Biocatalytic synthesis of new copolymers from 3-hydroxybutyric acid and a carbohydrate lactone

Kakasi-Zsurka, Sándor; Todea, Anamaria; But, Andrada; Paul, Cristina; Boeriu, Carmen G.; Davidescu, Corneliu Mircea; Nagy, Lajos; Kuki, Ákos; Kéki, Sándor; Péter, Fráncisc

doi:10.1016/j.molcatb.2011.03.004

Cited by 21 publications

(12 citation statements)

References 26 publications

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“…However, important differences concerning the product composition were observed. The relative content of linear (LC) and cyclic (CC) copolymers was higher than previously found in the reaction products obtained from 3HBA and GL (Kakasi-Zsurka et al, 2011). The formation of linear (LH) and cyclic (CH) homopolymers could not be avoided, possibly due to the ECL excess employed, particularly in the solvent-less systems, where ECL had the role of reaction medium as well.…”

Section: Influence Of the Reaction Medium And The Water Contentmentioning

confidence: 63%

“…Recently, our group firstly demonstrated the ability of lipase to use GL, together with 3-hydroxybutyric acid, as substrate for copolymer formation (Kakasi-Zsurka et al, 2011). In the present study, ECL was used as co-monomer, anticipating higher cycle reactivity due to the higher polymerization degree of PCL synthesized by lipases, compared to polyhydroxybutyrate (Mee van der et al, 2006).…”

Section: Lipase-catalyzed Copolymerization Of Ecl and δ-Gluconolactonmentioning

confidence: 79%

“…MALDI-TOF MS analysis of products was carried out using Bruker BIFLEX III matrix assisted laser desorption ionization time-oflight mass spectrometry (Bruker Daltonik GmbH, Germany) at an acceleration voltage of 20 kV using 2,5-dihydroxybenzoic acid as matrix. Sample preparation, weight average (M w ) and number average (M n ) molecular numbers, and the product relative content were determined as described elsewhere (Kakasi-Zsurka et al, 2011). Within every MALDI-TOF spectrum, we estimated the relative composition of the reaction product assuming that the ionization efficiency was not significantly different for the oligomeric species present in the mixture.…”

Section: Methodsmentioning

confidence: 99%

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Biocatalytic synthesis of δ-gluconolactone and ε-caprolactone copolymers.

et al. 2014

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The biodegradability and biocompatibility properties of ε-caprolactone homopolymers place it as a valuable raw material, particularly for controlled drug delivery and tissue engineering applications. However, the usefulness of such materials is limited by their low hydrophilicity and slow biodegradation rate. In order to improve polycaprolactone properties and functionalities, copolymerization of ε-caprolactone with δ-gluconolactone was investigated. Since enzymatic reactions involving sugars are usually hindered by the low solubility of these compounds in common organic solvents, finding the best reaction medium was a major objective of this research. The optimal copolymerization conditions were set up by using different organic media (solvent and solvents mixtures), as well as solvent free systems that are able to dissolve (completely or partially) sugars, and are nontoxic for enzymes. Native and immobilized lipases by different immobilization techniques from Candida antarctica B and Thermomyces lanuginosus have been used as biocatalyst at 80°C. Although the main copolymer amount was synthesized in DMSO:t-BuOH (20:80) medium, the highest polymerization degrees, up to 16 for the copolymer product, were achieved in solventless conditions. The products, cyclic and linear polyesters, have been characterized by FT-IR and MALDI-TOF MS analysis. The reaction product analysis revealed the formation of cyclic products that could be the major impediment of further increase of the chain length.

