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An aggregation-induced emission (AIE) active chiral compound, dipyridine diphenyl-substituted butadiene derivative (R-TPCD-PEA), was synthesized by introducing a chiral phenylethylamine. It shows excellent AIE activity and efficient luminescent performance. Optical activity analysis reveals that it has an obvious aggregation-induced circular dichroism (AICD) characteristic. And it is a potential candidate for enantiomer recognition.

Synthetic control over chirality and function is the crowning achievement for metal-organic frameworks, but the same level of control has not been achieved for covalent organic frameworks (COFs). Here we demonstrate chiral COFs (CCOFs) can be crystallized from achiral organic precursors by chiral catalytic induction. A total of nine two-dimensional CCOFs are solvothermally prepared by imine condensations of the C 3 -symmetric 1,3,5-triformylphloroglucinol (Tp) with diamine or triamine linkers in the presence of catalytic amount of ( R )- or ( S )-1-phenylethylamine. Homochirality of these CCOFs results from chiral catalyst-induced immobilization of threefold-symmetric tris( N -salicylideneamine) cores with a propeller-like conformation of one single handedness during crystallization. The CCOF-TpTab showed high enantioselectivity toward chiral carbohydrates in fluorescence quenching and, after postsynthetic modification of enaminone groups located in chiral channels with Cu(II) ions, it can also be utilized as a heterogeneous catalyst for the asymmetric Henry reaction of nitroalkane with aldehydes. Controlling chirality and function in metal organic frameworks has been an achievement, but very difficult to carry out in covalent organic frameworks. Here the authors show chiral covalent organic frameworks that are crystallized from achiral precursors by chiral catalytic induction.

Single crystalline perovskites exhibit high optical absorption, long carrier lifetime, large carrier mobility, low trap-state-density and high defect tolerance. Unfortunately, all single crystalline perovskites attained so far are limited to bulk single crystals and small area wafers. As such, it is impossible to design highly demanded flexible single-crystalline electronics and wearable devices including displays, touch sensing devices, transistors, etc. Herein we report a method of induced peripheral crystallization to prepare large area flexible single-crystalline membrane (SCM) of phenylethylamine lead iodide (C 6 H 5 C 2 H 4 NH 3 ) 2 PbI 4 with area exceeding 2500 mm 2 and thinness as little as 0.6 μm. The ultrathin flexible SCM exhibits ultralow defect density, superior uniformity and long-term stability. Using the superior ultrathin membrane, a series of flexible photosensors were designed and fabricated to exhibit very high external quantum efficiency of 26530%, responsivity of 98.17 A W −1 and detectivity as much as 1.62 × 10 15 cm Hz 1/2 W −1 (Jones). Hybrid halide perovskite single crystals show excellent optoelectronic properties but their small size and large thickness limit their application. Herein Liu et al. grow large area ultrathin flexible crystalline membrane of layered perovskite and demonstrate high detectivity in the flexible photosensors.

Essential foods as part of a daily meal may include numerous kinds of biogenic amines (BAs) at various concentrations. BAs have a variety of toxicological effects on human health and have been linked to multiple outbreaks of foodborne disease. BAs also are known to cause cancer based on their ability to react with nitrite salts, resulting in the production of carcinogenic organic compounds (nitrosamines). Ingestion of large quantities of BAs in food causes toxicological effects and health disorders, including psychoactive, vasoactive, and hypertensive effects and respiratory, gastrointestinal, cardiovascular, and neurological disorders. The toxicity of BAs is linked closely to the BAs histamine and tyramine. Other amines, such as phenylethylamine, putrescine, and cadaverine, are important because they can increase the negative effects of histamine. The key method for reducing BA concentrations and thus foodborne illness is management of the bacterial load in foods. Basic good handling and hygiene practices should be used to control the formation of histamine and other BAs and reduce the toxicity histamine and tyramine. A better understanding of BAs is essential to enhance food safety and quality. This review also includes a discussion of the public health implications of BAs in foods.

Up to 50–70% of patients with liver cirrhosis develop hepatic encephalopathy (HE), which is closely related to gut microbiota dysbiosis, with an unclear mechanism. Here, by constructing gut–brain modules to assess bacterial neurotoxins from metagenomic datasets, we found that phenylalanine decarboxylase (PDC) genes, mainly from Ruminococcus gnavus , increased approximately tenfold in patients with cirrhosis and higher in patients with HE. Cirrhotic, not healthy, mice colonized with R. gnavus showed brain phenylethylamine (PEA) accumulation, along with memory impairment, symmetrical tremors and cortex-specific neuron loss, typically found in patients with HE. This accumulation of PEA was primarily driven by decreased monoamine oxidase-B activity in both the liver and serum due to cirrhosis. Targeting PDC or PEA reversed the neurological symptoms induced by R. gnavus . Furthermore, fecal microbiota transplantation from patients with HE to germ-free cirrhotic mice replicated these symptoms and further corroborated the efficacy of targeting PDC or PEA. Clinically, high baseline PEA levels were linked to a sevenfold increased risk of HE after intrahepatic portosystemic shunt procedures. Our findings expand the understanding of the gut–liver–brain axis and identify a promising therapeutic and predictive target for HE. The gut microbiota bacterium Ruminococcus gnavus is implicated in the development of cirrhotic liver encephalopathy through the production of neurotoxins.

