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Tea Pavkov-Keller, Gernot A Strohmeier, Matthias Diepold, Wilco Peeters, Natascha Smeets, Martin Schürmann, Karl Gruber, Helmut Schwab, Kerstin Steiner
Transaminases are useful biocatalysts for the production of amino acids and chiral amines as intermediates for a broad range of drugs and fine chemicals. Here, we describe the discovery and characterisation of new transaminases from microorganisms which were enriched in selective media containing (R)-amines as sole nitrogen source. While most of the candidate proteins were clearly assigned to known subgroups of the fold IV family of PLP-dependent enzymes by sequence analysis and characterisation of their substrate specificity, some of them did not fit to any of these groups...
December 1, 2016: Scientific Reports
Katsuhiro Maeda, Miyuki Maruta, Yuki Sakai, Tomoyuki Ikai, Shigeyoshi Kanoh
A series of optically active poly(diphenylacetylene) derivatives bearing a chiral substituent (poly-2S) or chiral and achiral substituents (poly-(2Sx-co-31-x)) on all of their pendant phenyl rings were synthesized by the reaction of poly(bis(4-carboxyphenyl)acetylene) with (S)-1-phenylethylamine ((S)-2) or benzylamine (3) in the presence of a condensing reagent. Their chiroptical properties and chiral recognition abilities as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) were investigated...
November 7, 2016: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Tao Wang, Haiyan Yang, Ruchen Qiu, Shaohua Huang
Two novel chiral stationary phases (CSPs) were prepared by bonding chiral imidazoliums on the surface of silica gel. The chiral imidazoles were derivatized from chiral amines, 1-phenylethylamine and 1-(1-naphthyl)ethylamine. The obtained CSPs were characterized by Fourier Transform Infrared (FT-IR) spectroscopy and elemental analysis (EA), demonstrating the bonding densities of CSP 1 and CSP 2 were 0.43 mmol g(-1) and 0.40 mmol g(-1), respectively. These two CSPs could be used to availably separate 8 pharmaceuticals, 7 mandelic acid/its derivatives, 2 1-phenylethylamine derivatives, 1 1,1'-bi-2-naphthol, and 1 camphorsulfonic acid in high-performance liquid chromatography (HPLC)...
November 9, 2016: Analytica Chimica Acta
Akifumi Takanabe, Masahito Tanaka, Kohei Johmoto, Hidehiro Uekusa, Tadashi Mori, Hideko Koshima, Toru Asahi
Introducing chirality into photomechanical crystals is beneficial for the diversification of mechanical motion. Measurement of the chiroptical and optical anisotropic properties of chiral crystals is indispensable for evaluating photomechanical crystals. The plate-like crystals of S- and R-enantiomers of photochromic N-3,5-di-tert-butylsalicylidene-1-phenylethylamine in enol form (enol-(S)-1 and enol-(R)-1) caused bending motion with twisting upon ultraviolet (UV) light irradiation, due to shrinkage along the length and width directions of the irradiated surface, based on the optimized crystal structure of the photoisomerized trans-keto-(S)-1...
October 24, 2016: Journal of the American Chemical Society
Markus Schütz, Aude Bouchet, Otto Dopfer
Halogenation of pharmaceutical molecules is a common tool to modify their physiological properties. The geometric, vibrational, and electronic properties of the ortho-fluorinated protonated neurotransmitter 2-phenylethylamine (oF-H(+)PEA) are characterized by infrared photodissociation (IRPD) spectroscopy in the NH stretch range using the messenger technique and dispersion-corrected density functional theory calculations at the B3LYP-D3/aug-cc-pVTZ level to elucidate the drastic effect of site-specific ortho-fluorination...
September 29, 2016: Physical Chemistry Chemical Physics: PCCP
Bernhard Sandig, Michael R Buchmeiser
Enzyme-containing ionic liquids (ILs) were immobilized in cellulose-2.5-acetate microbeads particles embedded in a porous monolithic polyurethane matrix. This bioreactor was used under continuous liquid-liquid conditions by dissolving the substrates in a nonpolar organic phase immiscible with the ILs, thereby creating a biphasic system. Lipases (candida antarctica lipase B, CALB, candida rugosa lipase, CRL) were used to catalyze the enantioselective transesterification of racemic (R,S)-1-phenylethanol with vinyl butyrate and vinyl acetate, the esterification of (+/-)-2-isopropyl-5-methylcyclohexanol with propionic anhydride and the amidation of (R,S)-1-phenylethylamine with ethyl methoxyacetate...
