Sugar acrylate‐based polymers as chiral molecularly imprintable hydrogels

Liu, Xiao‐Chuan; Dordick, Jonathan S.

doi:10.1002/(sici)1099-0518(19990601)37:11<1665::aid-pola12>3.3.co;2-v

Cited by 21 publications

(30 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1). The sugar part of the molecule is not effective for selective interaction using conventional noncovalent imprinting routes [23][24][25][26], whereas the aglycon part is common for rutin and quercetin, hence similar shape-selective interaction can be expected for both…”

Section: Evaluation Of Polymer Selectivitymentioning

confidence: 99%

Molecular imprinting of natural flavonoid antioxidants: Application in solid‐phase extraction for the sample pretreatment of natural products prior to HPLC analysis

Theodoridis

Lasáková

Škeříková

et al. 2006

J of Separation Science

View full text Add to dashboard Cite

As shown in the past years, SPE based on molecularly imprinted polymers (MIPs) may provide significant enhancement of selectivity in sample preparation and analyte preconcentration. The objective of this work was the fabrication of MIPs for the specific adsorption of rutin and quercetin. The two flavonoids were used as the template molecules for the preparation of MIP phases in a self-assembly (noncovalent) approach. The produced MIPs were validated with regard to the imprinting efficiency as media for LC and SPE. The retention behavior of several flavonoid compounds was studied using as stationary phases imprinted, control nonimprinted polymers, and commercial silica-based materials. MIPs were applied as materials for the selective SPE and preconcentration of the flavonoids from white and red wine, orange juice, and tea. The collected fractions were analyzed by high-pressure LC. MIP-SPE facilitated specific analyte isolation and effective sample clean-up. The results show that molecularly imprinted SPE can be a useful tool for the simple, selective, and cost-effective pretreatment of samples containing natural antioxidants.

show abstract

Section: Evaluation Of Polymer Selectivitymentioning

confidence: 99%

Molecular imprinting of natural flavonoid antioxidants: Application in solid‐phase extraction for the sample pretreatment of natural products prior to HPLC analysis

Theodoridis

Lasáková

Škeříková

et al. 2006

J of Separation Science

View full text Add to dashboard Cite

show abstract

“…9 Table S1 (available in the Supporting information) summarizes the main results reported in the literature regarding the functionalization of glucose and fructose with polymerizable groups using both the chemical and enzymatic (lipase and protease) routes. In general, the monomer yield/carbohydrate conversion tends to be higher for enzymatic catalysis 12,[23][24][25][26][27][28][29][30][31][32][33][34][35][36] than for the chemical route, 13,[17][18][19][37][38][39][40][41][42] however, high yields in the carbohydrate functionalization can also be achieved using some chemical routes. 13,21,39,42 Moreover, Candida Antarctica lipase B (EC 3.1.1.3), commercially available in a supported form under the name Novozym ® 435, is widely used in the functionalization of carbohydrates in organic media, including the enzymatic-catalyzed carbohydrate (meth)acrylation.…”

Section: Introductionmentioning

confidence: 99%

“…53 A methyl--D-glucopyranoside-6-acrylate-based hydrogel was used as a chiral stationary phase for the resolution of isomers. 30 Studies show that polymers with glucose or fructose moieties are potentially biodegradable and biocompatible. Moreover, carbohydrate moieties in the polymers present the capability of specific interactions with proteins.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic synthesis and structural characterization of methacryloyl‐D‐fructose‐ and methacryloyl‐D‐glucose‐based monomers and poly(methacryloyl‐D‐fructose)‐based hydrogels

