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Synthesis of Glycosylphosphatidylinositol Analogues with an Unnatural -D-Glucosamine-(1→6)--Inositol Motif.
J Carbohydr Chem
April 2024
Department of Chemistry, University of Florida, 214 Leigh Hall, Gainesville, FL 32611, USA.
Glycosylphosphatidylinositol (GPI) anchors contain a unique α-D-glucosamine-(1→6)--inositol [αGlcN(1,6)Ins] motif in their conserved core structure. To facilitate investigations of the functional roles of this structural motif, two GPI analogues containing unnatural βGlcN(1,6)Ins, instead of αGlcN(1,6)Ins, and an alkyne group at different positions of the GPI core were designed and synthesized. To this end, an orthogonally protected pseudopentasaccharide derivative of GPIs with the βGlcN(1,6)Ins motif was convergently constructed via [3+2] glycosylation and used as the common intermediate to prepare both GPI analogues by streamlined synthetic protocols.
View Article and Find Full Text PDFPhysical properties of chlorophyll-quinone conjugates prepared via Friedel-Crafts reaction.
Photosynth Res
January 2025
Graduate School of Life Sciences, Ritsumeikan University, Kusatsu, Shiga, 525-8577, Japan.
Pheophytin-a derivatives possessing plastoquinone and phylloquinone analogs in the peripheral 3-substituent were prepared by Friedel-Crafts reactions of a 3-hydroxymethyl-chlorin as one of the chlorophyll-a derivatives with benzo- and naphthohydroquinones, respectively, and successive oxidation of the 1,4-dihydroxy-aryl groups in the resulting dehydration products. The 3-quinonylmethyl-chlorins exhibited ultraviolet-visible absorption and circular dichroism spectra in acetonitrile, which were composed of those of the starting 3-hydroxymethyl-chlorin and the corresponding methylated benzo- and naphthoquinones. No intramolecular interaction between the chlorin and quinone π-systems was observed in the solution owing to the methylene spacer.
View Article and Find Full Text PDFA Simple and Efficient Stereoselective Synthesis of a 2,3-Difluorosialic acid-based influenza virus neuraminidase inhibitor.
Chemistry
January 2025
Griffith University - Gold Coast Campus, Institute for Biomedicine and Glycomics, Parklands Drive, 4222, Southport, AUSTRALIA.
3-Fluoroneuraminosyl fluorides are invaluable probes for studying the catalytic mechanism of sialidases (neuraminidases), and as sialidase inhibitors. Significantly, when a C-3 equatorial fluorine is installed on a C-4 functionalised N-acylneuraminic acid (Neu)-based template, the compounds are potent and selective inhibitors of both influenza and parainfluenza sialidases, and of virus replication. Typically, the reported syntheses of 3-fluoroneuraminosyl fluorides involve either an enzymatic or a chemical synthesis that have uncontrolled stereoselectivity in the introduction of fluorine at C-3 of Neu and consequently yield a mixture of C-3 ax and C-3 eq fluoro derivatives.
View Article and Find Full Text PDFPatent review of novel compounds targeting opioid use disorder (2018-2024).
Expert Opin Ther Pat
January 2025
Department of Pharmaceutical and Biomedical Sciences, Rudolph H. Raabe College of Pharmacy, Ohio Northern University, Ada, OH, USA.
Introduction: Opioids have served as a cornerstone in pain management for decades. However, the emergence of increasingly potent synthetic analogs brings forth a range of side effects, including respiratory depression, tolerance, dependence, constipation, and, more importantly, the development of severe and debilitating opioid use disorder (OUD). Search for therapeutics to mitigate OUD has been challenging and this has called for novel approaches that include design of small molecules targeting neuronal circuits involved in addiction (opioid, dopamine, serotonin, norepinephrine, and glutamate receptors, etc.
View Article and Find Full Text PDFAltering Lipid A Precursor Ion Types in the Gas Phase for In-Depth Structural Elucidation via Tandem Mass Spectrometry.
Anal Chem
January 2025
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, United States.
Lipid A, a well-known saccharolipid, acts as the inner lipid-glycan anchor of lipopolysaccharides in Gram-negative bacterial cell membranes and functions as an endotoxin. Its structure is composed of two glucosamines with β(1 → 6) linkages and various fatty acyl and phosphate groups. The lipid A structure can be used for the identification of bacterial species, but its complexity poses significant structural characterization challenges.
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