Biocatalytic esterification of β-methylglucoside for synthesis of biocompatible sugar-containing vinyl esters

Kim, J

doi:10.1016/j.cej.2003.09.001

Cited by 22 publications

(16 citation statements)

References 20 publications

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“…The overall effect of temperature is also affected by other factors such as the amount and type of substrate used, and presence of water in the reaction. Also, substrate molar ratio is an important factor to obtain the highest product yield and the lowest side reaction (Kim et al, 2004). Temperature, substrate molar ratio (SR), and Lipozyme TLIM had a negative effect whereas Novozym 435 had a positive effect on stearic acid incorporation.…”

Section: Effect Of Parametersmentioning

confidence: 95%

Enzymatic synthesis of trans-free structured margarine fat analogs with high stearate soybean oil and palm stearin and their characterization

Pande

Akoh

2013

LWT - Food Science and Technology

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Section: Effect Of Parametersmentioning

confidence: 95%

Enzymatic synthesis of trans-free structured margarine fat analogs with high stearate soybean oil and palm stearin and their characterization

Pande

Akoh

2013

LWT - Food Science and Technology

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“…Kim and co‐workers reported the synthesis of vinyl sugar ester by the transesterification of β‐methyl glucoside with vinyl methacrylate or vinyl acrylate in both homogeneous and heterogeneous media catalyzed by Novozym® 435. In both media, the conversion of the glucoside was 100%.…”

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

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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

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“…1 H NMR (δ in ppm) of MGAA : 5.96, 6.12 (1, CHCH 2 ), 5.61, 5.84 (2, CHCH 2 ), 6.3, 6.43 (3, CHCH 2 ). MGMAA : 1.98 (1, CH 2 CCH 3 ), 5.58, 5.64 (2, CH 2 CCH 3 ), 6.11, 6.24 (3, CH 2 CCH 3 ), all splitted 13, 14, 17. Structures and carbon numbers of MGAA and MGMAA for 13 C NMR spectra are shown in Figure 3.…”

Section: Resultsmentioning

confidence: 99%

“…13 C NMR/CDCl 3 (δ in ppm) of MGAA : 59.90 (OCH 3 , 1), 63.79 (C‐7), 69.70 (C‐6), 73.17 (C‐4), 75.82 (C‐5), 75.99 (C‐3), 103.31 (C‐2), 128.13 (CCH 2 , 9), 131.76 (CCH 2 , 10), 166.34 (CO, 8). MGMAA : 18.31 (CH 3 , 9), 56.96 (OCH 3 , 1), 64.37 (C‐7), 70.58 (C‐6), 73.37 (C‐4), 73.75 (C‐5), 76.32 (C‐3), 103.40 (C‐2), 126.46 (CCH 2 , 10), 135.96 (CCH 2 , 11), 167.81 (CO, 8) 13, 14…”

Section: Resultsmentioning

confidence: 99%

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Chemoenzymatic synthesis of sugar‐containing biocompatible hydrogels: Crosslinked poly(β‐methylglucoside acrylate) and poly(β‐methylglucoside methacrylate)

Park

Haam

Lee

et al. 2004

J Biomedical Materials Res

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Sugar-containing biocompatible hydrogels were synthesized chemoenzymatically by the following two steps: 1. lipase-catalyzed esterification of beta-methylglucoside with acrylic acid/methacrylic acid/vinyl acrylate/vinyl methacrylate in solvent as well as solvent-free process for the formation of sugar-containing monomers; and 2. polymerization process by free-radical polymerization with and without a crosslinker, ethylene glycol dimethacrylate (EGDMA). The solvent-free process resulted in an initial reaction rate approximately 1.5-2 times faster than that of the solvent process along with a complete consumption of beta-methylglucoside during the alcoholysis. The presence of pendant vinyl groups in beta-methylglucoside acrylate (MGAA) and beta-methylglucoside methacrylate (MGMAA) was confirmed by (1)H/(13)C NMR analysis, whereas the successful polymerization with the consumption of the vinyl groups was confirmed by Fourier transform infrared spectroscopy and (13)C NMR spectra. The surfaces of both poly(MGAA) and poly(MGMAA) were analyzed using scanning electron microscopy. The increased contents of EGDMA resulted in a higher tensile strength as well as a reduced swelling ratio of poly(MGAA) and poly(MGMAA). The swelling exponents were within the range of 0.53 and 0.98. In vitro cytotoxicity tests by MTT assay exhibited >90% cell viability in the poly(MGAA) and poly(MGMAA) without EGDMA, whereas a significantly decreased cell viability was observed for those with EGDMA.

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Biocatalytic esterification of β-methylglucoside for synthesis of biocompatible sugar-containing vinyl esters

Cited by 22 publications

References 20 publications

Enzymatic synthesis of trans-free structured margarine fat analogs with high stearate soybean oil and palm stearin and their characterization

Enzymatic synthesis of trans-free structured margarine fat analogs with high stearate soybean oil and palm stearin and their characterization

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

Chemoenzymatic synthesis of sugar‐containing biocompatible hydrogels: Crosslinked poly(β‐methylglucoside acrylate) and poly(β‐methylglucoside methacrylate)

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