Occurrence and Significance

Wittmann, Valentin

doi:10.1007/978-3-642-56874-9_54

Cited by 7 publications

(2 citation statements)

References 118 publications

(92 reference statements)

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“…Glycoproteins are also found in the bacterial, vegetal and animal kingdoms as well; they can be inserted into the bilayer membrane either through embedment or by way of a GPI anchor. Their carbohydrate content can vary from less than 1% of the total weight of the glycoprotein (in some plant lectins) to more than 80% (in blood group glycoproteins) [2,3].…”

Section: Introductionmentioning

confidence: 99%

The use of glycolipids inserted in color-changeable polydiacetylene vesicles, as targets for biological recognition

Boullanger

Lafont

Bouchu

et al. 2007

Comptes Rendus. Chimie

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Topochemical organizations of conjugated diacetylenic acid photochemically polymerize to afford UVevisible absorbing polymers. Under the effect of an external stress caused by combination of the biomolecules to be recognized with the glycolipids on the vesicle surface, changes of conformation in the polymer backbone may result in a color change. Thus, monolayers and vesicles made of conjugated diacetylenic acid and a certain amount of glycolipids can be polymerized as far as the topochemical organization is not disrupted. In the presence of a protein (lectin, IgG, virus, etc.) or a microorganism (E. coli) able to bind with the glycolipid, the recognition at the interface resulted in a color change from blue to red. The synthesis of new glycolipids, and the study of their embedment into polydiacetylenic supramolecular assemblies allowed optimizing recognition parameters with regard to the structures of conjugated diynoic acids, the ideality of polydiacetylenic/glycolipidic mixtures, the polydiacetylene/glycolipid molar ratios, pH or vesicle sizes. The rapidity and the sensitivity of the phenomenon (often visible to the naked eye) together with the simplicity of its quantification (UVevisible spectrum) render it a good candidate for the development of biosensors.

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Section: Introductionmentioning

confidence: 99%

The use of glycolipids inserted in color-changeable polydiacetylene vesicles, as targets for biological recognition

Boullanger

Lafont

Bouchu

et al. 2007

Comptes Rendus. Chimie

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“…2-Amino-2-deoxyhexoses are among the most important modified sugars found in nature . 2-Acetamido-2-deoxy- d- glucose ( d- GlcNAc) is the most abundant 2-amino-2-deoxyhexose found in nature, and together with 2-acetamido-2-deoxy- d- galactose ( d- GalNAc), both constitute essential building blocks of bioactive oligosaccharides and glycoconjugates that include glycoproteins, glycopeptides, glycolipids, peptidoglycan, and glycosaminoglycans. , Other rare aminosugars such as 2-acetamido-2-deoxy- d- allosamine ( d- AllNAc) and 2-acetamido-2-deoxy- d- gulosamine ( d- GulNAc), are also found in nature. For example, d- AllNAc exists as a component of allosamidin, a selective and powerful chitinase inhibitor, and d- GulNAc was isolated from the antibiotic streptothricin F and streptolidin B (Figure ) .…”

Section: Introductionmentioning

confidence: 99%

Concise and Efficient Synthesis of 2-Acetamido-2-deoxy-β-d-hexopyranosides of Diverse Aminosugars from 2-Acetamido-2-deoxy-β-d-glucose

2008

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The furanose acetonide derivative 1 is readily prepared from 2-acetamido-2-deoxy-D-glucose on a large scale without the need for chromatography. Mesylation of 1 provides an efficient, concise, synthetic route to rare 2-acetamido-2-deoxy-beta-D-hexopyranosides (2 and 3) via the corresponding methyl 2-acetamido-2-deoxy-3-O-methanesulfonyl-beta-D-glucopyranoside and subsequent inversion of configuration by direct displacement or formation of a 3,4-epoxide. Opening of this epoxide by azide provided a direct route to methyl 2-acetamido-4-amino-2,4,6-trideoxy-beta-D-gulopyranoside 4. Benzylation of 1 followed by ring expansion to the glucopyranoside, deoxygenation at C-6, and subsequent displacement of a C-4 triflate permitted the synthesis of methyl 2-acetamido-4-amino-2,4,6-trideoxy-beta-D-galactopyranoside 5. Methyl 2-acetamido-2-deoxy-beta-D-glucopyranoside available from 1 in quantitative yield was readily converted to methyl 2-acetamido-2-deoxy-beta-D-galactopyranoside 6 (>60%) by inversion of configuration at C-4. Introduction of a lactyl substituent at C-3 of oxazoline 1 also provides a facile synthesis of the biologically important muramic acid beta-glycoside 7. An interesting reaction to convert 2-acetamido-2-deoxyhexopyranosides to the corresponding 2-deoxy-2-tetrazole is also reported.

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Copper(II)‐Mediated Activation of Sugar Oxazolines: Mild and Efficient Synthesis of β‐Glycosides of N ‐Acetylglucosamine

Wittmann

Lennartz

2002

European J Organic Chem

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Occurrence and Significance

Cited by 7 publications

References 118 publications

The use of glycolipids inserted in color-changeable polydiacetylene vesicles, as targets for biological recognition

The use of glycolipids inserted in color-changeable polydiacetylene vesicles, as targets for biological recognition

Concise and Efficient Synthesis of 2-Acetamido-2-deoxy-β-d-hexopyranosides of Diverse Aminosugars from 2-Acetamido-2-deoxy-β-d-glucose

Copper(II)‐Mediated Activation of Sugar Oxazolines: Mild and Efficient Synthesis of β‐Glycosides of N ‐Acetylglucosamine

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