Controlled Stability of the Triple‐Stranded Helical Structure of a β‐1,3‐Glucan with a Chromophoric Aromatic Moiety at a Peripheral Position

Ikeda, Masato; Haraguchi, Shuichi; Numata, Munenori; Shinkai, Seiji

doi:10.1002/asia.200700150

Cited by 12 publications

(5 citation statements)

References 74 publications

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“…850 A Curdlan derivative bearing an aromatic pendant at the 6 position of the glucose unit (537a in Figure 165A) also forms a triple-stranded helical structure in a DMSO solution containing water or methanol, and the pendant groups are helically aligned to form an H-type aggregation (Figure 165B). 851 Moreover, the reversible structural modulation of 537a between the singleand triple-stranded helical structures has been realized by the alternate addition of Zn 2+ ions or 1,4,8,11-tetraazacyclotetradecane in a DMSO/methanol mixture (1/1, v/v). On the other hand, an amphoteric Curdlan derivative bearing both amino and carboxyl groups (537b) has been reported to show pHdependent structural transformations among the singlestranded random-coil, triple-stranded helical structure, and aggregate structures.…”

Section: Chemical Reviewsmentioning

confidence: 99%

“…A Curdlan derivative bearing an aromatic pendant at the 6 position of the glucose unit ( 537a in Figure A) also forms a triple-stranded helical structure in a DMSO solution containing water or methanol, and the pendant groups are helically aligned to form an H-type aggregation (Figure B) . Moreover, the reversible structural modulation of 537a between the single- and triple-stranded helical structures has been realized by the alternate addition of Zn 2+ ions or 1,4,8,11-tetraazacyclotetradecane in a DMSO/methanol mixture (1/1, v/v).…”

Section: Helical Polymers and Their Assembliesmentioning

confidence: 99%

Section: Helical Polymers and Their Assembliesmentioning

confidence: 99%

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Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions

et al. 2016

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In this review, we describe the recent advances in supramolecular helical assemblies formed from chiral and achiral small molecules, oligomers (foldamers), and helical and nonhelical polymers from the viewpoints of their formations with unique chiral phenomena, such as amplification of chirality during the dynamic helically assembled processes, properties, and specific functionalities, some of which have not been observed in or achieved by biological systems. In addition, a brief historical overview of the helical assemblies of small molecules and remarkable progress in the synthesis of single-stranded and multistranded helical foldamers and polymers, their properties, structures, and functions, mainly since 2009, will also be described.

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Section: Chemical Reviewsmentioning

confidence: 99%

Section: Helical Polymers and Their Assembliesmentioning

confidence: 99%

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Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions

et al. 2016

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“…We have established site-selective and quantitative modification of the 6-OH group in native Curdlan using “Click Chemistry” . Cur-oeg was synthesized according to the similar procedure (for the detail see Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Thermo- and Solvent-Responsive Polymer Complex Created from Supramolecular Complexation between a Helix-Forming Polysaccharide and a Cationic Polythiophene

et al. 2010

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The helical structure is one of key structural components for both biological systems and artificial chiral systems. So far, we have succeeded in fabricating "tight" insulated molecular wires consisting of a triple-stranded cohelical structure formed through supramolecular wrapping of synthetic polymers by a helix-forming polysaccharide (schizophyllan). Herein, we have designed a new modified polysaccharide (Cur-oeg) to form a "loose" macromolecular complex with a conjugated polymer (CP) that allows structural changes in response to external stimuli. Cur-oeg forms a helical complex with an achiral cationic polythiophene (PT1), and the effective conjugation length is changed by temperature, showing a large absorption peak shift from 403 to 482 nm between 85 and 5 °C. According to the change in the conjugation system, the fluorescence and the induced circular dichroism show the continuous spectral shifts under temperature control. The color changes in the absorption and the fluorescence are detectable with observation by the naked eye and are reversibly controlled under thermal cycles, indicating that this system has the function of a "molecular thermometer". It is shown that the induced thermoresponsiveness is associated with structural rearrangement of the helical conformation of PT1 in the complex. Moreover, another unique responsiveness is discovered for the film state: that is, the film color is varied when it is exposed to the vapor of water or methanol (vaporchromism), resulting from the structural change of PT1 occurring even in the film state. These flexible molecular motions in both the solution state and the film state can be applicable to the design of CP-based smart sensors, polarized materials, switching devices, etc.

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“…Therefore, stimuli-responsive motifs introduced into the C6 position have realized the control of assembling/disassembling interconversion in CUR derivatives. For example, a CUR derivative bearing dialkylaniline groups and diethylene glycol groups was assembled by the addition of Zn 2+ , 8 and poly-NIPAM-appended CUR showed heat-responsiveness in the wrapping process of carbon nanotubes. 9 More recently, we have reported the unique chromo-sensors based on the PEGylated CUR co-helically complexed with polythiophene; as the conformation of the helical complex changes in response to heat in aqueous solution or to moisture in the solid state, the environmental change can be easily monitored by a color change arising from complexed polythiophene.…”

Section: Introductionmentioning

confidence: 99%

Giant amino acids designed on the polysaccharide scaffold and their protein-like structural interconversion

et al. 2014

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Amphoteric β-1,3-glucans possessing both amino groups and carboxylic acid groups on the C6 positions of glucose units were designed and synthesized from naturally produced curdlan. The amphoteric polysaccharides showed the isoelectric point and the pH responsive interconversion between the original triple helix and single-stranded random structures. Since the pH dependences are comparable to the typical properties of proteins, the polysaccharides can be considered as a new class of giant amino acids. Utilizing the pH responsiveness, pH-controlled catch-and-release has been realized for cationic peptides or anionic DNA. We believe that the amphoteric polysaccharide can act as a new potential polymer to construct stimuli-responsive smart materials on the basis of the polysaccharide scaffold.

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Controlled Stability of the Triple‐Stranded Helical Structure of a β‐1,3‐Glucan with a Chromophoric Aromatic Moiety at a Peripheral Position

Cited by 12 publications

References 74 publications

Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions

Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions

Thermo- and Solvent-Responsive Polymer Complex Created from Supramolecular Complexation between a Helix-Forming Polysaccharide and a Cationic Polythiophene

Giant amino acids designed on the polysaccharide scaffold and their protein-like structural interconversion

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