Trace amine-associated receptor 1 (TAAR1), the founding member of a nine-member family of trace amine receptors, is responsible for recognizing a range of biogenic amines in the brain, including the endogenous β-phenylethylamine (β-PEA) 1 as well as methamphetamine 2 , an abused substance that has posed a severe threat to human health and society 3 . Given its unique physiological role in the brain, TAAR1 is also an emerging target for a range of neurological disorders including schizophrenia, depression and drug addiction 2 , 4 , 5 . Here we report structures of human TAAR1–G-protein complexes bound to methamphetamine and β-PEA as well as complexes bound to RO5256390, a TAAR1-selective agonist, and SEP-363856, a clinical-stage dual agonist for TAAR1 and serotonin receptor 5-HT 1A R (refs. 6 , 7 ). Together with systematic mutagenesis and functional studies, the structures reveal the molecular basis of methamphetamine recognition and underlying mechanisms of ligand selectivity and polypharmacology between TAAR1 and other monoamine receptors. We identify a lid-like extracellular loop 2 helix/loop structure and a hydrogen-bonding network in the ligand-binding pockets, which may contribute to the ligand recognition in TAAR1. These findings shed light on the ligand recognition mode and activation mechanism for TAAR1 and should guide the development of next-generation therapeutics for drug addiction and various neurological disorders. We report on the structures of the TAAR1–G-protein complex when bound to methamphetamine and other amines.

Odorants are detected as smell in the nasal epithelium of mammals by two G-protein-coupled receptor families, the odorant receptors and the trace amine-associated receptors 1 , 2 (TAARs). TAARs emerged following the divergence of jawed and jawless fish, and comprise a large monophyletic family of receptors that recognize volatile amine odorants to elicit both intraspecific and interspecific innate behaviours such as attraction and aversion 3 – 5 . Here we report cryo-electron microscopy structures of mouse TAAR9 (mTAAR9) and mTAAR9–G s or mTAAR9–G olf trimers in complex with β-phenylethylamine, N , N -dimethylcyclohexylamine or spermidine. The mTAAR9 structures contain a deep and tight ligand-binding pocket decorated with a conserved D 3.32 W 6.48 Y 7.43 motif, which is essential for amine odorant recognition. In the mTAAR9 structure, a unique disulfide bond connecting the N terminus to ECL2 is required for agonist-induced receptor activation. We identify key structural motifs of TAAR family members for detecting monoamines and polyamines and the shared sequence of different TAAR members that are responsible for recognition of the same odour chemical. We elucidate the molecular basis of mTAAR9 coupling to G s and G olf by structural characterization and mutational analysis. Collectively, our results provide a structural basis for odorant detection, receptor activation and G olf coupling of an amine olfactory receptor. Cryo-electron microscopy structures of mouse trace amine-associated receptor 9 reveals structural motifs involved in odorant ligand recognition, including a unique disulfide bond linking the N terminus to extracellular loop 2.

Phenylethylamine (PEA) derivatives are integral to pharmaceutical and material synthesis. The introduction of fluorinated functional groups can induce modifications in the molecular properties. Consequently, it is essential to examine the effects of fluorinated functional groups on the various properties of PEA derivatives. This analysis revealed the specific impact of fluorinated substitution on the various properties of PEA and three fluorine-substituted derivatives, namely PEA–F ( para -fluorophenylethylamine), PEA–CF 3 ( para -trifluoromethylphenyl ethylamine), and PEA–4F–CF 3 (4-trifluoromethyl-2,3,5,6-tetrafluorophenyl ethylamine). Specifically, as the molecular structure varied, corresponding changes were observed in molecular polarity, energy gap, surface electrostatic potentials, and spectral characteristic peaks. These variations are vital for understanding and predicting the potential applications of fluorinated phenethylamine derivatives.

Building a bridge between enzymatic and heterogeneous catalysis provides new cascade industrial processes for manufacturing. However, the reaction conditions of enzymatic and heterogeneous catalysis mutually cause deactivation of catalysts. Here, we overcame this challenge by developing a special protocol for the synthesis of hybrid catalysts. We utilized protein–polymer nanoconjugates as confined nanoreactors for the in situ synthesis of lipase–palladium (Pd) nanohybrids. The 0.8 nm Pd nanoparticles exhibited increased activity in racemization of ( S )-1-phenylethylamine. At 55 °C, which matches the optimum temperature of lipase, the activity is more than 50 times that of commercial Pd/C. It was found that the Pd–O coordination in Pd subnanoclusters contributed to the high activity. In the dynamic kinetic resolutions of pharmaceutical intermediates (±)-1-phenylethylamine, (±)-1-aminoindan and (±)-1,2,3,4-tetrahydro-1-naphthylamine, the lipase–Pd nanohybrids displayed 7.6, 3.1 and 5.0 times higher efficiencies than the combination of commercial immobilized lipase Novozym 435 and Pd/C. The lipase–Pd nanohybrids can be reused without agglomeration and activity loss. Combining enzymatic and heterogeneous catalysts is challenging due to different reaction requirements. Here, a method is presented constructing single protein–polymer nanoconjugates as nanoreactors for the in situ synthesis of enzyme–metal nanohybrids with high activity at ambient conditions.

β-phenylethylamine (PEA) is a neuroactive trace amine synthesized by the enzymatic decarboxylation of phenylalanine. PEA is involved in the improvement of mood and attention. Functional foods enriched in this compound could, therefore, be of interest to the food industry. PEA is produced by microbial activity in certain foods, but usually only in small amounts. The search for PEA-producing microorganisms with good technological properties is thus a pre-requisite if such functional foods are to be produced. This work reports the isolation of thirty-three PEA-producing bacterial strains from samples of different dairy products. They belong to the genus Enterococcus, and the species Levilactobacillus brevis. Identified strains of Enterococcus durans were then selected for technological characterization. Some of them showed properties of interest. In this species, PEA was determined to be produced via the action of tyrosine decarboxylase, encoded by the gene tdcA. This implies that, apart from PEA, a concomitant production of tyramine, a toxic biogenic amine, was observed.