4.6 Article

Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 23, Pages 8171-8177

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob06251d

Keywords

-

Funding

  1. Generalitat de Cataluna [2009SGR871]
  2. MICINN [AGL2009-13452-C02-01]

Ask authors/readers for more resources

Both enantiomers of several phenylethylamines, structurally related to amphetamine, have been prepared in good yields and excellent enantiomeric purity by enzymatic kinetic resolution using CAL-B and ethyl methoxyacetate as the acyl donor. In the case of the 4-hydroxyderivative of amphetamine (compound 4i), the S enantiomer racemized possibly in a dynamic kinetic resolution (DKR) under the enzymatic conditions used.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.6
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Behavioral Sciences

Factors influencing aversive learning in the oriental fruit fly, Bactrocera dorsalis

J. L. Liu, H. L. Chen, X. Y. Chen, R. K. Cui, A. Guerrero, X. N. Zeng

JOURNAL OF COMPARATIVE PHYSIOLOGY A-NEUROETHOLOGY SENSORY NEURAL AND BEHAVIORAL PHYSIOLOGY (2017)

Article Chemistry, Organic

New and Convenient Chemoenzymatic Syntheses of (S)-2-Hydroxy-3-octanone, the Major Pheromone Component of Xylotrechus spp., and Its R-Enantiomer

Marc Puigmarti, Maria Pilar Bosch, Josep Coll, Angel Guerrero

SYNTHESIS-STUTTGART (2017)

Review Biochemistry & Molecular Biology

A2A Adenosine Receptor Agonists and their Potential Therapeutic Applications. An Update

Angel Guerrero

CURRENT MEDICINAL CHEMISTRY (2018)

Article Gastroenterology & Hepatology

Clinical Feasibility of Large Gastrotomy Closure Using a Flexible Tissue Glue Based on N-Butyl-2-Cyanoacrylate: Experimental Study in Pigs

Francisco Espin Alvarez, Anna M. Rodriguez Rivero, Jordi Navines Lopez, Elena Diaz Celorio, Jordi Tarasco Palomares, Luis Felipe del Castillo Riestra, Iva Borisova, Jaime Fernandez-Llamazares, Pau Turon Dols, Joan Francesc Julian Ibanez

JOURNAL OF GASTROINTESTINAL SURGERY (2019)

Article Materials Science, Biomaterials

Loading of Antibiotic into Biocoated Hydroxyapatite Nanoparticles: Smart Antitumor Platforms with Regulated Release

Manuel Rivas, Luis J. del Valle, Anna M. Rodriguez-Rivero, Pau Turon, Jordi Puiggali, Carlos Aleman

ACS BIOMATERIALS SCIENCE & ENGINEERING (2018)

Article Agriculture, Multidisciplinary

Enantioselective Synthesis and Activity of All Diastereoisomers of (E)-Phytal, a Pheromone Component of the Moroccan Locust, Dociostaurus maroccanus

Angel Guerrero, Victoria Elena Ramos, Sergio Lopez, Jose Maria Alvarez, Aroa Dominguez, Maria Milagro Coca-Abia, Maria Pilar Bosch, Carmen Quero

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Biominerals Formed by DNA and Calcium Oxalate or Hydroxyapatite: A Comparative Study

Guillem Revilla-Lopez, Anna M. Rodriguez-Rivero, Luis J. del Valle, Jordi Puiggali, Pau Turon, Carlos Aleman

LANGMUIR (2019)

Article Entomology

Influence of Age, Host Plant and Mating Status in Pheromone Production and New Insights on Perception Plasticity in Tuta Absoluta

Aroa Dominguez, Sergio Lopez, Ana Bernabe, Angel Guerrero, Carmen Quero

INSECTS (2019)

Article Biochemical Research Methods

Development and validation of a mass spectrometry binding assay for mGlu5 receptor

Maria Ricart-Ortega, Alice E. Berizzi, Juanlo Catena, Fanny Malhaire, Lourdes Munoz, Carmen Serra, Guillaume Lebon, Cyril Goudet, Amadeu Llebaria

ANALYTICAL AND BIOANALYTICAL CHEMISTRY (2020)

Article Multidisciplinary Sciences

Inhibitory effect of thymol on pheromone-mediated attraction in two pest moth species

Sergio Lopez, Aroa Dominguez, Angel Guerrero, Carmen Quero

Summary: Plant essential oils, especially thyme oil and its major constituent thymol, were evaluated for their potential as disruptants of pheromone-mediated communication and mating behavior in major pest moths. Results showed that both thyme oil and thymol altered antennal response in males and interrupted pheromone-mediated attraction, indicating their potential as pest control tools. Further research is needed to explore the specific mechanisms and effects of thyme oil and thymol on mating disruption in these species.

