Alkylamines are gaining importance due to their proven immunity benefits. Fruits, vegetables, and beverages are important dietary sources for alkylamines. This paper reports for the first time quantitative data on four alkylamines, ethyl-, propyl-, isopropyl-, and sec-butylamines, in commonly consumed fruits and vegetables. A sensitive and selective chromatography method based on derivatization with pentafluorobenzaldehyde and detection by GC-ECD is developed and validated for the analysis of alkylamines in vegetables, fruits, and tea. In vegetables and fruits, the concentrations varied from 100 to 15,000 μg/kg. Propyl- and isopropylamine concentrations were significantly higher compared to other amines. Among all dietary sources, tea had the highest concentration of alkylamines (30-50 mg/kg), with ethylamine as the major component, and is the richest source for alkylamines. The stability of these alkylamines was studied under various cooking conditions, and it was observed that there is loss of alkylamines on cooking.
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Org Lett
January 2025
Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva 8410501, Israel.
A novel class of bis-8-aryl-isoquinoline () bis-alkylamine iron complexes, Fe()(OTf) and Fe()(OTf) ( = dipyrrolidinyl or = ,'-dimethylcyclohexyl-diamine), for asymmetric oxidation reactions is reported. The scalable divergent synthesis of 8-aryl-3-formylisoquinolines (), the key intermediates in preparing these ligands, enables precise structural and electronic tuning around the metal center. The enantioselective epoxidation and hydroxy carbonylation of conjugated alkenes, mediated by the Fe() catalyst with HO as the oxidant, demonstrates the potential of these redox Fe[N] catalysts in inducing face selection in oxygen transfer transformations.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, University of Hawai'i at Ma̅noa, Honolulu, Hawaii 96822, United States.
We present a photocatalytic method for alkylamination of alkenes, enabling efficient C-C and C-N bond formation to construct aza-heterocycles valuable in drug discovery. Using a radical-polar crossover pathway, electron-deficient alkenes are reduced to electrophilic radicals, which react with electron-rich alkenes to form nucleophilic radicals. Oxidation of these intermediates yields carbocations, which are trapped by aza-heteroarenes to afford alkylaminated products.
View Article and Find Full Text PDFJ Org Chem
January 2025
School of Chemistry, State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, Dalian Key Laboratory of Intelligent Chemistry, Dalian University of Technology, Dalian 116024, China.
The mechanistic understanding of how alkylamines impact Ni-metallophotoredox C-N coupling to form diarylamines remains unclear. In this study, 12-alkylamines were evaluated as additives to determine their effects on the synthesis of diarylamines in a flow photochemical system. Notably, -hexylamine demonstrated the most significant promotional effect.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
Dipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, Complesso Universitario di Monserrato, 09042, Monserrato (Cagliari), Italy.
The continuous flow telescoped synthesis of 1,1-cyclopropane aminoketones was achieved by optimizing the photocyclization of 1,2-diketones to 2-hydroxycylobutanones (HCBs) and their reaction with aryl- and alkylamines, tandem condensation C4-C3-ring contraction reaction. With the achieved operational conditions, we were able to obtain a library of cyclopropylamines with good chemical yields, high productivity, and short residence times.
View Article and Find Full Text PDFArch Biochem Biophys
February 2025
Department of Biology and Biotechnology, University of Pavia, Via Ferrata 9, 27100, Pavia, Italy. Electronic address:
Bacterial monoamine oxidases (MAOs) are FAD-dependent proteins catalyzing a relevant reaction for many industrial biocatalytic applications, ranging from production of enantiomerically pure building blocks for pharmaceutical synthesis to biosensors for monitoring food and beverage quality. The thermostable MAO enzyme from Thermoanaerobacterales bacterium (MAO) is about 36 % identical to both putrescine oxidase and human MAOs and can be efficiently produced in Escherichia coli. MAO preferentially acts on n-alkyl monoamines but shows detectable activity also on polyamines and aromatic monoamines.
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