benzometaphenylene [25]crown-8 (BMP25C8) macrocycle surrounding a molecular axle. This molecular axle contains a tripeptidic sequence and two molecular stations: a N-benzyltriazolium and a pH-sensitive anilinium station. The tripeptide is located between the macrocycle and the triazolium station, so that its conformation can be tailored depending on the shuttling of the macrocycle from one station to the other. At acidic pH, the macrocycle resides around the anilinium moiety, whereas it shuttles around the triazolium station after deprotonation. This molecular machinery thus forces the lasso to adopt a tightened or a loosened conformation.

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A New Glycorotaxane Molecular Machine Based on an Anilinium and a Triazolium Station

Cited by 115 publications

References 46 publications

Rotaxanes and pseudorotaxanes with threads containing pyridinium units

Rotaxanes and pseudorotaxanes with threads containing pyridinium units

Recent Advances in the Synthesis of Ammonium-Based Rotaxanes

A pH-Sensitive Peptide-Containing Lasso Molecular Switch

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