Glycosyl fluorides can be prepared in an efficient manner by treatment of pyranose- or furanose-derived 1,2-orthoesters, with hydrogen fluoride pyridine (HF-py). The method is compatible with the presence of a variety of protecting groups, including tert-butyldiphenyl silyl ethers, and can be applied to sugar derivatives with free hydroxyl groups, thus avoiding the need for the protection-deprotection steps.
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http://dx.doi.org/10.1021/ol901630d | DOI Listing |
Int J Mol Sci
November 2024
Department of Cell Biology and Physiology, The University of Kansas Medical Center, Kansas City, KS 66103, USA.
Na,K-ATPase is the active ion transport system that maintains the electrochemical gradients for Na and K across the plasma membrane of most animal cells. Na,K-ATPase is constituted by the association of two major subunits, a catalytic α and a glycosylated β subunit, both of which exist as different isoforms (in mammals known as α1, α2, α3, α4, β1, β2 and β3). Na,K-ATPase α and β isoforms assemble in different combinations to produce various isozymes with tissue specific expression and distinct biochemical properties.
View Article and Find Full Text PDFOrg Lett
December 2024
Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi-502 284, Sangareddy, Telangana, India.
We developed an efficient method for synthesizing glycosyl fluorides from glycosyl hemiacetals using benzene-1,3-disulfonyl fluoride () as the fluorinating agent in combination with the base DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) under mild conditions.
View Article and Find Full Text PDFJ Org Chem
November 2024
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
Cage-shaped borates, whose Lewis acidity can be precisely modulated by the structural attributes of the triphenolic ligands, were employed as catalysts for glycosylation. Each cage-shaped borate displayed distinctive reactivity; thus, screening of the borate catalysts enabled controllable activation of glycosyl fluorides under mild conditions. Practical glycosylation was achieved by fine-tuning the Lewis acidity tailored to the substrate reactivity, thereby providing a versatile method applicable to the synthesis of complex glycans.
View Article and Find Full Text PDFEnzyme Microb Technol
December 2024
Department of Food and Biotechnology, Korea University, Sejong 30019, Republic of Korea. Electronic address:
This study presents the enzymatic synthesis of resveratrol-3,4'-O-α-diglucoside (RDG) using a hyperactive O-α-glycoligase (MalA-D416R/Q450S) and α-glucopyranosyl fluoride as the donor substrate. The transglycosylation rate for resveratrol by MalA-D416R/Q450S was maximized in 100 mM Tris-HCl (pH 9.5) containing 20 % DMSO at 45°C.
View Article and Find Full Text PDFOrg Lett
September 2024
Department of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, Michigan 48109-1055, United States.
Although aminosugars are important components in a variety of bioactive molecules, their stereoselective formation is made challenging by the Lewis basic nature of amino substituents. Additionally, the use of -acyl protecting groups is often problematic due to the competing formation of oxazolines during the glycosylation of 2-aminosugar derivatives. Herein, we report a boron-catalyzed strategy utilizing silyl ether glycosyl acceptors and 2-aminosugar donors that employs the 2,2,2-trichloroethoxycarbonyl (Troc) protecting group for the C2 amino functionality in glycosyl fluorides.
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