Alkyl triazole glycosides (ATGs)—A new class of bio-related surfactants

Sani, Faramarz Aliasghari; Heidelberg, Thorsten; Hashim, Roslan; Farhanullah,

doi:10.1016/j.colsurfb.2012.03.030

Cited by 31 publications

(24 citation statements)

References 28 publications

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“…Although the applied synthetic scheme suffers of high production costs owing to the number of reaction steps, the latter may be substantially reduced by application of a Fischer glycosylation approach similar to previously reported ATG surfactants. 33 The cationic imidazolium ion dominates the surfactants, assembly behavior, both in presence and absence of an oil phase. However, the presence of the carbohydrate enables a significant reduction of the surface tension.…”

Section: Resultsmentioning

confidence: 99%

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Alkyl-imidazolium glycosides: non-ionic—cationic hybrid surfactants from renewable resources

Salman

Tabandeh

Heidelberg

et al. 2015

Carbohydrate Research

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Section: Resultsmentioning

confidence: 99%

“…This approach reflects the previously reported strategy for the synthesis of alkyl triazole glycosides (ATG). 33 …”

Section: Introductionmentioning

confidence: 97%

Alkyl-imidazolium glycosides: non-ionic—cationic hybrid surfactants from renewable resources

Salman

Tabandeh

Heidelberg

et al. 2015

Carbohydrate Research

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“…For each triazole-containing surfactant a single, endothermic peak was observed, as shown in Figure 1. The phase transitions ranged from 122 to 136 °C and, analogous to the structurally related triazole-containing alkyl β-glucopyranosides, 15 increased with increasing chain length (Table 1). The partially fluorinated surfactant 5g melted at 158 °C, which is considerably higher compared to the corresponding hydrocarbon surfactant 5b .…”

Section: Resultsmentioning

confidence: 99%

“…15 This strategy was chosen to yield anomerically pure surfactants, as previous work has suggested the β-alkyl anomers may be more biocompatible. 19-20 Briefly, D-xylose was peracetylated with sodium acetate in acetic anhydride at 100 °C, 21-22 producing 2 as the β-anomer.…”

Section: Resultsmentioning

confidence: 99%

“…Similarly, the increase in the phase transition temperature of the structurally analogous triazole-containing alkyl β-glucopyranosides was less pronounced for surfactants with tetradecyl and hexadecyl tails. 15 The enthalpies associated with the phase transition were calculated from integration of the thermograms and ranged from 26.6 kJ/mol to 45.1 kJ/mol; these values followed the same trend as transition temperature.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, surface properties, and biocompatibility of 1,2,3-triazole-containing alkyl β-d-xylopyranoside surfactants

Oldham

Seelam

Lema

et al. 2013

Carbohydrate Research

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We are interested in the development of surfactants derived from hemicellulosic biomass, as they are potential components in pharmaceuticals, personal care products and other detergents. Such surfactants should exhibit low toxicity in mammalian cells. In this study we synthesized a series of alkyl or fluoroalkyl β-xylopyranosides from azides and an alkyne using the copper-catalyzed azide-alkyne (CuAAC) “Click” reaction in 4 steps from xylose. The purified products were evaluated for both their surfactant properties, and for their biocompatibility. Unlike other carbohydrate-based surfactants, liquid-crystalline behavior was not observed by differential scanning calorimetry. The triazole-containing β-xylopyranosides with short (6 carbons) and long (>12 carbons) chains exhibited no toxicity at concentrations ranging from 1 to 1000 μM. Triazole-containing β-xylopyranosides with 8, 10 or 12 carbons caused toxicity via apoptosis, with CC50 values ranging from 26-890 μM. The two longest chain compounds did form stable monolayers at the air-water interface over a range of temperatures, although a brief transition to an unstable monolayer was observed.

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Transformation of Highly Hydrophobic Triarylphosphines into Amphiphiles via Staudinger Reaction with Hydrophilic Trichlorophenyl Azide

Suzuki,

Akiyama,

Yamashina

et al. 2023

Chemistry A European J

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Owing to its hydrophobic properties and reactivity, triarylphosphines (PAr3) are promising precursors for the development of new amphiphiles. However, an efficient and reliable synthetic method for amphiphiles based on highly hydrophobic PAr3 is still required. Herein, we report a straightforward transformation of highly hydrophobic PAr3 into amphiphiles via the Staudinger reaction. By simply mixing PAr3 and a hydrophilic trichlorophenyl azide containing two hydrophilic chains, amphiphiles bearing a N=P bond (i.e., an azaylide moiety) were quantitatively formed. The obtained azaylide‐based amphiphiles were remarkably water‐soluble, enabling their spontaneous self‐assembly into 2 nm‐sized micelles composed of 4–5 molecules in water with a low critical micelle concentration (up to 0.05 mM or less) due to the effective intermolecular interactions among the hydrophobic surfaces. Although the azaylide moiety is easily hydrolyzed in the presence of water, the azaylide in the amphiphiles displayed notable stability in water even at 60 h, which stems from the LUMO modulation induced by the presence of three electron‐withdrawing chloro groups and two twisted alkoxycarbonyl groups, according to DFT calculations. An amphiphile having a large hydrophobic surface solubilized various hydrophobic organic dyes through efficient intermolecular interactions, resulting in the dyes exhibiting either monomer or excimer emissions in water.

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Alkyl triazole glycosides (ATGs)—A new class of bio-related surfactants

Cited by 31 publications

References 28 publications

Alkyl-imidazolium glycosides: non-ionic—cationic hybrid surfactants from renewable resources

Alkyl-imidazolium glycosides: non-ionic—cationic hybrid surfactants from renewable resources

Synthesis, surface properties, and biocompatibility of 1,2,3-triazole-containing alkyl β-d-xylopyranoside surfactants

Transformation of Highly Hydrophobic Triarylphosphines into Amphiphiles via Staudinger Reaction with Hydrophilic Trichlorophenyl Azide

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