scholarly journals Synthesis of 3-Deoxy-d-manno-oct-2-ulosonic Acid (KDO) and Pseudaminic Acid C-Glycosides

2020 ◽  
Vol 85 (24) ◽  
pp. 16035-16042 ◽  
Author(s):  
Emmanuel Onobun ◽  
David Crich
Keyword(s):  
Pseudaminic Acid ◽  
Ulosonic Acid

scholarly journals Structure and In Vitro Bioactivity against Cancer Cells of the Capsular Polysaccharide from the Marine Bacterium Psychrobacter marincola

Marine Drugs ◽  
2020 ◽  
Vol 18 (5) ◽  
pp. 268
Author(s):  
Maxim S. Kokoulin ◽  
Alexandra S. Kuzmich ◽  
Lyudmila A. Romanenko ◽  
Irina V. Chikalovets ◽  
Oleg V. Chernikov
Keyword(s):  
Colony Formation ◽  
Marine Bacterium ◽  
Capsular Polysaccharide ◽  
In Vitro Bioactivity ◽  
First Finding ◽  
Pseudaminic Acid ◽  
Antitumor Properties ◽  
Ulosonic Acid ◽  
Human Acute Promyelocytic Leukemia

Psychrobacter marincola KMM 277T is a psychrophilic Gram-negative bacterium that has been isolated from the internal tissues of an ascidian Polysyncraton sp. Here, we report the structure of the capsular polysaccharide from P. marincola KMM 277T and its effect on the viability and colony formation of human acute promyelocytic leukemia HL-60 cells. The polymer was purified by several separation methods, including ultracentrifugation and chromatographic procedures, and the structure was elucidated by means of chemical analysis, 1-D, and 2-D NMR spectroscopy techniques. It was found that the polysaccharide consists of branched hexasaccharide repeating units containing two 2-N-acetyl-2-deoxy-d-galacturonic acids, and one of each of 2-N-acetyl-2-deoxy-d-glucose, d-glucose, d-ribose, and 7-N-acetylamino-3,5,7,9-tetradeoxy-5-N-[(R)-2-hydroxypropanoylamino]- l-glycero-l-manno-non-2-ulosonic acid. To our knowledge, this is the first finding a pseudaminic acid decorated with lactic acid residue in polysaccharides. The biological analysis showed that the capsular polysaccharide significantly reduced the viability and colony formation of HL-60 cells. Taken together, our data indicate that the capsular polysaccharide from P. marincola KMM 277T is a promising substance for the study of its antitumor properties and the mechanism of action in the future.

scholarly journals Granulibacter bethesdensis, a Pathogen from Patients with Chronic Granulomatous Disease, Produces a Penta-Acylated Hypostimulatory Glycero-d-talo-oct-2-ulosonic Acid–Lipid A Glycolipid (Ko-Lipid A)

2021 ◽  
Vol 22 (7) ◽  
pp. 3303
Author(s):  
Artur Muszyński ◽  
Kol A. Zarember ◽  
Christian Heiss ◽  
Joseph Shiloach ◽  
Lars J. Berg ◽  
...  
Keyword(s):  
Chronic Granulomatous Disease ◽  
Human Blood ◽  
Lipid A ◽  
Acid Resistance ◽  
Strong Acid ◽  
Granulomatous Disease ◽  
E Coli ◽  
Phagocyte Nadph Oxidase ◽  
Acyl Chains ◽  
Ulosonic Acid

Granulibacter bethesdensis can infect patients with chronic granulomatous disease, an immunodeficiency caused by reduced phagocyte NADPH oxidase function. Intact G. bethesdensis (Gb) is hypostimulatory compared to Escherichia coli, i.e., cytokine production in human blood requires 10–100 times more G. bethesdensis CFU/mL than E. coli. To better understand the pathogenicity of G. bethesdensis, we isolated its lipopolysaccharide (GbLPS) and characterized its lipid A. Unlike with typical Enterobacteriaceae, the release of presumptive Gb lipid A from its LPS required a strong acid. NMR and mass spectrometry demonstrated that the carbohydrate portion of the isolated glycolipid consists of α-Manp-(1→4)-β-GlcpN3N-(1→6)-α-GlcpN-(1⇿1)-α-GlcpA tetra-saccharide substituted with five acyl chains: the amide-linked N-3′ 14:0(3-OH), N-2′ 16:0(3-O16:0), and N-2 18:0(3-OH) and the ester-linked O-3 14:0(3-OH) and 16:0. The identification of glycero-d-talo-oct-2-ulosonic acid (Ko) as the first constituent of the core region of the LPS that is covalently attached to GlcpN3N of the lipid backbone may account for the acid resistance of GbLPS. In addition, the presence of Ko and only five acyl chains may explain the >10-fold lower proinflammatory potency of GbKo–lipidA compared to E. coli lipid A, as measured by cytokine induction in human blood. These unusual structural properties of the G.bethesdensis Ko–lipid A glycolipid likely contribute to immune evasion during pathogenesis and resistance to antimicrobial peptides.

