The synthesis from l-arabinose of an azetidine analogue of 6,7-diepicastanospermine and its glycosidase inhibition profile are described.
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Harnessing Oxetane and Azetidine Sulfonyl Fluorides for Opportunities in Drug Discovery.
J Am Chem Soc
December 2024
Department of Chemistry, Imperial College London, Molecular Sciences Research Hub, White City Campus, Wood Lane, London W12 0BZ, U.K.
Four-membered heterocycles such as oxetanes and azetidines represent attractive and emergent design options in medicinal chemistry due to their small and polar nature and potential to significantly impact the physiochemical properties of drug molecules. The challenging preparation of these derivatives, especially in a divergent manner, has severely limited their combination with other medicinally and biologically important groups. Consequently, there is a substantial demand for mild and effective synthetic strategies to access new oxetane and azetidine derivatives and molecular scaffolds.
View Article and Find Full Text PDFMechanism of action of the toxic proline mimic azetidine 2-carboxylic acid in plants.
Plant J
December 2024
Department of Biochemistry, Interdisciplinary Plant Group, University of Missouri, Columbia, Missouri, USA.
Article Synopsis
- Plants use toxic metabolites to outcompete others for resources, targeting key processes like protein synthesis.
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"Angular" Spirocyclic Azetidines: Synthesis, Characterization, and Evaluation in Drug Discovery.
Angew Chem Int Ed Engl
December 2024
Enamine Ltd, Winston Churchill st. 78, 02094, Kyiv, Ukraine.
The previously neglected "angular" spirocyclic azetidines have been synthesized, characterized, and validated in drug discovery. We have shown that these compounds could act as bioisosteres for common saturated six-membered heterocycles. Their incorporation into the structure of the anticancer drug Sonidegib (instead of morpholine), and Danofloxacine (instead of piperazine) provided novel patent-free analogs with similar physicochemical properties and high activity.
View Article and Find Full Text PDFA comprehensive review of the proline mimic azetidine-2-carboxylic acid (A2C).
Toxicology
January 2025
The Neurotoxin Research Group, The University of Technology Sydney, Australia.
The imino acid azetidine-2-carboxylic acid (A2C), a proline homologue, was first identified in liliaceous plants in 1955. Its ability to exchange for proline in protein synthesis is responsible for its teratogenic effects and has made it a very useful tool for generating non-native proteins to study proteotoxic stress and ER stress. The tRNA synthetases from some A2C-producing plants can discriminate between proline and A2C, but for most plants and for mammalian cells, A2C is mistakenly used in protein synthesis in place of proline and can avoid cell proof-reading mechanisms.
View Article and Find Full Text PDFMolecular-based characterization and bioengineering of Sorghum bicolor to enhance iron deficiency tolerance in iron-limiting calcareous soils.
Plant Mol Biol
October 2024
Research Institute for Bioresources and Biotechnology, Ishikawa Prefectural University, 1-308 Suematsu, Nonoichi, Ishikawa, 921-8836, Japan.
Plant biomass can significantly contribute to alternative energy sources. Sorghum bicolor is a promising plant for producing energy, but is susceptible to iron deficiency, which inhibits its cultivation in iron-limiting calcareous soils. The molecular basis for the susceptibility of sorghum to iron deficiency remains unclear.
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