SCIENTIFIC REPORTS (2021)

Article Oncology

Unravelling the Encapsulation of DNA and Other Biomolecules in HAp Microcalcifications of Human Breast Cancer Tissues by Raman Imaging

Monica Marro, Anna M. Rodriguez-Rivero, Cuauhtemoc Araujo-Andrade, Maria Teresa Fernandez-Figueras, Laia Perez-Roca, Eva Castella, Jordi Navines, Antonio Mariscal, Joan Francesc Julian, Pau Turon, Pablo Loza-Alvarez

Summary: In this study, the biochemical composition of breast cancer microcalcifications was investigated, revealing the natural adsorption and encapsulation of DNA within hydroxyapatite formations in breast cancer tissue. Other relevant biomolecules such as lipids, proteins, cytochrome C, and polysaccharides were also found to be encapsulated in these calcifications, representing an important breakthrough in understanding the role of hydroxyapatite in malignant tissues.

CANCERS (2021)

Review Entomology

Latest Developments in Insect Sex Pheromone Research and Its Application in Agricultural Pest Management

Syed Arif Hussain Rizvi, Justin George, Gadi V. P. Reddy, Xinnian Zeng, Angel Guerrero

Summary: Insect pheromones, particularly sex pheromones, have been highly successful in controlling low density pest populations and reducing pest populations with minimal impact on their natural enemies. Mass trapping and mating disruption strategies using sex pheromones have significantly decreased the use of conventional insecticides, providing sustainable and eco-friendly pest management in agricultural crops. Recent interdisciplinary research has greatly advanced our understanding of pheromone perception mechanisms and their practical applications in agricultural pest management.

INSECTS (2021)

Article Biochemistry & Molecular Biology

S-Methyl-L-Ergothioneine to L-Ergothioneine Ratio in Urine Is a Marker of Cystine Lithiasis in a Cystinuria Mouse Model

Miguel Lopez de Heredia, Lourdes Munoz, Ciriaco Carru, Salvatore Sotgia, Angelo Zinellu, Carmen Serra, Amadeu Llebaria, Yukio Kato, Virginia Nunes

Summary: Cystinuria is a rare inherited disorder characterized by hyperexcretion of certain amino acids, leading to cystine stone formation in the urinary tract. Study analyzing levels of S-methyl-L-ergothioneine in urine showed potential as a biomarker for discriminating between different cystinuria phenotypes based on age, gender, and stone formation characteristics. Improved management of cystinuria patients could be achieved through monitoring this urinary biomarker.

ANTIOXIDANTS (2021)

Article Multidisciplinary Sciences

Caged-carvedilol as a new tool for visible-light photopharmacology of β-adrenoceptors in native tissues

Anna Duran-Corbera, Joan Font, Melissa Faria, Eva Prats, Marta Consegal, Juanlo Catena, Lourdes Munoz, Demetrio Raldua, Antonio Rodriguez-Sinovas, Amadeu Llebaria, Xavier Rovira

Summary: This study presents a new photopharmacological tool that allows the control of adrenoceptor activity through light-induced release. The tool effectively modulates various physiological systems, providing potential for the development of precise therapies in the future.

ISCIENCE (2022)

Article Chemistry, Medicinal

Mechanistic Insights into Light-Driven Allosteric Control of GPCR Biological Activity

Maria Ricart-Ortega, Alice E. Berizzi, Vanessa Pereira, Fanny Malhaire, Juanlo Catena, Joan Font, Xavier Gomez-Santacana, Lourdes Munoz, Charleine Zussy, Carmen Serra, Xavier Rovira, Cyril Goudet, Amadeu Llebaria

ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE (2020)

Article Chemistry, Organic

Catalyst-free photo-induced aerobic radical synthesis of lactams from N-alkenyl trichloroacetamides in 2-methyltetrahydrofuran as the radical initiator under violet light

Faiza Diaba, Gisela Trenchs

Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

Article Chemistry, Organic

Synthesis of mixed phosphorotrithioates via thiol coupling with bis(diisopropylamino)chlorophosphine and sulphenyl chloride

Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed

Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

Article Chemistry, Organic

Catalyst-free assembly of a polyfunctionalized 1,2,4-triazole-fused N-heterocycle, 6-acylated pyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine

Hyunjin Oh, Ikyon Kim

Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

Article Chemistry, Organic

Synthesis of sulfinamides via photocatalytic alkylation or arylation of sulfinylamine

Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li

Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

Article Chemistry, Organic

Two distinct protocols for the synthesis of unsymmetrical 3,4-disubstituted maleimides based on transition-metal catalysts

Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst

Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

Article Chemistry, Organic

Conversion of amino-terephthalonitriles to multi-substituted single benzene fluorophores with utility in bioimaging

Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar

Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)

Review Chemistry, Organic

Microbial alcohol dehydrogenases: recent developments and applications in asymmetric synthesis

Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan

Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.

ORGANIC & BIOMOLECULAR CHEMISTRY (2024)