Work

Selective Molecular Sequestration with Concurrent Natural Product Functionalization and Derivatization: From Crude Natural Product Extracts to a Single Natural Product Derivative in One Step

Year: 2011

Type: article

Abstract: A resin-bound nitroso compound sequestered a single unexpected component from crude plant seed extracts. Several plants, including Piper nigrum, Eugenia caryophyllata, and Pimenta dioica, were extracted with organic solvent in the presence of a nitroso-containing resin. The nitroso resin selectively sequestered a single compound, β-caryophyllene, via a chemo- and regioselective ene reaction. The ene product was released from the resin, and proper selection of the solid-phase linker and cleavage cocktail allowed concomitant further transformation of the primary ene product to a novel functionalized polycycle. Preliminary studies indicate that the new hydroxylamine-containing natural product derivatives have antibiotic activity.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo201361s

Authors: Viktor Krchňák, Jaroslav Zajíček, Patricia A. Miller, Marvin J. Miller

Institution: University of Notre Dame

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funders: University of Notre Dame, National Institutes of Health, National Institute of General Medical Sciences

Awards: G3596472261, Derivatization/Functionalization of Natural Product(RMI)