10.1002/ejoc.201301015
The research focuses on the synthesis of the fungal lipo-chitooligosaccharide Myc-IV (C16:0, S), a key symbiotic signaling molecule in arbuscular mycorrhiza, which is an ancient and ecologically significant relationship between plants and fungi. The study outlines a novel synthetic approach involving critical steps such as oxidative cleavage of a 4,6-O-benzylidene acetal to prepare a disaccharidic glycosyl acceptor and stereoselective glycosylations with 2-methyl-5-tert-butylphenyl thioglycosyl donors. The experiments utilized various reactants, including N-acetylglucosamine derivatives, benzyloxycarbonyl (Z) protecting groups, and phthalimido (Phth) protecting groups, along with TBDPS protecting groups for stability. Analytical techniques employed in the study included mass spectrometry (MS), tandem mass spectrometry (MS/MS) for structural confirmation, and NMR spectroscopy for detailed analysis of the synthesized compounds. The research also discusses the potential agricultural applications of Myc factors or their analogues in stimulating mycorrhization and root system development.
10.1016/0008-6215(87)80145-3
The research details a novel synthesis of N-acetylneuraminic acid (Neu5Ac) and its deuterated analog [6-2H]-Neu5Ac from N-acetyl-D-glucosamine. The purpose of this study was to develop a straightforward and general method for synthesizing these compounds, which are crucial components of many glycoconjugates and are essential for studying the relationship between the structure of sialic acid residues and the function of glycoconjugates, as well as the mode of action of enzymes involved in their biosynthesis and transformation. The synthesis involves several key steps, including the Henry reaction of a 1-deoxy-1-nitro derivative of N-acetyl-D-glucosamine (protected 1-C-nitroanhydro-D-glucitol) with cyclohexylidene-α-glyceraldehyde, followed by acetylation, reductive denitration with Bu3SnH, debenzylation, catalytic oxidation, hydrolysis, esterification, and final acetylation. The study concludes that this method provides a convenient route for synthesizing Neu5Ac and its derivatives, allowing for modifications at various positions (C-1 to C-9) of the molecule, which can be useful for further studies and applications in glycobiology.
10.1016/j.bmc.2011.07.031
The study investigates the synthesis and neuroprotective effects of a series of novel aralkyl alcoholic 2-acetamido-2-deoxy-b-D-pyranosides on PC12 cells. The researchers aimed to improve neuroprotective effects for ischemic stroke treatment by synthesizing these compounds and testing their protective activities against hypoglycemia and serum limitation-induced cell death in rat pheochromocytoma cells (PC12 cells). The chemicals involved include salidroside, a phenylpropanoid glycoside known for its neuroprotective properties, and various aralkyl alcohols coupled with N-acetylglucosamine to form the target compounds. The study found that most of the synthesized compounds exhibited strong neuroprotective effects, with compounds 4g and 4h showing superior potency to salidroside. These compounds significantly attenuated cell viability loss and apoptotic cell death in PC12 cells, modulated apoptosis-related gene expression, and restored mitochondrial membrane potential, suggesting their potential as new neuroprotective agents for treating cerebral ischemic stroke and neurodegenerative diseases.
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