A concise and efficient asymmetric Mannich/hemiketalization/retro-Henry cascade reaction between -hydroxy-α-aminosulfones and α-nitroketones was developed by utilizing a cinchona-derived bifunctional squaramide catalyst. This methodology provided access to β-nitro-substituted amino compounds with up to 95% yield and >99% ee. The practicality was demonstrated by scale-up and diverse derivatizations, including the synthesis of imidazolidinone and amino acid analogs. This is the first report of α-nitroketones in such a cascade reaction, offering a valuable approach for the synthesis of chiral β-nitro amino compounds.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.4c02491 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Highly Efficient Biosynthesis of Rebaudioside M9 through Enzyme Screening and Structure-Guided Engineering.
J Agric Food Chem
January 2025
Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, PR China.
Steviol glycosides (SGs) are highly valued for their sweetness, safety, and zero calories, but their bitter taste and low solubility limit their application. Modifying glycosyl units is a promising strategy to improve sensory qualities. In this study, we identified the enzyme UGT94E13 through phylogenetic analysis and enzyme screening, which catalyzes the glycosylation of rebaudioside M2 (Reb M2) at the C-13 position, producing the novel β-1,6--glycosylated product rebaudioside M9 (Reb M9).
View Article and Find Full Text PDFA review of the 's intervention mechanism and clinical application in ischemic stroke.
Front Pharmacol
January 2025
College of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, China.
Background: (BC), also named Niuhuang in Chinese, is utilized as a resuscitation drug in Traditional Chinese Medicine (TCM) for the treatment of neurological disorders. Ischemic stroke (IS) is a significant global public health issue that currently lacks safe and effective therapeutic drugs. Ongoing efforts are focused on identifying effective treatment strategies from Traditional, Complementary, and Integrative Medicine.
View Article and Find Full Text PDFTrehalose decorated nanostructures stabilize combined cross-linked enzyme aggregates (Combi-CLEAs) of β-galactosidase and glucose isomerase.
Int J Biol Macromol
January 2025
Department of Food Science, College of Agriculture and Life Sciences, Cornell University, Ithaca, NY 14853, USA. Electronic address:
Combined cross-linked enzyme aggregates (Combi-CLEAs) of β-Galactosidase (β-Gal) and Glucose Isomerase (GI) allow the transformation of d-lactose to lactose-fructose syrup through one-pot cascade biocatalytic reactions. Despite its promise, the low thermostability of β-Gal and high-temperature demands for GI limits this application. Trehalose is a protein-stabilizing disaccharide which has been utilized in immobilized enzyme systems to enhance protein thermostability.
View Article and Find Full Text PDFCofactor-directed co-immobilization of dual-enzyme on functionalized montmorillonite with enhanced catalytic performance.
Int J Biol Macromol
January 2025
School of Environment and Resource, Key Laboratory of Solid Waste Treatment and Resource Recycle of Ministry of Education, Southwest University of Science and Technology, Mianyang, Sichuan 621010, China.
Recently, multi-enzyme cascade catalysis has attracted increasing attention due to the advantages of integrating multiple enzymes, few side reactions and high catalytic efficiency. Herein, a novel dual-enzyme cascade system (GOx-FMt-HRP) was developed through cofactor-directed orientational co-immobilization of glucose oxidase (GOx) and horseradish peroxidase (HRP) onto functional montmorillonite (FMt). The presented method realizes the reconstitution of cofactors and apo-enzymes (enzymes without cofactors), which enables enzymes to be immobilized in specific orientations on the support, thereby effectively reducing changes in their conformation.
View Article and Find Full Text PDFConfined CHA-HCR system for sensitive and specific detection of ANXA2 mRNA in adenomyosis tissues.
J Pharm Biomed Anal
January 2025
Fujian Maternity and Child Health Hospital, College of Clinical Medicine for Obstetrics & Gynecology and Pediatrics, Fujian Medical University, Fuzhou, Fujian 350005, China; FujianKey Laboratory of Women and Children's Critical Diseases Research, Fuzhou, Fujian 350005, China. Electronic address:
Isothermal, enzyme-free amplification techniques, such as the hybridization chain reaction (HCR) and catalytic hairpin assembly (CHA), have gained significant attention for mRNA analysis. Despite their potential, these methods still face challenges, including false positives and low amplification efficiency. To overcome these limitations, we have developed a confined catalytic hairpin assembly and hybridization chain reaction (CHA-HCR) system that utilizes cholesterol-modified hairpin probes to enhance the sensitivity and specificity of mRNA detection.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!