Lipase-catalyzed synthesis and characterization of copolymers from ethyl acrylate as the only monomer starting material

Rustoy, Eduardo Miguel; Sato, Yasuto; Nonami, Hiroshi; Erra‐Balsells, Rosa; Baldessari, Alicia

doi:10.1016/j.polymer.2007.01.040

Cited by 25 publications

(11 citation statements)

References 24 publications

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“…Numerous examples pertain to the stereoselective synthesis of chiral intermediates for the production of various pharmaceuticals and plant-protecting agents (Andualema & Gessesse, 2012;Baldessari, 2012;Naik et al, 2010;Sharma et al, 2011;Song et al, 2008). Moreover, there are many cases of promiscuous reactions catalyzed by CAL-B, including aldol reactions, Michael additions, vinyl polymerization, and even oxidations (Branneby et al, 2004;Carboni-Oerlemans et al, 2006;Carlqvist et al, 2003;Carlqvist et al, 2005;Hult & Berglund, 2007;Madalińska et al, 2012;Rustoy et al, 2007;Sharma et al, 2009;Svedendahl et al, 2005;Wu et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

Crystal and molecular structure of hexagonal form of lipase B from Candida antarctica.

Strzelczyk¹,

Bujacz²,

Kiełbasiński³

et al. 2015

Acta Biochim Pol

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During crystallization screenings of commercially available hydrolytic enzymes, the new, hexagonal crystal form of CAL-B, has been discovered and hereby reported. The NAG molecules, which were closing the glycosylation site in the orthorhombic form, in hexagonal structure make the glycosylation site open. It is unknown whether the opening and closing of the glycosylation site by the 'lid' NAG molecules, could be related to the opening and closing of the active center of the enzyme upon substrate binding and product release.

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Section: Introductionmentioning

confidence: 99%

Crystal and molecular structure of hexagonal form of lipase B from Candida antarctica.

Strzelczyk¹,

Bujacz²,

Kiełbasiński³

et al. 2015

Acta Biochim Pol

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“…The low dispersity is also a characteristic of enzymatic polymerizations. In previous work we obtained nearly monodisperse products by CAL B‐catalyzed polymerization reactions …”

Section: Discussionmentioning

confidence: 99%

“…Moreover, lipases are able to catalyze polymerization reactions without involving acyl substitution at all, e.g. acrylic polymerization and aza‐Michael addition . Lipase‐catalyzed polymerizations enable polymer preparation under smooth reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic synthesis of novel N -(2-hydroxyethyl)-β-peptoid oligomer derivatives and application to porous polycaprolactone films

et al. 2013

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Poly[N-(2-hydroxyethyl)-β-propylamide] oligomer is synthesized using a simple enzymatic procedure involving Candida antarctica lipase B. This novel compound is obtained by a green and chemoselective method from economic reactants in good yield. The β-peptoid oligomer is characterized by spectroscopic methods showing low molecular weight and low dispersity. Two derivatives of the β-peptoid oligomer are prepared by acetylation and by grafting polycaprolactone by ring opening polymerization from the pendant hydroxyl groups. These products are blended with polycaprolactone to make films by solvent casting. The inclusion of the acyl derivatives of the β-peptoid to polycaprolactone affects the morphology of the film yielding microstructured and nanostructured patterns.

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“…When the other neutral maltoses, thiosaccharides, and fructans were studied, CHCA.nHo always performed as a quite good matrix in and 1679]). Furthermore, spectra for MbCD, DMbCD, and TMbCD are also included in Supporting Information (Figures S3ii-iv); they showed to be complex mixtures with the formula (CH3) [9][10][11][12][13][14][15][16] bCD, (CH3) [13][14][15][16][17][18] bCD, and (CH3) 20-21 bCD, respectively. Best results were obtained with the IL CHCA.nHo as matrix.…”

Section: Neutral Carbohydratesmentioning

confidence: 99%

norHarmane containing ionic liquid matrices for low molecular weight MALDI‐MS carbohydrate analysis: The perfect couple with α‐cyano‐4‐hydroxycinnamic acid

2019

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Cinnamic acid derivatives, particularly α‐cyano‐4‐hydroxycinnamic acid (E‐α‐cyano‐4‐hydroxycinnamic acid or (E)‐2‐cyano‐3‐(4‐hydroxyphenyl)prop‐2‐enoate; CHCA), have been extensively used especially for protein and peptide analysis. Together with the introduction of ionic liquid MALDI matrix (ILM) started the study of applications of IL prepared with CHCA and a counter organic base (ie, aliphatic amines) in which CHCA moiety is the chromophore responsible of UV‐laser absorption. Despite the extensive studies of norharmane (9H‐pyrido[3,4‐b]indole; nHo) applications as matrix and its peculiar basic properties in the ground and electronic excited state, nHo containing ILM was never tested in MALDI‐MS experiments. This pyrido‐indole compound was introduced as MALDI matrix 22 years ago for different applications including low molecular weight (LMW) carbohydrates (neutral, acidic, and basic carbohydrates). These facts encouraged us to use it as a base, for the first time, for ILM preparation. As a rational design of new IL MALDI matrices, E‐α‐cyanocinnamic acid.nHo and E‐cinnamic acid.nHo were prepared and their properties as matrices studied. Their performance was compared with that of (a) the corresponding IL prepared with butylamine as basic component, (b) the corresponding crystalline E‐α‐cyanocinnamic and E‐cinnamic acid, and (c) the classical crystalline matrices (2,5‐dihydroxybenzoic acid, DHB; nHo) used in the analysis of neutral/sulfated carbohydrates. The IL DHB.nHo was tested, too. Herein, we demonstrate the outstanding performance for the IL CHCA.nHo for LMW carbohydrate in positive and negative ion mode (linear and reflectron modes). Sulfated oligosaccharides were detected in negative ion mode, and although the dissociation of sulfate groups was not completely suppressed the relative intensity (RI) of [M − Na]− peak was quite high. Additionally, to better understand the quite different performance of each IL tested as matrix, the physical and morphological properties in solid state were studied (optical image; MS image).

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Lipase-catalyzed synthesis and characterization of copolymers from ethyl acrylate as the only monomer starting material

Cited by 25 publications

References 24 publications

Crystal and molecular structure of hexagonal form of lipase B from Candida antarctica.

Crystal and molecular structure of hexagonal form of lipase B from Candida antarctica.

Chemoenzymatic synthesis of novel N -(2-hydroxyethyl)-β-peptoid oligomer derivatives and application to porous polycaprolactone films

norHarmane containing ionic liquid matrices for low molecular weight MALDI‐MS carbohydrate analysis: The perfect couple with α‐cyano‐4‐hydroxycinnamic acid

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