Search results for: Jesús Joglar

Items from 1 to 20 out of 37 results

article

Expanding Synthetic Applications of Δ¹‐Piperidine‐2‐carboxylate/Δ¹‐pyrroline‐2‐carboxylate Reductase from Pseudomonas syringae (DpkA_Psyrin). Biocatalytic Asymmetric Synthesis of (S,E)‐2‐hydroxy‐4‐arylbut‐3‐enoic Acid Derivatives

Carlos J. Moreno, Samantha Gittings, Dieter Schollmeyer, Jesús Joglar, more

Advanced Synthesis & Catalysis > 366 > 4 > 990 - 1000

Chiral 2‐hydroxy‐4‐arylbut‐3‐enoic acid derivatives are important precursors for the synthesis of angiotensin converting enzyme (ACE) inhibitors, such as enalapril, lisinopril, cilapril or benazepril. In this work, we take advantage of the unexplored promiscuous ketoreductase activity of Δ¹‐piperidine‐2‐carboxylate/Δ¹‐pyrroline‐2‐carboxylate reductase from Pseudomonas syringae pv. tomato DSM 50315...

article

Chemoenzymatic Production of Enantiocomplementary 2‐Substituted 3‐Hydroxycarboxylic Acids from l‐α‐Amino Acids

Mathias Pickl, Roser Marín‐Valls, Jesús Joglar, Jordi Bujons, more

Advanced Synthesis & Catalysis > 363 > 11 > 2866 - 2876

A two‐enzyme cascade reaction plus in situ oxidative decarboxylation for the transformation of readily available canonical and non‐canonical l‐α‐amino acids into 2‐substituted 3‐hydroxycarboxylic acid derivatives is described. The biocatalytic cascade consisted of an oxidative deamination of l‐α‐amino acids by an l‐α‐amino acid deaminase from Cosenzaea myxofaciens, rendering 2‐oxoacid intermediates,...

article

Aldolase‐Catalyzed Asymmetric Synthesis of N‐Heterocycles by Addition of Simple Aliphatic Nucleophiles to Aminoaldehydes

Raquel Roldán, Karel Hernández, Jesús Joglar, Jordi Bujons, more

Advanced Synthesis & Catalysis > 361 > 11 > 2673 - 2687

Nitrogen heterocycles are structural motifs found in many bioactive natural products and of utmost importance in pharmaceutical drug development. In this work, a stereoselective synthesis of functionalized N‐heterocycles was accomplished in two steps, comprising the biocatalytic aldol addition of ethanal and simple aliphatic ketones such as propanone, butanone, 3‐pentanone, cyclobutanone, and cyclopentanone...

article

Titelbild: Nucleophile Promiscuity of Engineered Class II Pyruvate Aldolase YfaU from E. Coli (Angew. Chem. 14/2018)

Karel Hernández, Jesús Joglar, Jordi Bujons, Teodor Parella, more

Angewandte Chemie > 130 > 14 > 3581 - 3581

Strukturgeleitetes Protein‐Engineering … … der Klasse‐II‐Pyruvat‐Aldolase YfaU aus E. coli wird von P. Clapés und Mitarbeitern in ihrer Zuschrift auf S. 3645 als direkter Weg zu chiralen Bausteinen sowie zu Prolin‐ und Pyrrolizidin‐α‐aminosäure‐Derivaten beschrieben. Das Bild vergleicht YfaU mit einem Räderwerk, das ein Nukleophil und ein Elektrophil zur C‐C‐Kupplung zusammenbringt. Die vorausgehende...

article

Nucleophile Promiscuity of Engineered Class II Pyruvate Aldolase YfaU from E. Coli

Karel Hernández, Jesús Joglar, Jordi Bujons, Teodor Parella, more

Angewandte Chemie > 130 > 14 > 3645 - 3649

Pyruvate‐dependent aldolases exhibit a stringent selectivity for pyruvate, limiting application of their synthetic potential, which is a drawback shared with other existing aldolases. Structure‐guided rational protein engineering rendered a 2‐keto‐3‐deoxy‐l‐rhamnonate aldolase variant, fused with a maltose‐binding protein (MBP‐YfaU W23V/L216A), capable of efficiently converting larger pyruvate analogues,...

