Maja Majerić Elenkov

Maja Majerić Elenkov
Ruđer Bošković Institute | RBI · Division of Organic Chemistry and Biochemistry

About

39
Publications
2,387
Reads
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682
Citations
Citations since 2017
14 Research Items
314 Citations
2017201820192020202120222023020406080
2017201820192020202120222023020406080
2017201820192020202120222023020406080
2017201820192020202120222023020406080
Introduction

Publications

Publications (39)
Article
Biocatalytic modification of fluorinated styrene oxide derivatives: improvement of reaction outcome in terms of reaction yield, selectivity and product optical purity by employing reaction engineering approach.
Article
Ten different fluorinated aromatic epoxides have been tested as potential substrates for halohydrin dehalogenase (HHDH) HheC. The majority of investigated epoxides are useful building blocks in synthetic chemistry applications, with a number of them being polysubstituted. Moderate to high enantioselectivities (ER = 15 → 200) were observed in azidol...
Cover Page
Full-text available
Halohydrin dehalogenase HheC has been studied in the presence of DMSO, the most commonly used co-solvent. A combination of experimental and computational methods was applied to elucidate the behaviour of this homotetrameric enzyme with a focus on its interactions with DMSO molecules. Further details can be found in the Research Article by Z. Brklja...
Preprint
Invited for the cover of this issue are Zlatko Brkljača, Maja Majerić Elenkov and co-workers at the Ruđer Bošković Institute and University of Zagreb. The image depicts the enzyme halohydrin dehalogenase HheC, which is made up of four identical subunits, with marked catalytic residues and volumetric maps of water and DMSO in the active site. Read t...
Preprint
Halohydrin dehalogenase HheC has been studied in the presence of DMSO, the most commonly used co‐solvent. A combination of experimental and computational methods was applied to elucidate the behaviour of this homotetrameric enzyme with a focus on its interactions with DMSO molecules. Further details can be found in the Research Article by Z. Brklja...
Cover Page
Full-text available
The front cover picture was designed by Emina Mehić and Lucija Hok, and illustrated by Josipa Zeba. (© Josipa Zeba. Reproduced with permission.) It depicts the halohydrin dehalogenase‐catalysed conversion of epoxides. Extensive screening of enzymes from group B revealed several highly enantioselective transformations, with HheB showing higher enant...
Article
Halohydrin dehalogenases (HHDHs) possess an unnatural activity of introducing functionalities such as N3, CN, NO2 etc., into a molecule through the ring‐opening reaction of epoxides. The enantioselectivity of HHDHs is substrate‐dependent and not always high enough for synthetic applications. B‐group of HHDHs has been neglected in the past, due to o...
Article
Full-text available
Kinetic resolution of a series of fluorinated styrene oxide derivatives was studied using halohydrin dehalogenase. A mutant HheC-W249P catalysed nucleophilic ring-opening with azide and cyanide ions with excellent enantioselectivity (E-values up to >200), which gives access to various enantiopure β-substituted alcohols and epoxides. It was found th...
Article
At the moment, there are approx. 100 published papers investigating halohydrin dehalogenases from different aspects; enzymology, molecular biology and reactions they can catalyse. Unquestionably, these enzymes are of great importance and hold an immense potential due to the wide spectrum of different compounds that can be synthesized by their actio...
Article
Structure and hydrogen bonding interactions of bioactive oxazolidinones have been studied by means of NMR and vibrational spectroscopies and quantum chemical calculations. We have demonstrated that oxazolidinone derivatives form hydrogen bonds in solution and solid state. Conformational space search has revealed predominant conformations in solutio...
Article
Full-text available
1,2,3-trichloropropane (TCP) being one of the important environmental pollutants, has drawn significant concern due to its highly toxic and carcinogenic effects. In this study, we built a one-pot reaction system in which immobilized haloalkane dehalogenase (DhaA31) and halohydrin dehalognase (HheC) were used to catalyze the recalcitrant TCP to prod...