September 21, 2016: ChemSusChem
Rosa Guarcello, Maria De Angelis, Luca Settanni, Sabino Formiglio, Raimondo Gaglio, Fabio Minervini, Giancarlo Moschetti, Marco Gobbetti
: Accumulation of biogenic amines (BAs) in cheese and other foods is a matter of public health concern. This study aimed at identifying enzyme activities responsible for BAs degradation in lactic acid bacteria, which were previously isolated from traditional Sicilian and Apulian cheeses. Selected strains would control the concentration of BAs during cheese manufacture. First, 431 isolates, not showing genes encoding for decarboxylases responsible for BA formation, were selected using PCR-based methods...
September 16, 2016: Applied and Environmental Microbiology
Veronica Gatto, Giulia Tabanelli, Chiara Montanari, Valentina Prodomi, Eleonora Bargossi, Sandra Torriani, Fausto Gardini
Few information is available about the tyraminogenic potential of the species Enterococcus mundtii. In this study, two plant-derived strains of E. mundtii were selected and investigated to better understand the phenotypic behaviour and the genetic mechanisms involved in tyramine accumulation. Both the strains accumulated tyramine from the beginning of exponential phase of growth, independently on the addition of tyrosine to the medium. The strains accumulated also 2-phenylethylamine, although with lower efficiency and in greater extent when tyrosine was not added...
September 14, 2016: Microbial Biotechnology
Carmen Ancín-Azpilicueta, Nerea Jiménez-Moreno, José Antonio Moler, Rodrigo Nieto-Rojo, Henar Urmeneta
Sulphur dioxide (SO2) is an important preservative for wine, but its presence in foods can cause allergies and this has given impetus to the research for alternatives. The aim of this study was to reduce levels of sulfite in wine production using mixtures with lysozyme and dimethyl dicarbonate and examine the influence on levels of volatile and biogenic amines. To do so, vinifications were carried out using lysozyme, dimethyl dicarbonate (DMDC) and mixtures of these with SO2 in different concentrations (25 and 50 mg l(-1))...
October 2016: Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment
Juliet Kinyua, Noelia Negreira, Bram Miserez, Ana Causanilles, Erik Emke, Lies Gremeaux, Pim de Voogt, John Ramsey, Adrian Covaci, Alexander L N van Nuijs
Concerns about new psychoactive substances (NPS) are increasing due to the rising frequency of serious intoxications. Analysis of biological fluids (urine) is necessary to get reliable information about the use of these substances. However, it is a challenging task due to the lack of analytical standards and the dynamic character of the NPS market. In the present work, a qualitative screening of NPS was carried out in 23 pooled urine samples collected from a city center in the UK and festivals in the UK and Belgium...
December 15, 2016: Science of the Total Environment
Fausto Gardini, Yesim Özogul, Giovanna Suzzi, Giulia Tabanelli, Fatih Özogul
Biogenic amines (BAs) are molecules, which can be present in foods and, due to their toxicity, can cause adverse effects on the consumers. BAs are generally produced by microbial decarboxylation of amino acids in food products. The most significant BAs occurring in foods are histamine, tyramine, putrescine, cadaverine, tryptamine, 2-phenylethylamine, spermine, spermidine, and agmatine. The importance of preventing the excessive accumulation of BAs in foods is related to their impact on human health and food quality...
2016: Frontiers in Microbiology
Cecilia Giulivi, Eleonora Napoli, Flora Tassone, Julian Halmai, Randi Hagerman
Premutation carriers have a 55-200 CGG expansion in the fragile X mental retardation 1 (FMR1) gene. Currently, 1.5 million individuals are affected in the United States, and carriers are at risk of developing the late-onset neurodegenerative disorder Fragile X-associated tremor ataxia syndrome (FXTAS). Limited efforts have been made to develop new methods for improved early patient monitoring, treatment response, and disease progression. To this end, plasma metabolomic phenotyping was obtained for 23 premutation carriers and 16 age- and sex-matched controls...
2016: Frontiers in Molecular Neuroscience
U Gianfranco Spizzirri, Nevio Picci, Donatella Restuccia
Biogenic amines (BAs), that is, spermine, spermidine, putrescine, histamine, tyramine, β-phenylethylamine, cadaverine, and serotonin, have been determined in several samples of tea leaves, tea infusions, and tea drinks by LC-UV method after derivatization with dansyl chloride. Different extraction solvents have been tested and TCA 5% showed better analytical performances in terms of linearity, recovery percentages, LOD, LOQ, and repeatability than HCl 0.1 M and HClO4 0.1 M and was finally exploited for the quantitative determination of BAs in all samples...
