Self-Association of Poly[2-(β-D-glucosyloxy)ethyl Acrylate] in Water

Liang, Yu-Zeng; Li, Zi‐Chen; Li, Fu‐Mian

doi:10.1006/jcis.1999.6644

Cited by 23 publications

(29 citation statements)

References 27 publications

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“…Yet, since the number average contour length of the glycopolymer ( R max ) is 20 nm and its R g in water is 6.7 nm (Table 3), the profile height of 1.5–3 nm measured by AFM is incompatible with a side‐by‐side lamellar arrangement of polymer chains and does not support the observation of deflated vesicles, whose thickness would be at least twice that of the membrane. Further study is needed on this particular aspect, but it is interesting to note that our results closely resemble those reported by Liang et al72 for the self‐association of poly[2‐(β‐D‐glucosyloxy)ethyl acrylate] (a homoglycopolymer) in aqueous solution. In that case, masking the hydrophobic polymer backbone from the surrounding water was suggested to be the driving force for self‐association.…”

Section: Resultssupporting

confidence: 87%

Aqueous RAFT Polymerization ofN‐Acryloylmorpholine, Synthesis of an ABA Triblock Glycopolymer and Study of its Self‐Association Behavior

Albertin

Wolnik

Ghadban

et al. 2012

Macro Chemistry & Physics

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The RAFT polymerization of N -acryloylmorpholine with a symmetric trithiocarbonate was investigated in homogeneous aqueous solution. The effects of temperature and of a high magnetic fi eld were examined and RAFT experiments were compared with the corresponding conventional radical polymerizations. For all temperatures tested, the molar mass of the polymer increased linearly with conversion and closely matched the theoretical value. Molar mass dispersities were in the range 1.05-1.16 and the presence of a magnetic fi eld had little effect on the rate of RAFT polymerizations, although the latter were systematically slower than the corresponding conventional processes. A uniform ABA triblock glycopolymer was prepared, which formed unilamellar polymersomes with a diameter of 380 nm in 91% (v/v) THF/ water mixture. inducing their colloidal association by addition of a selective water-miscible organic solvent. Conversely, polyNAMderived hydrophilic-hydrophobic block copolymers could be prepared that dissolve in water-miscible organic solvents but form aggregates upon dilution with water.The reversible addition-fragmentation chain transfer (RAFT) polymerization of N -acryloylmorpholine (NAM) in organic solvent has already been reported in the literature, mainly by M-T. Charreyre and her collaborators, and a number of different chain transfer agents (CTAs) have been tested (Scheme 1 ). In particular, Favier et al. [2][3][4] showed that a good control of the molecular weight is achieved with tertiary alkyl dithiobenzoates 1-2 in 1,4-dioxane at 90 ° C, whereas at 60 ° C the same CTAs lead to molar masses signifi cantly higher than those predicted by theory. Similar results were observed with CTA 3 . At the same time, D'Agosto et al. [ 5 ] tested 2-[(2-phenylethanethioyl)sulfanyl]propanoic acid 4 and 2-[(phenylcarbonothioyl)sulfanyl]propanoic acid 5 in 1,4-dioxane at described the RAFT copolymerization of NAM with N -acryloxysuccinimide, [ 10 , 11 ] and various carbohydrate-functionalized acrylamides. [12][13][14] Other laboratories have been studying the RAFT polymerization of NAM, although less systematically. For instance, Eberhardt and Theato [ 15 ] chain extended poly(pentafl uorphenyl methacrylate)dithiobenzoate macro-CTAs 9 with NAM in 1,4-dioxane at 90 ° C and obtained amphiphilic block copolymers with Ð = 1.30-1.39. Jo et al. [ 1 ] used 5 under the same conditions to synthesize a poly(NAM) macro-CTA that was then chain extended with N -acryloylpiperidine or N -acryloylazocane to afford amphiphilic block copolymers of different composition. A study of their self-association in water demonstrated that all copolymers formed micellelike spherical aggregates independently of their composition. Li et al. [ 16 ] synthesized poly(methylacrylate)-bpoly( N -acryloyloxysuccinimide-co -Nacryloylmorpholine) by chain extending S -poly(methylacrylate)-S ′-(1-dodecyl) trithiocarbonate 10 with a mixture of N -acryloyloxysuccinimide and NAM in toluene at 60 ° C. The resulting polymer had Ð = 1.18 and was used in the preparation o...