article

Cover Picture: Nucleophile Promiscuity of Engineered Class II Pyruvate Aldolase YfaU from E. Coli (Angew. Chem. Int. Ed. 14/2018)

Karel Hernández, Jesús Joglar, Jordi Bujons, Teodor Parella, more

Angewandte Chemie International Edition > 57 > 14 > 3521 - 3521

Structure‐guided protein engineering of the class II pyruvate aldolase YfaU from E. coli is described. In their Communication on page 3583 ff., P. Clapés and co‐workers report the resulting straightforward access to chiral building blocks and proline and pyrrolizidine α‐amino acid derivatives. The picture shows how YfaU works like a timing gear to bring together the nucleophile and electrophile to...

article

Nucleophile Promiscuity of Engineered Class II Pyruvate Aldolase YfaU from E. Coli

Karel Hernández, Jesús Joglar, Jordi Bujons, Teodor Parella, more

Angewandte Chemie International Edition > 57 > 14 > 3583 - 3587

article

Ionization and collision induced dissociation of steroid bisglucuronides

Argitxu Esquivel, Xavier Matabosch, Aristotelis Kotronoulas, Georgina Balcells, more

Journal of Mass Spectrometry > 52 > 11 > 759 - 769

Studies on steroid metabolism are of utmost importance to improve the detection capabilities of anabolic androgenic steroids (AASs) misuse in sports drug testing. In humans, glucuronoconjugates are the most abundant phase II metabolites of AAS. Bisglucuronidation is a reaction where two separated functional groups on the same molecule are conjugated with glucuronic acid. These metabolites have not...

article

2‐Keto‐3‐Deoxy‐l‐Rhamnonate Aldolase (YfaU) as Catalyst in Aldol Additions of Pyruvate to Amino Aldehyde Derivatives

Karel Hernández, Ariadna Gómez, Jesús Joglar, Jordi Bujons, more

Advanced Synthesis & Catalysis > 359 > 12 > 2090 - 2100

4‐Hydroxy‐2‐keto acid derivatives are versatile building blocks for the synthesis of amino acids, hydroxy carboxylic acids and chiral aldehydes. Pyruvate aldolases are privileged catalysts for a straightforward access to this class of keto acid compounds. In this work, a Class II pyruvate aldolase from Escherichia coli K‐12, 2‐keto‐3‐deoxy‐l‐rhamnonate aldolase (YfaU), was evaluated for the synthesis...

article

Intramolecular Benzoin Reaction Catalyzed by Benzaldehyde Lyase from Pseudomonas Fluorescens Biovar I

Karel Hernández, Teodor Parella, Giovanna Petrillo, Isabel Usón, more

Angewandte Chemie International Edition > 56 > 19 > 5304 - 5307

Intramolecular benzoin reactions catalyzed by benzaldehyde lyase from Pseudomonas fluorescens biovar I (BAL) are reported. The structure of the substrates envisaged for this reaction consists of two benzaldehyde derivatives linked by an alkyl chain. The structural requirements needed to achieve the intramolecular carbon–carbon bond reaction catalyzed by BAL were established. Thus, a linker consisting...

article

Intramolecular Benzoin Reaction Catalyzed by Benzaldehyde Lyase from Pseudomonas Fluorescens Biovar I

Karel Hernández, Teodor Parella, Giovanna Petrillo, Isabel Usón, more

Angewandte Chemie > 129 > 19 > 5388 - 5391

article

Evaluation of two glucuronides resistant to enzymatic hydrolysis as markers of testosterone oral administration

Aristotelis Kotronoulas, Alex Gomez-Gomez, Jordi Segura, Rosa Ventura, more

The Journal of Steroid Biochemistry and Molecular Biology > 2017 > 165 > PB > 212-218

Testosterone (T) has traditionally been the most commonly reported doping agent by doping control laboratories. The screening of T misuse is performed by the quantification of six endogenous androgenic steroids and the ratio T/E included in the Athlete Biological Passport (ABP). The inclusion of additional metabolites can improve the screening capabilities of ABP. In this study, the potential of 3α-glucuronide-6β-hydroxyandrosterone...

article

Detection and characterization of clostebol sulfate metabolites in Caucasian population

