An efficient synthesis of both enantiomers of lycoperdic acid, a 4-hydroxyglutamic acid derivative from edible mushroom Lycoperdon perlatum, was achieved from a chiral aminoalcohol. The key steps were a stereoselective introduction of a C3 unit into a bicyclic ketone and oxidative cleavage of a cyclic vicinal diol into a dicarboxylic acid. This report provides the first synthesis of (-)-lycoperdic acid.
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http://dx.doi.org/10.1093/bbb/zbaa027 | DOI Listing |
Int J Mol Sci
December 2024
Department of Chemistry and Biochemistry, Loyola University Chicago, 1032 West Sheridan Road, Chicago, IL 60660, USA.
Based on the inhibitory potencies from earlier reported tetrazole thioether analogs, we now describe the synthesis and inhibition of pyrazole-based inhibitors of -succinyl-l,l-2,6-diaminopimelic acid desuccinylase (DapE) from (DapE). The most potent pyrazole analog bears an aminopyridine amide with an IC of 17.9 ± 8.
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January 2025
Department of Pharmacy, Jilin Medical University, Jilin 132013, China.
An efficient stereoselective synthesis of 10-hydroxy-10-(1-indol-3-yl)-9-(10)-phenanthrene derivatives was realized through an organocatalyzed Friedel-Crafts reaction of phenanthrenequinones and indoles using a (,)-dimethylaminocyclohexyl-squaramide as the catalyst. Under the optimized conditions, the desired chiral products were obtained in good yields (73-90%) with moderate to high ee values (up to 97% ee). Two pairs of synthesized enantiomers were subjected to evaluation of their antiproliferative activities on four types of human cancer cell lines and one human umbilical vein endothelial cell line using the CCK-8 assay.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia.
Configurational differences in monosaccharides determine the products and selectivity of the transesterification reaction with lipase-B (CAL-B). The β-anomers of peresterified pyranose monosaccharides tend to yield anomeric deprotection products, while the α-anomers preferentially react at the sixth or fourth position. CAL-B differentiates between enantiomers, either reacting more rapidly with d-enantiomers of monosaccharides or having a different selectivity based on the enantiomer.
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December 2024
Xi'an Key Laboratory of Advanced Photo-Electronics Materials and Energy Conversion Device, Technological Institute of Materials & Energy Science (TIMES), Xijing University, Xi'an 710123, China.
Achieving superior circularly polarized luminescence brightness () is an important subject and continuous challenge for chiroptical materials. Herein, by applying a binary molecular design for the synthesis of chiral organo-Tb molecules, a novel pair of mononuclear chiral -pyrazolate-Tb enantiomers, [Tb(PMIP)(,-Ph-PyBox)] () and [Tb(PMIP)(,-Ph-PyBox)] (), have been synthesized and characterized. The three 1-phenyl-3-methyl-4-(isobutyryl)-5-pyrazolone () ligands play the role of efficient luminescence sensitizers and strong light-harvesting antennas, while the enantiopure 2,6-bis(4-phenyl-2-oxazolin-2-yl) pyridine ligand (/) is employed as the strong point-chiral inducer.
View Article and Find Full Text PDFInt J Mol Sci
December 2024
Department of Inorganic and Organic Chemistry, Faculty of Experimental Sciences, University of Jaén, Campus of International Excellence in Agri-Food (ceiA3), 23071 Jaén, Spain.
Human lactate dehydrogenase A (LDHA) is a homotetrameric isozyme involved in the conversion of glyoxylate into oxalate in the cytosol of liver cells (hepatocytes) and partially responsible for the overproduction of oxalate in patients with the rare disease called primary hyperoxaluria (PH). Recently, LDHA inhibition has been validated as a safe therapeutic method to try to control the PH disease. Stiripentol (STP) is an approved drug used in the treatment of seizures associated with Dravet's syndrome (a severe form of epilepsy in infancy) which, in addition, has been drawing interest in recent years also for potentially treating PH, due to its LDHA inhibitory activity.
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