Pachycarpine (4), the optical antipode of the lupine alkaloid (-)-sparteine (1), has been prepared from (-)-lupanine; its metabolism was studied in rats. After isolation and chromatographic purification, streochemically homogeneous (+)-(4S)-hydroxysparteine (7) was identified as the major urinary metabolite by use of mass spectrometry and high-field NMR-spectroscopy.
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http://dx.doi.org/10.1002/ardp.19893220704 | DOI Listing |
Org Lett
January 2025
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Chemical Biology Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, People's Republic of China.
We present a versatile palladium-catalyzed glycosylation platform that enables facile access to structurally diverse N-O-linked glycosides with constantly excellent regio- and stereoselectivities. Importantly, this approach offers a broad substrate scope, low catalyst loadings, and outstanding chemoselectivity, allowing for the selective reaction of oximes/hydroximic acids over hydroxyl groups that would otherwise pose challenges in conventional glycosylation methods. The synthetic utility of this method is further exemplified through a range of synthetic transformations and late-stage modification of bioactive molecules.
View Article and Find Full Text PDFBiochemistry
January 2025
Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.
CYP105A1 exhibits monooxygenase activity to a wide variety of structurally different substrates with regio- and stereospecificity, making its application range broad. Our previous studies have shown that CYP105A1 wild type and its variants metabolize 12 types of nonsteroidal anti-inflammatory drugs (NSAIDs). In particular, the R84A variant exhibited a high activity against many NSAIDs.
View Article and Find Full Text PDFJ Nat Prod
December 2024
Institut für Pharmazeutische Biologie und Biotechnologie, Fachbereich Pharmazie, Philipps-Universität Marburg, Robert-Koch-Straße 4, Marburg 35037, Germany.
A three-gene cluster from was proven to be responsible for the formation of -l-Trp-l-Leu (cWL) derivatives. An strain harboring the cyclodipeptide synthase (CDPS) gene produced cWL. Expression of the whole cluster or genes of various combinations in revealed different metabolites of cWL by two cytochrome P450 enzymes.
View Article and Find Full Text PDFPlant J
December 2024
Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3, Canada.
J Am Chem Soc
November 2024
Department of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, U.K.
Stereoselective alkene 1,2-difunctionalization is a privileged strategy to access three-dimensional C(sp)-rich chiral molecules from readily available "flat" carbon feedstocks. State-of-the-art approaches exploit chiral transition metal-catalysts to enable high levels of regio- and stereocontrol. However, this is often achieved at the expense of a limited alkene scope and reduced generality.
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