Unknown

Dataset Information

0

Synthesis of zearalenone-16-?,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation.

ABSTRACT: The development of a reliable procedure for the synthesis of the 16-glucoside and 16-sulfate of the resorcylic acid lactone (RAL) type compound zearalenone is presented. Different protective group strategies were considered and applied to enable the preparation of glucosides and sulfates that are difficult to access up to now. Acetyl and p-methoxybenzyl protection led to undesired results and were shown to be inappropriate. Finally, triisopropylsilyl-protected zearalenone was successfully used as intermediate for the first synthesis of the corresponding mycotoxin glucoside and sulfate that are highly valuable as reference materials for further studies in the emerging field of masked mycotoxins. Furthermore, high stability was observed for aryl sulfates prepared as tetrabutylammonium salts. Overall, these findings should be applicable for the synthesis of similar RAL type and natural product conjugates.

SUBMITTER: Mikula H 

PROVIDER: S-EPMC4077526 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation.

Mikula Hannes H   Weber Julia J   Svatunek Dennis D   Skrinjar Philipp P   Adam Gerhard G   Krska Rudolf R   Hametner Christian C   Fröhlich Johannes J  

Beilstein journal of organic chemistry 20140515

The development of a reliable procedure for the synthesis of the 16-glucoside and 16-sulfate of the resorcylic acid lactone (RAL) type compound zearalenone is presented. Different protective group strategies were considered and applied to enable the preparation of glucosides and sulfates that are difficult to access up to now. Acetyl and p-methoxybenzyl protection led to undesired results and were shown to be inappropriate. Finally, triisopropylsilyl-protected zearalenone was successfully used a  ...[more]

Similar Datasets

Unknown Biosynthesis and Characterization of Zearalenone-14-Sulfate, Zearalenone-14-Glucoside and Zearalenone-16-Glucoside Using Common Fungal Strains.
| S-EPMC5869392 | biostudies-literature
Unknown Greensporones: resorcylic acid lactones from an aquatic Halenospora sp.
| S-EPMC4176394 | biostudies-literature
Unknown Antifungal and Cytotoxic β-Resorcylic Acid Lactones from a Paecilomyces Species.
| S-EPMC5819736 | biostudies-literature
Unknown Studies of mammalian glucoside conjugation.
| S-EPMC1177583 | biostudies-other
Unknown Resorcylic acid lactones with cytotoxic and NF-?B inhibitory activities and their structure-activity relationships.
| S-EPMC3111092 | biostudies-literature
Unknown Discovery, Semisynthesis, Antiparasitic and Cytotoxic Evaluation of 14-Membered Resorcylic Acid Lactones and Their Derivatives.
| S-EPMC5603512 | biostudies-other
Unknown Zearalenone-14-Glucoside Is Hydrolyzed to Zearalenone by β-Glucosidase in Extracellular Matrix to Exert Intracellular Toxicity in KGN Cells.
| S-EPMC9316695 | biostudies-literature
Unknown Insights into the biosynthesis of 12-membered resorcylic acid lactones from heterologous production in Saccharomyces cerevisiae.
| S-EPMC4033647 | biostudies-literature
Unknown Neocosmospora sp.-derived resorcylic acid lactones with in vitro binding affinity for human opioid and cannabinoid receptors.
| S-EPMC3723356 | biostudies-literature
Unknown Enzymatic synthesis of resorcylic acid lactones by cooperation of fungal iterative polyketide synthases involved in hypothemycin biosynthesis.
| S-EPMC2861853 | biostudies-literature