The BF3-promoted glycosylation of D-mannofuranurono-6,3-lactone with dodecanol or methanol afforded n-alkyl beta-D-mannofuranosidurono-6,3-lactone. Reduction of n-dodecyl beta-D-mannofuranosidurono-6,3-lactone with sodium borohydride yielded the corresponding alkyl beta-D-mannofuranoside.
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http://dx.doi.org/10.1016/s0008-6215(02)00439-1 | DOI Listing |
Chemistry
February 2024
Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Alberta, T2N 1N4, Canada.
The enzyme-resistant thioglycosides are highly valuable immunogens because of their enhanced metabolic stability. We report the first synthesis of a family of thiooligosaccharides related to the capsular polysaccharides (CPS) of Campylobacter jejuni HS:4 for potential use in conjugate vaccines. The native CPS structures of the pathogen consist of a challenging repeating disaccharide formed with β(1→4)-linked 6-deoxy-β-D-ido-heptopyranoside and N-acetyl-D-glucosamine; the rare 6-deoxy-ido-heptopyranosyl backbone and β-anomeric configuration of the former monosaccharide makes the synthesis of this family of antigens very challenging.
View Article and Find Full Text PDFCarbohydr Res
January 2023
Department of Chemistry & Chemical Biology, Indian Institute of Technology (ISM) Dhanbad, Dhanbad, 826004, Jharkhand, India. Electronic address:
Herein, we report the direct conversion of anomeric hydroxides to glycosyl azides in one step using diphenylphosphoryl azide. Protecting group manipulations on the hexose sugars have enabled the stereoselective synthesis of either the α-glycosyl azides or the β-anomeric azides in moderate to very good yields. The reaction has also been successfully used to enable the synthesis of β-2-deoxy-2-aminoglucosyl azides.
View Article and Find Full Text PDFRSC Adv
December 2021
Department of Chemistry, University of Utah 315 South 1400 East, Room 2020 Salt Lake City Utah 84112 USA
Herein we present a new high-throughput screening method for carbohydrate syntheses based on cyclic ion mobility spectrometry-mass spectrometry (cIMS-MS)-based separations. We rapidly resolved the α/β anomers for carbohydrates with varying protecting groups after only 5 m of cIMS-MS separation and also detected their respective unwanted anomeric impurities at levels lower than 2%. All experiments were performed in 1 minute of total acquisition time demonstrating our method's high-throughput nature.
View Article and Find Full Text PDFChembiochem
April 2022
Department of Chemistry, University of Natural Resources and Life Sciences-Vienna, Muthgasse 18, Wien, A-1190, Vienna, Austria.
Oligomannose-type glycans on the spike protein of HIV-1 constitute relevant epitopes to elicit broadly neutralizing antibodies (bnAbs). Herein we describe an improved synthesis of α- and β-linked hepta- and nonamannosyl ligands that were subsequently converted into BSA and CRM neoglycoconjugates. We assembled the ligands from anomeric 3-azidopropyl spacer glycosides from select 3-O-protected thiocresyl mannoside donors.
View Article and Find Full Text PDFProc Natl Acad Sci U S A
August 2017
Department of Medicine, Division of Rheumatology, Immunology, and Allergy, Brigham and Women's Hospital, Harvard Medical School, Boston, MA 02115;
Glycolipid antigens recognized by αβ T-cell receptors (TCRs) drive the activation of invariant natural killer T (iNKT) cells, a specialized subset of innate T lymphocytes. Glycolipids with α-linked anomeric carbohydrates have been identified as potent microbial lipid antigens for iNKT cells, and their unusual α-anomeric linkage has been thought to define a "foreign" lipid antigen motif. However, mammals use endogenous lipids to select iNKT cells, and there is compelling evidence for iNKT cell responses in various types of sterile inflammation.
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