The tandem Friedel-Crafts conjugate addition/asymmetric protonation reaction between 2-substituted indoles and methyl 2-acetamidoacrylate is reported. The reaction is catalyzed by (R)-3,3'-dibromo-BINOL in the presence of stoichiometric SnCl(4), and is the first example of a tandem conjugate addition/asymmetric protonation reaction using a BINOL·SnCl(4) complex as the catalyst. A range of indoles furnished synthetic tryptophan derivatives in good yields and high levels of enantioselectivity, even on a preparative scale. The convergent nature of this transformation should lend itself to the preparation of unnatural tryptophan derivatives for use in a broad array of synthetic and biological applications.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3310256 | PMC |
| http://dx.doi.org/10.1021/ja209390d | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Effects of acteoside from on the plasma metabolome of cancer-related fatigue mice inoculated with colon cancer cells.
Front Pharmacol
January 2025
Department of Pharmacognosy, School of Pharmacy, Xinjiang Medical University, Urumqi, China.
Objective: To elucidate the metabolic mechanisms by which acteoside (ACT) isolated from alleviates cancer-related fatigue (CRF) in a murine model of colon cancer with cachexia.
Methods: BALB/c mice inoculated with C26 colon cancer cells were treated with paclitaxel (PTX, 10 mg/kg) and ACT (100 mg/kg) alone or in combination for 21 days. Fatigue-associated behaviors, tumor inhibition rate, and skeletal muscle morphology assessed by hematoxylin-eosin (H&E) staining and electron microscopy were evaluated.
Fucoidan exerts antitumor effects by regulating gut microbiota and tryptophan metabolism.
Int J Biol Macromol
January 2025
State Key Laboratory of Marine Food Processing & Safety Control, College of Food Science and Engineering, Ocean University of China, China.
Fucoidan, a water-soluble polysaccharide derived from marine organisms, has garnered significant attention for its ability to regulate gut microbiota and its anti-tumor properties. However, the existence of a correlation between the anti-tumor effect of fucoidan and its regulation of the gut microbiota remains unknown. In pursuit of this objective, we culled the gut microbiota of mice with broad-spectrum antibiotics to generate pseudo-sterile tumor-bearing mice.
View Article and Find Full Text PDFOn the Biosynthesis of Bioactive Tryptamines in Black Cohosh ( L.).
Plants (Basel)
January 2025
Institute for Bioscience and Biotechnology Research, University of Maryland, Rockville, MD 20850, USA.
Botanical dietary supplements are widely used, but issues of authenticity, consistency, safety, and efficacy that complicate their poorly understood mechanism of action have prompted questions and concerns in the popular and scientific literature. Black cohosh ( L., syn.
View Article and Find Full Text PDFRelationship Between the Gut Microbiome, Tryptophan-Derived Metabolites, and Osteoarthritis-Related Pain: A Systematic Review with Meta-Analysis.
Nutrients
January 2025
Grupo de Investigación en Calidad de Vida y Salud, Departamento de Ciencias de la Salud, Universidad Europea de Valencia, 03016 Alicante, Spain.
Introduction: Osteoarthritis (OA) is the most prevalent form of arthritis and affects over 528 million people worldwide. Degenerative joint disease involves cartilage degradation, subchondral bone remodeling, and synovial inflammation, leading to chronic pain, stiffness, and impaired joint function. Initially regarded as a "wear and tear" condition associated with aging and mechanical stress, OA is now recognized as a multifaceted disease influenced by systemic factors such as metabolic syndrome, obesity, and chronic low-grade inflammation.
View Article and Find Full Text PDFEvaluation of In Vitro Production Capabilities of Indole Derivatives by Lactic Acid Bacteria.
Microorganisms
January 2025
Institute of Food Sciences, Shanxi Normal University, Taiyuan 030031, China.
Lactic acid Bacteria (LAB) convert tryptophan to indole derivatives and induce protective IL-22 production in vivo. However, differences in metabolizing capabilities among LAB species have not been widely investigated. In the present study, we compared the capabilities of 186 LAB strains to produce four kinds of indole derivatives, including indole-3-carboxaldehyde (IAId), indole-3-lactic acid (ILA), indole-3-propanoic acid (IPA), and indole-3-acetic acid (IAA).
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!