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Section: Resultssupporting

confidence: 87%

Aqueous RAFT Polymerization ofN‐Acryloylmorpholine, Synthesis of an ABA Triblock Glycopolymer and Study of its Self‐Association Behavior

Albertin

Wolnik

Ghadban

et al. 2012

Macro Chemistry & Physics

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“…However, it was reported that some of them tend to self-assemble, likely due to the combination of hydrophobic interactions and cooperative hydrogen bonding originating from the polymer backbone and the saccharide moieties, respectively. 49,50 As determined by DLS and confirmed by cryo-TEM (Fig. 3 and Table 1) the pTreA 40 and pSucA 42 glycopolymers were also prone to forming such self-assemblies in aqueous solution.…”

Section: Polymer Chemistry Papermentioning

confidence: 75%

Structurally analogous trehalose and sucrose glycopolymers – comparative characterization and evaluation of their effects on insulin fibrillation

et al. 2022

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“…As a result of the enzyme‐catalyzed transglycosidation, the product was anomerically pure and selectively functionalized at the C1 position. Alternatively, similar monomers could be synthesized by conventional chemistry11b or microwave‐assisted reaction,16 but the synthesis would require at least two more reaction steps for protection and deprotection of the hydroxyl groups.…”

Section: Resultsmentioning

confidence: 99%

Enzyme‐Catalyzed Synthesis of Saccharide Acrylate Monomers from Nonedible Biomass

Kloosterman

Brouwer

Loos³

2014

Chemistry An Asian Journal

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Various cellulase preparations were found to catalyze the transglycosidation between cotton linters and 2-hydroxyethyl acrylate. The conversion and enzyme activity were found to be optimal in reaction mixtures that contained 5 vol % of the acrylate. The structures of the products were revealed by using TLC and (1) H and (13) C NMR spectroscopy. The enzyme-catalyzed reaction resulted in two products. The minor product originated from transglycosidation to hemicellulose and was found to be 2-(β-xylosyloxy)-ethyl acrylate. The major product was identified as 2-(β-glucosyloxy)-ethyl acrylate and the yield of the product was 5 wt % based on the amount of consumed cellulose. Glycosidation products with oligosaccharide moieties could not be detected in the reaction mixture. This result can be explained by the hydrolytic activities of the used cellulase preparation. Cellulase from Trichoderma reesei was found to possess, in addition to endoglucanase activity, cellobiosidase and β-glucosidase activities. Five other cellulase preparations from different origins were tested as well for catalysis of oligosaccharide acrylate synthesis. For most cellulase preparations the major transglycosidation product appeared to be 2-(β-glucosyloxy)-ethyl acrylate. Nevertheless, the endo-β-(1,4)-glucanase from Trichoderma longibrachiatum was found to catalyze the synthesis of 2-(β-cellobiosyloxy)-ethyl acrylate. Unlike the other cellulase preparations, endo-β-(1,4)-glucanase from T. longibrachiatum showed no detectable β-glucosidase activity and therefore oligosaccharide acrylate monomers were not further hydrolyzed into the monosaccharide acrylate 2-(β-glucosyloxy)-ethyl acrylate.

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Self-Association of Poly[2-(β-D-glucosyloxy)ethyl Acrylate] in Water

Cited by 23 publications

References 27 publications

Aqueous RAFT Polymerization ofN‐Acryloylmorpholine, Synthesis of an ABA Triblock Glycopolymer and Study of its Self‐Association Behavior

Aqueous RAFT Polymerization ofN‐Acryloylmorpholine, Synthesis of an ABA Triblock Glycopolymer and Study of its Self‐Association Behavior

Structurally analogous trehalose and sucrose glycopolymers – comparative characterization and evaluation of their effects on insulin fibrillation

Enzyme‐Catalyzed Synthesis of Saccharide Acrylate Monomers from Nonedible Biomass

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