Article
Biocatalytic ring-opening of epifluorohydrin has been performed by using halohydrin dehalogenase. The enzyme from Mycobacterium sp. GP1 (HheB2) catalysed reaction with high regioselectivity and low enantioselectivity in the presence of different nucleophiles, producing racemic 1-substituted 3-fluoro-2-propanols. No by-products resulting from the ri...
Article
The challenge of chiral chemical production lies in the preparation of chiral building blocks in accordance to green chemistry principles. Thus, the aim of this study was to associate the application of whole-cell biocatalysis (plant cells) and the use of environmentally friendly solvents (NADES) for enantioselective preparation of chiral molecules...
Article
A new procedure for full conformational analyses comprising statistical analysis of molecular dynamics trajectories was developed and applied. The method included coordinate space sampling by molecular dynamics simulations, reduction of dimensionality using tensor decomposition tools, determination of probability distributions in reduced space, and...
Article
Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E = 1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalyse...
Article
An efficient dynamic kinetic resolution protocol using a single enzyme is described. Both the kinetic resolution and substrate racemization are catalyzed by halohydrin dehalogenase from Agrobacterium radiobacter AD1 (HheC). The HheC-catalyzed reaction of epibromohydrin and 2-bromomethyl-2-methyloxirane with sodium cyanate afforded 5-substituted 2-o...
Article
The cyanide-mediated ring opening of epoxides catalyzed by halohydrin dehalogenases yields β-hydroxynitriles that are of high interest for synthetic chemistry. The best studied halohydrin dehalogenase to date is the enzyme from Agrobacterium radiobacter, but this enzyme (HheC) exhibits only low cyanolysis activities. Sequence comparison between a p...
Article
Bioconjugate bidentate ligands 2-10 were obtained by tethering triphenylphosphanecarboxylic acid to amino acid substituted spacers with different flexibility, ranging from a rigid enediyne-based beta-turn inducer to flexible linear aliphatic chains with up to eight carbon atoms. The 21 synthesized ligands revealed up to 81% ee selectivity in rhodiu...
Article
Poly[2-methoxy-5(2′-ethylhexoxy)-p-phenylenevinylene] (MEH-PPV) has been for the first time prepared and fully characterized in enantiopure (R) form. If the polymer molecular weight is sufficiently low, (R)-MEH-PPV assumes a helical supramolecular structure in the solution aggregates, with consequences on the tendency to aggregation and on the fluo...
Article
Full-text available
A novel activity of halohydrin dehalogenases towards spiroepoxides has been found. The enzyme from Arthrobacter sp. (HheA) catalysed highly regioselective azidolysis of spiroepoxides containing 5, 6 and 7-membered cycloalkane rings, while the enzyme from Agrobacterium radiobacter (HheC), besides high regioselectivity, also displayed moderate to hig...
Article
Full-text available
Halohydrin dehalogenase from Agrobacterium radiobacter AD1 (HheC) is a valuable tool in the preparation of R enantiomers of epoxides and β-substituted alcohols. In contrast, the halohydrin dehalogenase from Arthrobacter sp. AD2 (HheA) shows a low S enantioselectivity toward most aromatic substrates. Here, three amino acids (V136, L141, and N178) lo...
Chapter
Alcalase-catalysed Syntheses of Hydrophilic Di- and Tri-peptides in Organic SolventsSelective Alkoxycarbonylation of 1α,25-Dihydroxyvitamin D3 Diol Precursor with Candida antarctica Lipase BThe Use of Lipase Enzymes for the Synthesis of Polymers and Polymer IntermediatesBioconversion of 3-Cyanopyridine into Nicotinic Acid with Gordona terrae NDB116...
Article
Halohydrin dehalogenase from Agrobacterium radiobacter catalyzed the enantioselective ring opening of terminal epoxides with cyanate as a nucleophile, yielding 5-substituted oxazolidinones in high yields and with high enantiopurity (69-98% ee). This is the first example of the biocatalytic conversion of a range of epoxides to the corresponding oxaz...
Article
Full-text available