Georgina Balcells, Oscar J. Pozo, Lorena Garrostas, Argitxu Esquivel, more

Journal of Chromatography B > 2016 > 1022 > C > 54-63

Anabolic androgenic steroids (AAS) are synthetic testosterone derivatives which undergo extensive metabolism in man. Differences in the excretion of phase II metabolites are strongly associated with inter-individual and inter-ethnic variations. Sulfate metabolites have been described as long-term metabolites for some AAS. Clostebol is the 4-chloro derivative of testosterone and the aim of the present...

article

Ultra high performance liquid chromatography tandem mass spectrometric detection of glucuronides resistant to enzymatic hydrolysis: Implications to doping control analysis

Aristotelis Kotronoulas, Josep Marcos, Jordi Segura, Rosa Ventura, more

Analytica Chimica Acta > 2015 > 895 > C > 35-44

Controversial results have been reported in the literature regarding the behavior of two testosterone (T) metabolites (3α-glucuronide-6β-hydroxyandrosterone and 3α-glucuronide-6β-hydroxyetiocholanolone) excreted after T administration. Due to their potential as biomarkers of T misuse, a UHPLC–MS/MS method for the direct quantification of these glucuronides was developed and validated. In addition,...

article

Structure‐Guided Engineering of D‐Fructose‐6‐Phosphate Aldolase for Improved Acceptor Tolerance in Biocatalytic Aldol Additions

Anna Soler, Mariana L. Gutiérrez, Jordi Bujons, Teodor Parella, more

Advanced Synthesis & Catalysis > 357 > 8 > 1787 - 1807

A structure‐guided redesign of D‐fructose‐6‐phosphate aldolase from Escherichia coli (FSA) was devised for improving the acceptor tolerance towards α‐substituted and conformationally constrained aldehydes. FSA A129S/R134X/A165G/S166G and L107Y/A129G/R134X/A165G/S166G variants, where X was R, V, P, or S, were the most suited biocatalysts for dihydroxyacetone, hydroxyacetone and glycolaldehyde additions...

article

Screening for anabolic steroids in sports: Analytical strategy based on the detection of phase I and phase II intact urinary metabolites by liquid chromatography tandem mass spectrometry

Georgina Balcells, Oscar J. Pozo, Argitxu Esquivel, Aristotelis Kotronoulas, more

Journal of Chromatography A > 2015 > 1389 > Complete > 65-75

In order to improve the detection capabilities of anabolic androgenic steroids (AAS) in sports, a liquid chromatography–tandem mass spectrometry (LC–MS/MS) screening method for the simultaneous detection of AAS phase I and phase II intact urinary metabolites (glucuronides and sulfates) was developed.A total of 36 metabolites (7 unconjugated; 19 glucuronides and 10 sulfates) corresponding to 15 of...

article

Engineered L‐Serine Hydroxymethyltransferase from Streptococcus thermophilus for the Synthesis of α,α‐Dialkyl‐α‐Amino Acids

Karel Hernandez, Igor Zelen, Giovanna Petrillo, Isabel Usón, more

Angewandte Chemie > 127 > 10 > 3056 - 3060

α,α‐Disubstituted α‐amino acids are central to biotechnological and biomedical chemical processes for their own sake and as substructures of biologically active molecules for diverse biomedical applications. Structurally, these compounds contain a quaternary stereocenter, which is particularly challenging for stereoselective synthesis. The pyridoxal‐5′‐phosphate (PLP)‐dependent L‐serine hydroxymethyltransferase...

article

Engineered L‐Serine Hydroxymethyltransferase from Streptococcus thermophilus for the Synthesis of α,α‐Dialkyl‐α‐Amino Acids

Karel Hernandez, Igor Zelen, Giovanna Petrillo, Isabel Usón, more

Angewandte Chemie International Edition > 54 > 10 > 3013 - 3017

article

Expedient Synthesis of C‐Aryl Carbohydrates by Consecutive Biocatalytic Benzoin and Aldol Reactions

