Cationic curdlan: Synthesis, characterization and application of quaternary ammonium salts of curdlan

Suflet, Dana Mihaela; Popescu, Irina; Pelin, Irina M.; Nicolescu, Alina; Hitruc, Gabriela

doi:10.1016/j.carbpol.2015.01.050

Cited by 39 publications

(13 citation statements)

References 60 publications

(65 reference statements)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…"Click" chemistry has been applied by the Shinkaigroup to incorporate quaternary ammonium moieties into the curdlan backbone; the resultant cationic derivatives demonstrated excellent binding properties with polymeric guest molecules in water. Sufletet al (Suflet, Popescu, Pelin, Nicolescu & Hitruc, 2015) recently reported the synthesis of cationic water-soluble curdlan ammonium salts with DS(ammonium) up to 0.15 by etherification with two types of trialkylammoniumsubstituents. The viscosity of these cationic curdlan derivatives and their interactions with anionic species have been investigated vs. DS and nature of the quaternary substituent, and ionic strength of the aqueous solution.…”

Section: Introductionmentioning

confidence: 99%

Regioselective synthesis of cationic 6-deoxy-6-(N,N,N-trialkylammonio)curdlan derivatives

Zhang

Liu

Edgar

2016

Carbohydrate Polymers

View full text Add to dashboard Cite

Curdlan, a bioactive β-1,3-glucan, is of intense interest for pharmaceutical and biomedical applications. Cationic derivatives of curdlan and other polysaccharides are especially attractive for their potential to interact in controlled fashion with proteins, among many other possible applications, but relatively few methods exist for their synthesis. Herein we report a regioselective method for preparation of cationic, water-soluble 6-(N,N,N-trialkylammonio)-6-deoxycurdlan salts by reaction of 6-bromo-6-deoxycurdlan and its 2,4-O-diesters with trialkylamines. Dimethyl sulfoxide was identified as the optimal solvent for this nucleophilic displacement to produce cationic curdlan derivatives (80 °C, 24h), providing maximum degree of triethylammonium substitution (DS) of 0.89, exclusively at the C-6 position. 6-Bromo-6-deoxycurdlan was also reacted with heterocyclic amines such as pyridine and imidazole, providing ammonium-substituted curdlan derivatives with substantial DS (0.66 and 0.86, respectively). The new combination of regioselective Furuhata bromination and bromine displacement under optimized conditions with tertiary amines provides access to quaternized curdlan derivatives that possess high, permanent positive charge and are readily water-soluble, properties that indicate potential application promise including for mucoadhesion, permeation enhancement, and delivery of genes and anionic drugs. Regioselectivity and DS of those curdlan ammonium derivatives were quantified by means of (1)H NMR, (13)C NMR and FTIR spectroscopic methods and by elemental analysis.

show abstract

Section: Introductionmentioning

confidence: 99%

Regioselective synthesis of cationic 6-deoxy-6-(N,N,N-trialkylammonio)curdlan derivatives

Zhang

Liu

Edgar

2016

Carbohydrate Polymers

View full text Add to dashboard Cite

show abstract

“…From the above, the association ability of Cl − to quaternary ammonium salt cation is evidently relatively strong, whereas that of arsenic anion is relatively weak, which is the main reason for the inhibition of arsenic extraction. A larger anion radius corresponds to a smaller charge, and a lower degree of hydration of the aqueous solution corresponds to a greater advantage in extraction (Suflet et al, 2015;Chauhan and Kaur, 2017). It can be inferred that the association ability of HAsOS 2− 2 is between CO 2− 3 and AsO 3− 4 , and the extraction ability of arsenic may be improved if the Cl − quaternary ammonium salt is transformed into the CO 2− 3 type.…”

Section: Resultsmentioning

confidence: 99%

Study on Extraction Separation of Thioarsenite Acid in Alkaline Solution by CO32--Type Tri-n-Octylmethyl-Ammonium Chloride

et al. 2021

View full text Add to dashboard Cite

To overcome the problem of arsenic separation and enrichment from an alkaline leaching solution in arsenic-containing dust, a CO32--type tri-n-octylmethyl-ammonium chloride (TOMAC) method for extracting thioarsenite is proposed in this paper. Considering an alkaline leaching solution as the research object, after vulcanization pretreatment, TOMAC transformation and organic phase saturated extraction capacity were measured, and the extraction mechanism was preliminarily studied. First, Cl−-type quaternary ammonium salt was effectively transformed to HCO3--type by treating organic phase with saturated NaHCO3five times. TOMAC was effectively transformed from HCO3- to CO32- type by alkaline washing with 1.0 mol/l NaOH solution; this washing was repeated thrice. Thereafter, the effects of organic phase composition, phase ratio, extraction time, and temperature on the extraction and separation of arsenic were investigated. The results show that under the conditions of 30% CO32--type TOMAC + 15% sec-octanol + 55% sulfonated kerosene, VO/VA = 1/1, and 5 min extraction at room temperature, the single-stage extraction rate of AsIII is 85.2%. The AsIII concentration in raffinate can be reduced to less than 1.33 × 10−3 mol/l by four-stage countercurrent extraction, and the extraction rate of AsIII can exceed 98.4%.

show abstract

“… Cai et al (2019) , Cho et al (2015) , Huang et al (2019b) , Lee et al (2020) , Liu and Edgar (2015b) , Lu et al (2019) , Ni et al (2019) , Rogge and Stevens (2004) , Singh et al (2019) , Suflet et al (2015) .…”

Section: Uncited Referencesmentioning

confidence: 99%

Potential applications of hydrophobically modified inulin as an active ingredient in functional foods and drugs - A review

Usman

Zhang

Patil

et al. 2021

Carbohydrate Polymers

View full text Add to dashboard Cite

show abstract

Cationic curdlan: Synthesis, characterization and application of quaternary ammonium salts of curdlan

Cited by 39 publications

References 60 publications

Regioselective synthesis of cationic 6-deoxy-6-(N,N,N-trialkylammonio)curdlan derivatives

Regioselective synthesis of cationic 6-deoxy-6-(N,N,N-trialkylammonio)curdlan derivatives

Study on Extraction Separation of Thioarsenite Acid in Alkaline Solution by CO32--Type Tri-n-Octylmethyl-Ammonium Chloride

Potential applications of hydrophobically modified inulin as an active ingredient in functional foods and drugs - A review

Contact Info

Product

Resources

About