scholarly journals Azide‐Functionalized Derivatives of the Virulence‐Associated Sugar Pseudaminic Acid: Chiral Pool Synthesis and Labeling of Bacteria

2021 ◽  
Author(s):  
Daniel B. Werz ◽  
Amol M. Vibhute ◽  
Hideki Tamai ◽  
Dana Logviniuk ◽  
Peter G. Jones ◽  
...  
Keyword(s):  
Pseudaminic Acid ◽  
Derivatives Of

ChemInform Abstract: Esterase Mediated Regioselective Deacetylation of Ulosonic Acid.

ChemInform ◽  
2010 ◽  
Vol 33 (39) ◽  
pp. no-no
Author(s):  
Balagurunathan Kuberan ◽  
Qun Wang ◽  
Mamoru Koketsu ◽  
Robert J. Linhardt
Keyword(s):  
Regioselective Deacetylation ◽  
Ulosonic Acid

scholarly journals A receptor-binding protein ofCampylobacter jejunibacteriophage NCTC 12673 recognizes flagellin glycosylated with acetamidino-modified pseudaminic acid

2014 ◽  
Vol 95 (1) ◽  
pp. 101-115 ◽  
Author(s):  
Muhammad Afzal Javed ◽  
Lieke B. van Alphen ◽  
Jessica Sacher ◽  
Wen Ding ◽  
John Kelly ◽  
...  
Keyword(s):  
Receptor Binding ◽  
Binding Protein ◽  
Pseudaminic Acid ◽  
Receptor Binding Protein

Total Synthesis ofPseudomonas aeruginosa1244 Pilin Glycan viade NovoSynthesis of Pseudaminic Acid

2017 ◽  
Vol 139 (38) ◽  
pp. 13420-13428 ◽  
Author(s):  
Han Liu ◽  
Yanfeng Zhang ◽  
Ruohan Wei ◽  
Gloria Andolina ◽  
Xuechen Li
Keyword(s):  
Total Synthesis ◽  
Pseudaminic Acid

scholarly journals Novel serine/threonine-O-glycosylation with N-acetylneuraminic acid and 3-deoxy-D-manno-octulosonic acid by bacterial flagellin glycosyltransferases

Glycobiology ◽  
2020 ◽  
Author(s):  
Aasawari Khairnar ◽  
Sonali Sunsunwal ◽  
Ponnusamy Babu ◽  
T N C Ramya
Keyword(s):  
Escherichia Coli ◽  
Clostridium Botulinum ◽  
Associated Factors ◽  
Nucleotide Sugar ◽  
Acetylneuraminic Acid ◽  
Geobacillus Kaustophilus ◽  
Nonulosonic Acid ◽  
Glycosyl Donor ◽  
Pseudaminic Acid ◽  
Substrate Promiscuity

Abstract Some bacterial flagellins are O-glycosylated on surface-exposed serine/threonine residues with nonulosonic acids such as pseudaminic acid, legionaminic acid and their derivatives by flagellin nonulosonic acid glycosyltransferases, also called motility-associated factors (Maf). We report here two new glycosidic linkages previously unknown in any organism, serine/threonine-O-linked N-acetylneuraminic acid (Ser/Thr-O-Neu5Ac) and serine/threonine-O-linked 3-deoxy-D-manno-octulosonic acid or keto-deoxyoctulosonate (Ser/Thr-O-KDO), both catalyzed by Geobacillus kaustophilus Maf and Clostridium botulinum Maf. We identified these novel glycosidic linkages in recombinant G. kaustophilus and C. botulinum flagellins that were coexpressed with their cognate recombinant Maf protein in Escherichia coli strains producing the appropriate nucleotide sugar glycosyl donor. Our finding that both G. kaustophilus Maf (putative flagellin sialyltransferase) and C. botulinum Maf (putative flagellin legionaminic acid transferase) catalyzed Neu5Ac and KDO transfer on to flagellin indicates that Maf glycosyltransferases display donor substrate promiscuity. Maf glycosyltransferases have the potential to radically expand the scope of neoglycopeptide synthesis and posttranslational protein engineering.

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