Karel Hernández, Teodor Parella, Jesús Joglar, Jordi Bujons, more

Chemistry – A European Journal > 21 > 8 > 3335 - 3346

The introduction of aromatic residues connected by a CC bond into the non‐reducing end of carbohydrates is highly significant for the development of innovative structures with improved binding affinity and selectivity (e.g., Caril‐sLex). In this work, an expedient asymmetric “de novo” synthetic route to new aryl carbohydrate derivatives based on two sequential stereoselectively biocatalytic carboligation...

article

Engineering the Donor Selectivity of D‐Fructose‐6‐Phosphate Aldolase for Biocatalytic Asymmetric Cross‐Aldol Additions of Glycolaldehyde

Anna Szekrenyi, Anna Soler, Xavier Garrabou, Christine Guérard‐Hélaine, more

Chemistry – A European Journal > 20 > 39 > 12572 - 12583

D‐Fructose‐6‐phosphate aldolase (FSA) is a unique catalyst for asymmetric cross‐aldol additions of glycolaldehyde. A combination of a structure‐guided approach of saturation mutagenesis, site‐directed mutagenesis, and computational modeling was applied to construct a set of FSA variants that improved the catalytic efficiency towards glycolaldehyde dimerization up to 1800‐fold. A combination of mutations...

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INFONA - science communication portal

Search results for: Jesús Joglar

Expanding Synthetic Applications of Δ¹‐Piperidine‐2‐carboxylate/Δ¹‐pyrroline‐2‐carboxylate Reductase from Pseudomonas syringae (DpkA_Psyrin). Biocatalytic Asymmetric Synthesis of (S,E)‐2‐hydroxy‐4‐arylbut‐3‐enoic Acid Derivatives

Chemoenzymatic Production of Enantiocomplementary 2‐Substituted 3‐Hydroxycarboxylic Acids from l‐α‐Amino Acids

Aldolase‐Catalyzed Asymmetric Synthesis of N‐Heterocycles by Addition of Simple Aliphatic Nucleophiles to Aminoaldehydes

Titelbild: Nucleophile Promiscuity of Engineered Class II Pyruvate Aldolase YfaU from E. Coli (Angew. Chem. 14/2018)

Nucleophile Promiscuity of Engineered Class II Pyruvate Aldolase YfaU from E. Coli

Cover Picture: Nucleophile Promiscuity of Engineered Class II Pyruvate Aldolase YfaU from E. Coli (Angew. Chem. Int. Ed. 14/2018)

Nucleophile Promiscuity of Engineered Class II Pyruvate Aldolase YfaU from E. Coli

Ionization and collision induced dissociation of steroid bisglucuronides

2‐Keto‐3‐Deoxy‐l‐Rhamnonate Aldolase (YfaU) as Catalyst in Aldol Additions of Pyruvate to Amino Aldehyde Derivatives

Intramolecular Benzoin Reaction Catalyzed by Benzaldehyde Lyase from Pseudomonas Fluorescens Biovar I

Intramolecular Benzoin Reaction Catalyzed by Benzaldehyde Lyase from Pseudomonas Fluorescens Biovar I

Evaluation of two glucuronides resistant to enzymatic hydrolysis as markers of testosterone oral administration

Detection and characterization of clostebol sulfate metabolites in Caucasian population

Ultra high performance liquid chromatography tandem mass spectrometric detection of glucuronides resistant to enzymatic hydrolysis: Implications to doping control analysis

Structure‐Guided Engineering of D‐Fructose‐6‐Phosphate Aldolase for Improved Acceptor Tolerance in Biocatalytic Aldol Additions

Screening for anabolic steroids in sports: Analytical strategy based on the detection of phase I and phase II intact urinary metabolites by liquid chromatography tandem mass spectrometry

Engineered L‐Serine Hydroxymethyltransferase from Streptococcus thermophilus for the Synthesis of α,α‐Dialkyl‐α‐Amino Acids

Engineered L‐Serine Hydroxymethyltransferase from Streptococcus thermophilus for the Synthesis of α,α‐Dialkyl‐α‐Amino Acids

Expedient Synthesis of C‐Aryl Carbohydrates by Consecutive Biocatalytic Benzoin and Aldol Reactions

Engineering the Donor Selectivity of D‐Fructose‐6‐Phosphate Aldolase for Biocatalytic Asymmetric Cross‐Aldol Additions of Glycolaldehyde

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