A new approach to the tetracycline core structure is presented. The pivotal intermediate is identified as macrocycle III. The two interior bonds (C4a-C12a and C5a-C11a) are to be constructed through sequential transannular Michael additions (III-II) and compression-promoted transannular isoxazole alkylations from intermediate II.

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol302691jDOI Listing

Publication Analysis

Top Keywords

approach tetracycline
8
michael additions
8
macrocyclic approach
4
tetracycline natural
4
natural products
4
products investigation
4
investigation transannular
4
transannular alkylations
4
alkylations michael
4
additions approach
4

Similar Publications

The extensive use of tetracyclines in livestock poses health risks due to their residues in animal-derived food; therefore, developing simple detection methods to replace complex traditional approaches is of paramount importance. Here, we developed a dual-ligand zinc-based metal-organic framework material, Zn-BTC-BDC-NH (denoted as ZTD), for the detection of tetracyclines. The intrinsic blue fluorescence of ZTD was quenched upon the introduction of tetracyclines due to electron transfer from -NH of ZTD to -CO- and -OH groups of tetracycline molecules; meanwhile, the new green fluorescence emission was generated through π-π stacking between aromatic rings and the formation of complexes between Zn and C-O/C═O groups.

View Article and Find Full Text PDF

There are few in vitro models available to study microglial physiology in a homeostatic context. Recent approaches include the human induced pluripotent stem cell model, but these can be challenging for large-scale assays and may lead to batch variability. To advance our understanding of microglial biology while enabling scalability for high-throughput assays, we developed an inducible immortalized murine microglial cell line using a tetracycline expression system.

View Article and Find Full Text PDF

Rheumatoid arthritis (RA) is a chronic autoimmune disease characterized by persistent inflammation, joint pain, and progressive cartilage and bone erosion. Despite advancements in RA management with disease-modifying antirheumatic drugs (DMARDs) and biologics, some patients remain refractory to conventional treatments. Tetracyclines, such as minocycline and doxycycline, exhibit anti-inflammatory and immunomodulatory properties, making them potential supplementary treatments.

View Article and Find Full Text PDF

Background: Thermophilic species are among the main culprits behind bacterial gastroenteritis globally and have grown progressively resistant to clinically important antimicrobials. Many studies have been carried out to explore innovative and alternative strategies to control antibiotic-resistant campylobacters in animal reservoirs and human hosts; however, limited studies have been performed to develop efficient control schemes against biofilms.

Methods: This study investigated the antimicrobial and antibiofilm activities of some herbal extracts against multidrug-resistant (MDR) species recovered from different sources using phenotypic and molecular techniques.

View Article and Find Full Text PDF

Tracking the Prevalence of Antibiotic Resistance in Within the Spanish Poultry Industry: Insights from a One Health Approach.

Antibiotics (Basel)

December 2024

Centro de Calidad Avícola y Alimentación Animal de la Comunidad Valenciana (CECAV), 12539 Alquerias del Niño Perdido, Spain.

/: Antimicrobial resistance (AMR) in species from poultry production represents a significant public health threat due to the potential transmission of AMR through the food chain. This study aimed to examine the relative prevalence, resistance patterns, and mannitol fermentation capacity of isolates from various poultry production systems in Spain over a seven-year period (2017-2023). : A total of 215 isolates were analyzed.

View Article and Find Full Text PDF

Want 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!