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Pyruvate ketal is a biologically essential moiety due to its key role as an intermediate in metabolic pathways, serving as a key precursor for the synthesis of various essential biomolecules in organisms. However, the / stereochemistry of pyruvate ketal is difficult to control through chemical methods. In this study, the acid-labile pyruvate ketal linked to the 4- and 6-positions of galactose was cautiously constructed, and the X-ray analysis of the -configured product was successfully obtained. Subsequently, the compound was used for the synthesis of zwitterionic polysaccharide A1 (PS A1) precursor, and a clear structural elucidation was applied by using nuclear magnetic resonance and X-ray.
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http://dx.doi.org/10.3762/bjoc.21.131 | DOI Listing |
Beilstein J Org Chem
August 2025
Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan.
Pyruvate ketal is a biologically essential moiety due to its key role as an intermediate in metabolic pathways, serving as a key precursor for the synthesis of various essential biomolecules in organisms. However, the / stereochemistry of pyruvate ketal is difficult to control through chemical methods. In this study, the acid-labile pyruvate ketal linked to the 4- and 6-positions of galactose was cautiously constructed, and the X-ray analysis of the -configured product was successfully obtained.
View Article and Find Full Text PDFCarbohydr Polym
January 2024
Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China; Laboratory for Marine Drugs and Bioproducts, National Laboratory for Marine Science and Technology
A pyruvylated and sulfated galactan from the green alga Dictyosphaeria cavernosa, designated PSG, was obtained by dilute alkali extraction, ion-exchange and gel filtration chromatography. The backbone of PSG was composed of 3-linked β-d-Galp units with partial sulfation on C-4 and C-6. Pyruvate ketals were linked to O-3 and O-4 of nonreducing terminal β-d-Galp, as well as O-4 and O-6 of 3-linked β-d-Galp.
View Article and Find Full Text PDFInt J Biol Macromol
September 2022
Department of Chemical and Biological Engineering, University at Buffalo, The State University of New York (SUNY), Buffalo, NY 14260-4200, USA. Electronic address:
Xanthan gum is a naturally occurring polysaccharide obtained from Xanthomonas campestris. The xanthan gum backbone consists of β-d-glucose linked like in cellulose. The trisaccharide β-d-mannose-(1-4)-α-d-glucuronic acid-(1-2)-α-d-mannose is linked to O(3) position of every other glucose residue.
View Article and Find Full Text PDFChin J Nat Med
June 2022
Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China. Electronic address:
Bacterial surface glycans perform a diverse and important set of biological roles, and have been widely used in the treatment of bacterial infectious diseases. The majority of bacterial surface glycans are decorated with diverse rare functional groups, including amido, acetamidino, carboxamido and pyruvate groups. These functional groups are thought to be important constituents for the biological activities of glycans.
View Article and Find Full Text PDFChemphyschem
June 2021
Department of Molecular Biotechnology and Health Sciences Molecular Imaging Centre, University of Torino, Via Nizza 52, 10126, Torino, Italy.