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Azide-Functionalized Derivatives of the Virulence-Associated Sugar Pseudaminic Acid: Chiral Pool Synthesis and Labeling of Bacteria.

ABSTRACT: Pseudaminic acid (Pse) is a significant prokaryotic monosaccharide found in important Gram-negative and Gram-positive bacteria. This unique sugar serves as a component of cell-surface-associated glycans or glycoproteins and is associated with their virulence. We report the synthesis of azidoacetamido-functionalized Pse derivatives as part of a search for Pse-derived metabolic labeling reagents. The synthesis was initiated with d-glucose (Glc), which served as a cost-effective chiral pool starting material. Key synthetic steps involve the conversion of C1 of Glc into the terminal methyl group of Pse, and inverting deoxyaminations at C3 and C5 of Glc followed by backbone elongation with a three-carbon unit using the Barbier reaction. Metabolic labeling experiments revealed that, of the four Pse derivatives, ester-protected C5 azidoacetamido-Pse successfully labeled cells of Pse-expressing Gram-positive and Gram-negative strains. No labeling was observed in cells of non-Pse-expressing strains. The ester-protected and C5 azidoacetamido-functionalized Pse is thus a useful reagent for the identification of bacteria expressing this unique virulence-associated nonulosonic acid.

SUBMITTER: Vibhute AM

PROVIDER: S-EPMC8360151 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:Overconsumption of highly sugary foods contributes to increases in obesity and diabetes in our population, and initiatives are issued worldwide to reduce sugar content in food products. However, it is unclear how the presentation of reduced sugar content on food packages affects taste expectations of consumers. Based on the learned knowledge about negative health effects of sugar and the common belief that unhealthy food tastes better than healthy food, consumers might conclude that lower sugar levels are associated with higher healthiness and lower tastiness. Addressing this concern, we examined how quantitative information about sugar content without any verbal description influences consumers' health and taste expectations of dairy desserts. We asked participants to indicate the expected healthiness and tastiness of randomly sampled dairy desserts, while varying systematically the quantitative sugar information provided in a label presented with the desserts (numerical sugar level in grams per 100 grams of product: low vs. original vs. high). We assumed that quantitative sugar content is not equally associated with healthiness and tastiness of products and that numerical information about sugar content informs health more than taste expectations. Therefore, we predicted that consumers expect higher healthiness, but not to the same degree lower tastiness for products with reduced sugar contented compared to products with higher sugar content. The results of the present study are in line with this hypothesis. We found that consumers expected desserts with less sugar to be healthier than desserts with higher levels of sugar. The experimentally varied sugar levels did not affect the tastiness expectations. Notably, consumers did not follow the unhealthy = tasty intuition and did not devaluate the tastiness of desserts because of heightened healthiness expectations. Our findings suggest that sole numerical information about sugar content-an important nutritional value-is more diagnostic in the construction of healthiness rather than tastiness expectations of food products.

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Azide-Functionalized Derivatives of the Virulence-Associated Sugar Pseudaminic Acid: Chiral Pool Synthesis and Labeling of Bacteria.

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