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Keywords = vicinal amino alcohols

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17 pages, 1346 KiB  
Review
Targeted Redox Regulation α-Ketoglutarate Dehydrogenase Complex for the Treatment of Human Diseases
by Ryan J. Mailloux
Cells 2025, 14(9), 653; https://doi.org/10.3390/cells14090653 - 29 Apr 2025
Viewed by 1074
Abstract
α-ketoglutarate dehydrogenase complex (KGDHc) is a crucial enzyme in the tricarboxylic acid (TCA) cycle that intersects monosaccharides, amino acids, and fatty acid catabolism with oxidative phosphorylation (OxPhos). A key feature of KGDHc is its ability to sense changes in the redox environment through [...] Read more.
α-ketoglutarate dehydrogenase complex (KGDHc) is a crucial enzyme in the tricarboxylic acid (TCA) cycle that intersects monosaccharides, amino acids, and fatty acid catabolism with oxidative phosphorylation (OxPhos). A key feature of KGDHc is its ability to sense changes in the redox environment through the reversible oxidation of the vicinal lipoic acid thiols of its dihydrolipoamide succinyltransferase (DLST; E2) subunit, which controls its activity and, by extension, OxPhos. This characteristic inculcates KGDHc with redox regulatory properties for the modulation of metabolism and mediating of intra- and intercellular signals. The innate capacity of KGDHc to participate in the regulation of cell redox homeodynamics also occurs through the production of mitochondrial hydrogen peroxide (mtH2O2), which is generated by the dihydrolipoamide dehydrogenase (DLD; E3) downstream from the E2 subunit. Reversible covalent redox modification of the E2 subunit controls this mtH2O2 production by KGDHc, which not only protects from oxidative distress but also modulates oxidative eustress pathways. The importance of KGDHc in modulating redox homeodynamics is underscored by the pathogenesis of neurological and metabolic disorders that occur due to the hyper-generation of mtH2O2 by this enzyme complex. This also implies that the targeted redox modification of the E2 subunit could be a potential therapeutic strategy for limiting the oxidative distress triggered by KGDHc mtH2O2 hyper-generation. In this short article, I will discuss recent findings demonstrating KGDHc is a potent mtH2O2 source that can trigger the manifestation of several neurological and metabolic diseases, including non-alcoholic fatty liver disease (NAFLD), inflammation, and cancer, and the targeted redox modification of the E2 subunit could alleviate these syndromes. Full article
(This article belongs to the Special Issue Charming Micro-Insights into Health and Diseases)
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19 pages, 2471 KiB  
Article
Thiol-Epoxy Click Chemistry: The Synthesis of Vicinal Amino Alcohols Containing a 1,2,4-Triazole Ring
by Artyom V. Petrosyan, Astghik A. Shahkhatuni, Andranik M. Davinyan, Karine S. Avetisyan, Tariel V. Ghochikyan, Melanya A. Samvelyan, Valentine G. Nenajdenko and Armen S. Galstyan
Chemistry 2025, 7(2), 53; https://doi.org/10.3390/chemistry7020053 - 1 Apr 2025
Cited by 1 | Viewed by 2632
Abstract
As examples of “Click Chemistry”, the reaction of 1-(oxiran-2-ylmethyl)piperidine with several 1,2,4-triazoles derivatives was studied. As a result, the reaction shows that the oxirane ring opens regiospecifically, according to Krasusky’s rule, without using a catalyst. The basic nitrogen present in 1-(oxiran-2-ylmethyl)piperidine has a [...] Read more.
As examples of “Click Chemistry”, the reaction of 1-(oxiran-2-ylmethyl)piperidine with several 1,2,4-triazoles derivatives was studied. As a result, the reaction shows that the oxirane ring opens regiospecifically, according to Krasusky’s rule, without using a catalyst. The basic nitrogen present in 1-(oxiran-2-ylmethyl)piperidine has a catalytic (anchimer) effect. Full article
(This article belongs to the Special Issue Celebrating the 50th Anniversary of Professor Valentine Ananikov)
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17 pages, 2304 KiB  
Article
Multi-Catalytic Route for the Synthesis of (S)-Tembamide
by Laura Leemans, Marc D. Walter, Frank Hollmann, Anett Schallmey and Luuk M. van Langen
Catalysts 2019, 9(10), 822; https://doi.org/10.3390/catal9100822 - 29 Sep 2019
Cited by 3 | Viewed by 4304
Abstract
Enantiopure β-amino alcohols constitute one of the most significant building blocks for the synthesis of active pharmaceutical ingredients. Despite the availability of a range of chiral β-amino alcohols from a chiral pool, there is a growing demand for new enantioselective synthetic routes to [...] Read more.
Enantiopure β-amino alcohols constitute one of the most significant building blocks for the synthesis of active pharmaceutical ingredients. Despite the availability of a range of chiral β-amino alcohols from a chiral pool, there is a growing demand for new enantioselective synthetic routes to vicinal amino alcohols and their derivatives. In the present study, an asymmetric 2-step catalytic route that converts 4-anisaldehyde into a β-amino alcohol derivative, (S)-tembamide, with excellent enantiopurity (98% enantiomeric excess) has been developed. The recently published initial step consists in a concurrent biocatalytic cascade for the synthesis of (S)-4-methoxymandelonitrile benzoate. The O-benzoyl cyanohydrin is then converted to (S)-tembamide in a hydrogenation reaction catalyzed by Raney Ni. To achieve hydrogenation of the nitrile moiety with highest chemoselectivity and enantioretention, various parameters such as nature of the catalyst, reaction temperature and hydrogen pressure were studied. The reported strategy might be transferrable to the synthesis of other N-acyl-β-amino alcohols. Full article
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13 pages, 4857 KiB  
Review
Impact of Wort Amino Acids on Beer Flavour: A Review
by Inês M. Ferreira and Luís F. Guido
Fermentation 2018, 4(2), 23; https://doi.org/10.3390/fermentation4020023 - 28 Mar 2018
Cited by 122 | Viewed by 19096
Abstract
The process by which beer is brewed has not changed significantly since its discovery thousands of years ago. Grain is malted, dried, crushed and mixed with hot water to produce wort. Yeast is added to the sweet, viscous wort, after which fermentation occurs. [...] Read more.
The process by which beer is brewed has not changed significantly since its discovery thousands of years ago. Grain is malted, dried, crushed and mixed with hot water to produce wort. Yeast is added to the sweet, viscous wort, after which fermentation occurs. The biochemical events that occur during fermentation reflect the genotype of the yeast strain used, and its phenotypic expression is influenced by the composition of the wort and the conditions established in the fermenting vessel. Although wort is complex and not completely characterized, its content in amino acids indubitably affects the production of some minor metabolic products of fermentation which contribute to the flavour of beer. These metabolic products include higher alcohols, esters, carbonyls and sulfur-containing compounds. The formation of these products is comprehensively reviewed in this paper. Furthermore, the role of amino acids in the beer flavour, in particular their relationships with flavour active compounds, is discussed in light of recent data. Full article
(This article belongs to the Special Issue Brewing & Distilling)
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