Chirality inversion, supramolecular hydrogelation and lectin binding of two thiolactose amphiphiles constructed on a di-lauroyl-<scp>l</scp>-tartaric acid scaffold

Cano, María Emilia; Chenna, Pablo H. Di; Lesur, David; Wolosiuk, Alejandro; Kovensky, José; Uhrig, Marı́a Laura

doi:10.1039/c7nj02941a

Cited by 15 publications

(20 citation statements)

References 46 publications

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“…The disparities with the gelation properties of the two classes of disaccharides could possibly be associated with the structural pattern of the sugar groups [41]. Cano et al designed and synthesized two thiolactose-based amphiphilic LMWGs [86]. The two amphiphiles were built from a di-lauroyl-L-tartaric acid scaffold and only differed in the length of the ethylene glycol linker (Figure 40).…”

Section: Disaccharide Derivatives and Glycoclusters 271 Disaccharimentioning

confidence: 99%

“…The ability of the amphiphiles to bind to peanut agglutinin (Pna) lectin was also studied using a turbidimetric method and agglutination was observed in both cases. The structural parameters impacting amphiphilic self-assembly were explored in this study, contributing to knowledge that could be used in rationally Cano et al designed and synthesized two thiolactose-based amphiphilic LMWGs [86]. The two amphiphiles were built from a di-lauroyl-L-tartaric acid scaffold and only differed in the length of the ethylene glycol linker (Figure 40).…”

Section: Disaccharide Derivatives and Glycoclusters 271 Disaccharimentioning

confidence: 99%

“…The structural parameters impacting amphiphilic self-assembly were explored in this study, contributing to knowledge that could be used in rationally designing nanostructures which expose specific sugar ligands. Cano et al designed and synthesized two thiolactose-based amphiphilic LMWGs [86]. The two amphiphiles were built from a di-lauroyl-L-tartaric acid scaffold and only differed in the length of the ethylene glycol linker (Figure 40).…”

Section: Disaccharide Derivatives and Glycoclusters 271 Disaccharimentioning

confidence: 99%

“…Dendritic structures have been shown to be effective in the generation of LMOGs Figure 40. Structures of thiolactose-based amphiphilic gelators [86], n is the number of repeating unit.…”

Section: Disaccharide Derivatives and Glycoclusters 271 Disaccharimentioning

confidence: 99%

“…Structures of thiolactose-based amphiphilic gelators[86], n is the number of repeating unit.2.7.2. Branched Glycoclusters from Glycosyl Azides.…”

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confidence: 99%

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Recently Developed Carbohydrate Based Gelators and Their Applications

Morris

Bietsch

Bashaw

et al. 2021

Gels

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Carbohydrate based low molecular weight gelators have been an intense subject of study over the past decade. The self-assembling systems built from natural products have high significance as biocompatible materials and renewable resources. The versatile structures available from naturally existing monosaccharides have enriched the molecular libraries that can be used for the construction of gelators. The bottom-up strategy in designing low molecular weight gelators (LMWGs) for a variety of applications has been adopted by many researchers. Rational design, along with some serendipitous discoveries, has resulted in multiple classes of molecular gelators. This review covers the literature from 2017–2020 on monosaccharide based gelators, including common hexoses, pentoses, along with some disaccharides and their derivatives. The structure-based design and structure to gelation property relationships are reviewed first, followed by stimuli-responsive gelators. The last section focuses on the applications of the sugar based gelators, including their utilization in environmental remediation, ion sensing, catalysis, drug delivery and 3D-printing. We will also review the available LMWGs and their structure correlations to the desired properties for different applications. This review aims at elucidating the design principles and structural features that are pertinent to various applications and hope to provide certain guidelines for researchers that are working at the interface of chemistry, biochemistry, and materials science.

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Section: Disaccharide Derivatives and Glycoclusters 271 Disaccharimentioning

confidence: 99%

Section: Disaccharide Derivatives and Glycoclusters 271 Disaccharimentioning

confidence: 99%

Section: Disaccharide Derivatives and Glycoclusters 271 Disaccharimentioning

confidence: 99%

“…Dendritic structures have been shown to be effective in the generation of LMOGs Figure 40. Structures of thiolactose-based amphiphilic gelators [86], n is the number of repeating unit.…”

Section: Disaccharide Derivatives and Glycoclusters 271 Disaccharimentioning

confidence: 99%

“…Structures of thiolactose-based amphiphilic gelators[86], n is the number of repeating unit.2.7.2. Branched Glycoclusters from Glycosyl Azides.…”

mentioning

confidence: 99%

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