2016: Journal of Analytical Methods in Chemistry
Honggang Nie, Xianjiang Li, Zhendong Hua, Wei Pan, Yanping Bai, Xiaofang Fu
RATIONALE: With the amounts and types of new psychoactive substances (NPSs) increasing rapidly in recent years, an excellent high-throughput method for the analysis of these compounds is urgently needed. In this article, a rapid screening method and a quantitative analysis method for 11 NPSs are described and compared, respectively. METHOD: A simple direct analysis in real time mass spectrometry (DART-MS) method was developed for the analysis of 11 NPSs including three categories of these substances present on the global market such as four cathinones, one phenylethylamine, and six synthetic cannabinoids...
August 2016: Rapid Communications in Mass Spectrometry: RCM
Sara Eichner, Michelle Maguire, Leticia A Shea, Matthew G Fete
OBJECTIVES: To identify banned and discouraged-use ingredients, such as ephedra, 1,3-dimethylamylamine, and beta-methyl-phenylethylamine, in readily available weight loss dietary supplements within a 10-mile radius of Regis University. METHODS: A list of banned and discouraged-use ingredients was compiled with the use of the Food and Drug Administration (FDA) dietary supplement website which provides information on supplement ingredients that are no longer legal or are advised against owing to adverse event reporting...
September 2016: Journal of the American Pharmacists Association: JAPhA
Muhammad Zahid Khan, Waqas Nawaz
Human trace amines (TAs) are endogenous compounds, previously almost ignored in human pathology for many reasons (difficulty of their measurement in biological fluids, unknown receptors for elusive amines), are now considered to play a significant role in synaptic transmission within the central nervous system (CNS) acting as neuromodulators. The recent discovery of a novel family of G-protein-coupled receptors (GPCRs) that includes individual members that are highly specific for TAs indicates a potential role for TAs as vertebrate neurotransmitters or neuromodulators, although the majority of these GPCRs so far have not been demonstrated to be activated by TAs...
July 14, 2016: Biomedicine & Pharmacotherapy, Biomédecine & Pharmacothérapie
Boris Duffau, Cristian Camargo, Marcelo Kogan, Edwar Fuentes, Bruce Kennedy Cassels
Use of unauthorized synthetic drugs is a serious, forensic, regulatory and public health issue. In this scenario, consumption of drug-impregnated blotters is very frequent. For decades, blotters have been generally impregnated with the potent hallucinogen known as lysergic acid diethylamide (LSD); however, since 2013 blotter stamps with N-2 methoxybenzyl-substituted phenylethylamine hallucinogen designated as "NBOMes" have been seized in Chile. To address this issue with readily accessible laboratory equipment, we have developed and validated a new HPTLC method for the identification and quantitation of 25-C-NBOMe in seized blotters and its confirmation by GC-MS...
August 2016: Journal of Chromatographic Science
Şevket Ata, Mehmet Akyüz, Hasan Çabuk
BACKGROUND: Ion-pair extraction combined with liquid chromatography - tandem mass spectrometry method has been proposed for the determination of biogenic amines in licorice samples. RESULTS: Limit of detection and limit of quantitation for the biogenic amines were 1.4-2.7 and 4.7-9.1 ng mL(-1) , respectively. Relative standard deviations based on five replicate extraction of 100 ng mL(-1) of each biogenic amines were < 4.7 % for intraday and 7.4 % for interday precision...
July 6, 2016: Journal of the Science of Food and Agriculture
Balázs Szemenyei, Ildikó Móczár, Dávid Pál, Ivett Kocsis, Péter Baranyai, Péter Huszthy
Novel enantiopure pyridino-18-crown-6 ether-based sensor molecules containing an anthracene fluorophore unit were synthesized. Their enantiomeric recognition abilities toward the enantiomers of 1-phenylethylamine hydrogen perchlorate (PhEt), 1-(1-naphthyl)ethylamine hydrogen perchlorate (NapEt), phenylglycine methyl ester hydrogen perchlorate (PhgOMe), and phenylalanine methyl ester hydrogen perchlorate (PheOMe) were examined in acetonitrile using fluorescence spectroscopy. The sensor molecules showed appreciable enantiomeric recognition toward the enantiomers of NapEt, PhEt, and PhgOMe...
July 2016: Chirality
Alicja Wzorek, Azusa Sato, Józef Drabowicz, Vadim A Soloshonok
Herein we report a study of the self-disproportionation of enantiomers (SDE) via gravity-driven achiral column chromatography of a series of amides derived from 1-phenylethylamine. We demonstrated that structural and electronic factors of the substituents play an important role in the observed magnitude of the SDE. For the first time, the SDE phenomenon of amides with that of thioamides was compared. We demonstrate that, in sharp contrast to amides, the substitution of the sulphur atom for the oxygen in the acyl group, strongly reduced the observed magnitude of the SDE...
October 7, 2016: Journal of Chromatography. A
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