Perin

Felisberti

2018

J of Chemical Tech & Biotech

View full text Add to dashboard Cite

BACKGROUND Carbohydrates are important renewable raw materials and their modification by enzymatic reactions with polymerizable groups is of great importance due the possibility of production of polymers with properties for biomedical applications. In this study, D‐fructose‐ and D‐glucose‐based monomers were prepared by enzymatic reactions and structurally characterized. Moreover, hydrogels based on poly(methacryloyl‐D‐fructose) were also prepared and characterized. RESULTS The conversions of 99% and 34% for D‐fructose and D‐glucose, respectively, were achieved using 2,2,2‐trifluoroethyl methacrylate as the methacrylic donor and commercial lipase Novozyme® 435 (EC 3.1.1.3) as enzymatic catalyst in t‐butanol. The molar ratios of D‐fructose and D‐glucose mono‐ and dimethacrylate were 57/43 and 87/13, respectively. These monomers are an isomeric mixture related to the tautomeric equilibrium of the carbohydrates in solution. Methacryloyl‐D‐fructose was polymerized in the presence of a controlled amount of ethyleneglycol dimethacrylate as crosslinker achieving hydrogels with different crosslinking densities which are mechanically stable when subject to compression–decompression cycles and have a high water swelling capability. CONCLUSION The combination of 2,2,2‐trifluoroethylmethacrylate and Novozym® 435 in a heterogeneous media lead to the continuous carbohydrate solubilization and reaction with the formation of carbohydrates‐based monomers. The control of the monomer functionality enables the synthesis of hydrogels with different crosslinking densities that tune their properties. © 2017 Society of Chemical Industry

show abstract

“…28,29 Applications reported in the literature for hydrogels based on carbohydrate are mainly related to drug delivery systems. 12,[30][31][32][33][34][35][36] However, they have also been used as stationary phase in high-performance liquid chromatography 37 and as cell culture media. 38 Crosslinking agents play a key role on the mechanical and physical chemical properties of the hydrogels.…”

Section: Introductionmentioning

confidence: 99%

Macroporous hydrogels based on carbohydrates monomethacrylates and dimethacrylates: singular properties from carbohydrate‐based crosslinkers

Perin

Fonseca

Felisberti

2019

J of Chemical Tech & Biotech

View full text Add to dashboard Cite

BACKGROUND Readily available feedstock and biocompatibility make carbohydrate‐based hydrogels promising materials for biomedical applications. However, carbohydrate‐based crosslinkers are rather underexplored when compared with crosslinkers derived from fossil resources. In this study, novel fully bio‐based hydrogels derived from enzymatically produced d‐fructose and d‐glucose methacrylate monomers were synthesized with different amounts of d‐fructose dimethacrylate crosslinker. RESULTS The use of a carbohydrate‐based crosslinker endows hydrogels with high swelling coefficients, up to 2400%, and superior mechanical resistance (compressive modulus up to 9.5 kPa with a maximum stress up to 50 kPa) compared with conventional crosslinkers based on fossil resources. Hydrogels shape and crosslinking density influences hydrogel morphology, swelling behavior and mechanical resistance. Moreover, hydrogels presented cell viability, biodegradability and hydrolysis‐resistance over a wide range of pH. CONCLUSION The use of a highly hydrophilic crosslinker based on carbohydrate for hydrogels synthesis enables the use of high crosslinker concentration, which improves mechanical properties, however with minor loss of the water swelling capacity, compared with conventional fossil‐based crosslinkers. This is an important advantage over conventional crosslinkers based on fossil resources. Moreover, slab hydrogels hold higher stress under compression–decompression cycles, and present higher resistance to hydrolysis in basic medium due to the thicker pore walls than cylindrical ones. © 2019 Society of Chemical Industry

show abstract

Sugar acrylate‐based polymers as chiral molecularly imprintable hydrogels

Cited by 21 publications

References 0 publications

Molecular imprinting of natural flavonoid antioxidants: Application in solid‐phase extraction for the sample pretreatment of natural products prior to HPLC analysis

Molecular imprinting of natural flavonoid antioxidants: Application in solid‐phase extraction for the sample pretreatment of natural products prior to HPLC analysis

Enzymatic synthesis and structural characterization of methacryloyl‐D‐fructose‐ and methacryloyl‐D‐glucose‐based monomers and poly(methacryloyl‐D‐fructose)‐based hydrogels

Macroporous hydrogels based on carbohydrates monomethacrylates and dimethacrylates: singular properties from carbohydrate‐based crosslinkers

Contact Info

Product

Resources

About