Easy virtue: Halohydrin dehalogenase is a highly promiscuous enzyme that can catalyze enantioselective epoxide ring opening with at least nine different anionic nucleophiles (see scheme). Its capacity to form carbon–nitrogen, carbon–oxygen, carbon–sulfur, and carbon–carbon bonds makes it possible to use this enzyme for the preparation of a range of...
Article
The cover picture shows a close-up of the promiscuous halide binding site of halohydrin dehalogenase, an enzyme that catalyzes enantioselective epoxide ring opening with a diversity of anionic nucleophiles. Also shown are conversions that give good yields of building blocks for a range of useful, highly enantioenriched, chiral compounds, including...
Article
The halohydrin dehalogenase from Agrobacterium radiobacter AD1 (HheC) catalyzes nucleophilic ring opening of epoxides with cyanide and azide. In the case of 2,2-disubstituted epoxides, this reaction proceeds with excellent enantioselectivity (E values up to >200), which gives, by kinetic resolution, access to various enantiopure epoxides and β-subs...
Article
A sequential kinetic resolution catalyzed by halohydrin dehalogenase was employed for the synthesis of two valuable enantiopure building blocks. Resolution of methyl 4-chloro-3-hydroxybutanoate methylester ((R,S)-2) with use of a Trp249Phe mutant of halohydrin dehalogenase yielded methyl 4-cyano-3-hydroxybutanoate methylester ((S)-4) with 96.8% ee...
Article
Halohydrin dehalogenases (HheA, HheB and HheC) were found to efficiently catalyse a carbon-carbon bond forming reaction between terminal aliphatic epoxides and cyanide, yielding β-hydroxy nitriles. With all three enzymes nucleophilic ring opening of epoxides proceeds with high regioselectivity to the β-carbon atom. Activity, enantioselectivity and...
Article
Halohydrin dehalogenases catalyse the conversion of vicinal halohydrins into their corresponding epoxides, while releasing halide ions. They can be found in several bacteria that use halogenated alcohols or compounds that are degraded via halohydrins as a carbon source for growth. Biochemical and structural studies have shown that halohydrin dehalo...
Article
Immobilized CAL-B catalyzed kinetic resolution of syn-7-bromo-3-(1′-hydroxyethyl)-1-methyl-5-(2′-pyridyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one syn-(±)-2 and its anti-diastereomer (±)-3 were achieved with E-values over 200. Completely enantioselective acetylation of (1′R)-enantiomers in diastereomeric racemates with an opposite configuration at th...
Article
Zn-II and Pd-II complexes of 7-bromo-1,3-dihydro-3-hydroxymethyl-1-methyl-5-(2'-pyridyl)-2H-1,4-benzodiazepin-2-one ((+)-L1), and 3-acetoxymethyl-7-bromo-1,3-dihydro-1-methyl-5-(2'-pyridyl)-2H-1,4-benzodiazepin-2-one ((+/-)-L2) were prepared and determined by spectroscopic studies (IR and H-1 NMR) and X-ray structure analysis. The influence of the...
Article
Enantiomerically pure 7-bromo-1,3-dihydro-3-hydroxymethyl-1-methyl-5-(2′-pyridyl)-2H-1,4-benzodiazepin-2one, (+)-1, affords the dichloro adduct 3, [CuCl2(1)], when treated with a solution of CuCl2·2H2O in ethanol. Complex 3 is isolated as a racemic compound. The replacement of one chlorine atom with DMSO gives complex 4, [CuCl(1-H)(DMSO)]. The C(3)...
Article
Full-text available
Aldol reaction of C(3) carbanion of 7-bromo-5-pyrido-1,4-benzodiazepin-2-one (1) with representative aliphatic and aromatic aldehydes and ketones afforded racemic mixtures syn/anti-7-bromo-3-(1˘-hydroxy-1˘-phenylmethyl)-1-methyl-5-(2'-pyridyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one (2/3), syn/anti-7-bromo-3-(1˘-hydroxy-1˘-phenylmethyl)-1-methyl-5-(...
Article
After recent reports in 1997/98, the low-temperature enhancement of enantioselectivity of the lipase-catalyzed acylations in organic solvents, emerges as a new lab-scale methodology in biocatalysis. The examples of effective production of enantiomerically pure compounds (EPC) at low temperatures, either by kinetic resolution of racemates or by desy...
Article
(R)-2-Ethylhexanol (R-1) is prepared in high optical purity (> 99 % enantiomeric excess, e.e.) by the Pseudomonas sp. lipase-catalyzed acylation of racemic 1 using vinyl laurate as the acylating agent that allows the isolation of (R)-1 by distillation. Nonactivated lauric acid proved to be very reactive, affording (R)-1 with > 99 % e.e., but diffic...

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