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Section: Influence Of the Reaction Medium And The Water Contentmentioning

confidence: 63%

Section: Lipase-catalyzed Copolymerization Of Ecl and δ-Gluconolactonmentioning

confidence: 79%

Section: Methodsmentioning

confidence: 99%

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Biocatalytic synthesis of δ-gluconolactone and ε-caprolactone copolymers.

et al. 2014

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“…( Kakasi-Zsurka et al, 2011) Core-shell nanoassemblies based on -CD-containing block copolymer and poly( -benzyl L-aspartate) TOF (dithranol) Hydrophobic molecules resided preferably in the cores of assemblies Cyclodextrin-centred star polymers TOF Synthesized from cyclodextrin-(SH) 7 by a combination of thiol-ene click and ring opening polymerization -CD plus poly(N-Pr iacrylamide)and poly(N,Ndi-Me-acrylamide TOF (CHCA) Three-arm star copolymer. Thermally reversible hydrogel Diblock copolymers of regioselectively methylated cellulose and unmodified cello-oligosaccharides TOF Synthesis of diblock methylcellulose derivatives with regioselective functionalization patterns (Nakagawa et al, 2011b) Fibrous cellulose TOF Use of cross-linked mutant endoglucanase II to produce fibrils rather than plate-like crystals (Nakamura et al, 2011a) Glyconanocapsules TOF Click chemistry with di-triazolo-sucrose (Roux et al, 2012) Glyco-poly(2-oxazoline)s TOF (DCTB) Synthesis, cloud point tuning, and lectin (Kempe et al, 2011) binding Glycosylated poly-(naphthalene/phenylene) copolymer R-TOF (DHB) Synthesis and characterization of an amphiphilic blue-light-emitting polymer Helical polypeptide-grafted cyclodextrin bioconjugates TOF Synthesis, secondary and self-assembly structures, and inclusion complex with guest compounds Hyperbranched polymers from poly(N-isopropylacrylamide) containing one adamantyl and twocyclodextrins TOF (CHCA) cationexchange resin to improve ionization Spontaneously forms supramolecular thermoresponsive hyperbranched polymers via molecular recognition between adamantane and -cyclodextrin moieties Cyclodextrin-based TOF Six -cyclodextrins, PEG axle, end caps …”

Section: Tof (Dhb)mentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

Harvey

2015

Mass Spectrometry Reviews

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This review is the seventh update of the original article published in 1999 on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2012. General aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, and fragmentation are covered in the first part of the review and applications to various structural types constitute the remainder. The main groups of compound are oligo- and poly-saccharides, glycoproteins, glycolipids, glycosides, and biopharmaceuticals. Much of this material is presented in tabular form. Also discussed are medical and industrial applications of the technique, studies of enzyme reactions, and applications to chemical synthesis. © 2015 Wiley Periodicals, Inc. Mass Spec Rev 36:255-422, 2017.

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“…They are used as catalysts in biotransformations for the production of pharmaceuticals, agrochemicals, pesticides, insecticides etc. [1][2][3]. Their application in biotechnology is of special importance due to their exceptional properties like enantioselectivity, regioselectivity and chemoselectivity [4].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of factors influencing the enantioselective enzymatic esterification of lactic acid in ionic liquid

Findrik

Németh

Gubicza

et al. 2011

Bioprocess Biosyst Eng

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In this paper esterification of ethanol and lactic acid catalyzed by Candida antarctica B (Novozyme 435) in ionic liquid (Cyphos 104) was studied. The influence of different variables on lipase enantioselectivity and lactic acid conversion was investigated. The variables investigated were ionic liquid mass/lipase mass ratio, water content, alcohol excess and temperature. Using the Design Expert software 2(3) factorial experimental plan (two levels, three factors) was performed to ascertain the effect of selected variables and their interactions on the ethyl lactate enantiomeric excess and lactic acid conversion. The results of the experiments and statistical processing suggest that temperature and alcohol excess have the highest effect on the ethyl lactate enantiomeric excess, while temperature and water content have the highest influence on the lactic acid conversion. The statistical mathematical model developed on the basis of the experimental data showed that the highest enantiomeric excess achieved in the investigated variable range is 34.3%, and the highest conversion is 63.8% at the initial conditions of water content at 8%; 11-fold molar excess of alcohol and temperature at 30 °C.

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Biocatalytic synthesis of new copolymers from 3-hydroxybutyric acid and a carbohydrate lactone

Cited by 21 publications

References 26 publications

Biocatalytic synthesis of δ-gluconolactone and ε-caprolactone copolymers.

Biocatalytic synthesis of δ-gluconolactone and ε-caprolactone copolymers.

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

Evaluation of factors influencing the enantioselective enzymatic esterification of lactic acid in ionic liquid

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