Biomimetic Total Synthesis of (±)-Carbocyclinone-534 Reveals Its Biosynthetic Pathway.

Org Lett

State Key Laboratory of Phytochemistry and Plant Resources in West China and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, 132 Lanhei Road, Kunming 100049, China.

Published: December 2020

AI Article Synopsis

  • Carbocyclinone-534 is a newly discovered antibiotic derived from the metabolism of tapinarof.
  • The researchers developed a biomimetic total synthesis method for producing this antibiotic in just eight steps using a series of chemical reactions.
  • This synthesis method offers direct experimental insights into the biological process that creates carbocyclinone-534.

Article Abstract

Carbocyclinone-534 is a new antibiotic produced after the metabolism of tapinarof. We identify a biomimetic total synthesis of carbocyclinone-534 in eight steps by taking advantage of an intermolecular Diels-Alder homodimerization/dehydrogenation/intramolecular Diels-Alder cycloaddition cascade. This synthetic sequence provides direct experimental evidence for revealing the biosynthetic pathway of carbocyclinone-534.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.0c02865DOI Listing

Publication Analysis

Top Keywords

biomimetic total
8
total synthesis
8
biosynthetic pathway
8
pathway carbocyclinone-534
8
synthesis ±-carbocyclinone-534
4
±-carbocyclinone-534 reveals
4
reveals biosynthetic
4
carbocyclinone-534 antibiotic
4
antibiotic produced
4
produced metabolism
4

Similar Publications

This study aimed to evaluate the effectiveness of bioactive toothpastes in remineralizing eroded enamel surfaces in vitro. Bovine enamel blocks (n = 48) were obtained and classified into untreated, demineralized, and treated areas. Specimens were randomly classified into six groups (n = 8 each): fluoride-free toothpaste (NCT), Colgate Total 12 (PCT), Sensodyne Repair and Protect (SRP), Sensodyne Pronamel (SPE), Regenerador + Sensitive (RGS), and RGS/calcium booster (RCB).

View Article and Find Full Text PDF

This study explores mesoporous bioactive glasses (MBGs) that show promise as advanced therapeutic delivery platforms owing to their tailorable porous properties enabling enhanced drug loading capacity and biomimetic chemistry for localized, sustained release. This work systematically investigates the complex relationship between MBG composition and surfactant templating on structural evolution, bioactive response, resultant drug loading efficiency and release. A total of 12 samples of sol-gel-derived MBG were synthesized using cationic and non-ionic structure-directing agents (cetyltrimethylammonium bromide, Pluronic F127 and P123) while modulating the SiO/CaO content, generating MBG with surface areas of 60-695 m/g.

View Article and Find Full Text PDF

Nabumetone (NAB) is a poorly soluble nonsteroidal anti-inflammatory prodrug (BCS class II drug) whose solubility is significantly improved by complexation with cyclodextrins (CDs). : The solid complexes, in a 1:1 molar ratio, were prepared by mechanochemical activation by grinding, using β-cyclodextrin (β-CD) and its derivatives, hydroxypropyl- and sulfobutylether-β-cyclodextrin (HP-β-CD and SBE-β-CD). The complexation was confirmed by differential scanning calorimetry (DSC), powder X-ray diffraction (PXRD), and attenuated total reflectance Fourier-transformed infrared spectroscopy (ATR-FTIR).

View Article and Find Full Text PDF

Bioinspired surface structures for added shear stabilization in suction discs.

Sci Rep

January 2025

John A. Paulson School of Engineering and Applied Sciences, Harvard University, Boston, MA, 02134, USA.

Many aquatic organisms utilize suction-based organs to adhere to diverse substrates in unpredictable environments. For multiple fish species, these adhesive discs include a softer disc margin consisting of surface structures called papillae, which stabilize and seal on variable substrates. The size, arrangement, and density of these papillae are quite diverse among different species, generating complex disc patterns produced by these structures.

View Article and Find Full Text PDF

The effect of conditioned medium from human amniotic membrane-derived mesenchymal stem cells on thymus involution.

Life Sci

January 2025

3B's Research Group, I3Bs - Research Institute on Biomaterials, Biodegradables and Biomimetics, University of Minho, Headquarters of the European Institute of Excellence on Tissue Engineering and Regenerative Medicine, Guimarães, Portugal; ICVS/3B's-PT Government Associate Laboratory, Braga/Guimarães, Portugal. Electronic address:

Aims: The development and selection of T cells occur within the thymus. This organ involutes throughout life, compromising the generation of T cells and, consequently, the efficacy of the immune system. Mesenchymal stem cells (MSC) have beneficial effects on the immune system.

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!