Synthesis and Quantitative Evaluation of <i>Glycero</i>‐<scp>D</scp>‐<i>manno</i>‐heptose Binding to Concanavalin A by Fluorous‐Tag Assistance

Jaipuri, Firoz A.; Collet, Béatrice; Pohl, Nicola L. B.

doi:10.1002/anie.200704262

Cited by 96 publications

(51 citation statements)

References 35 publications

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“…Our method can also be used to conduct parallel synthesis through the introduction of a fluorous affinity tag. The fluorous affinity-tagged technique has been previously employed for preparing tagged monosaccharide conjugates for carbohydrate-based microarray to determine the structural specificities of the interactions of proteins and carbohydrates (32).…”

Section: Substratesmentioning

confidence: 99%

Chemoenzymatic Design of Heparan Sulfate Oligosaccharides*

Liu

Chen

et al. 2010

Journal of Biological Chemistry

148

193

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Heparan sulfate is a sulfated glycan that exhibits essential physiological functions. Interrogation of the specificity of heparan sulfate-mediated activities demands a library of structurally defined oligosaccharides. Chemical synthesis of large heparan sulfate oligosaccharides remains challenging. We report the synthesis of oligosaccharides with different sulfation patterns and sizes from a disaccharide building block using glycosyltransferases, heparan sulfate C 5 -epimerase, and sulfotransferases. This method offers a generic approach to prepare heparan sulfate oligosaccharides possessing predictable structures. Heparan sulfate (HS)3 is a unique class of macromolecular natural product that is present in large quantities on the mammalian cell surface and in the extracellular matrix. HS participates in regulating blood coagulation, embryonic development, and the inflammatory response and assists viral/bacterial infections. It consists of a repeating disaccharide unit of glucuronic acid (GlcUA) or iduronic acid (IdoUA) and glucosamine, both capable of carrying sulfo groups (1). The sulfation pattern of HS dictates its biological activity (2, 3). Heparin, a widely used anticoagulant drug, is a specialized form of highly sulfated HS. The diverse biological functions present considerable opportunities for exploiting HS or HS-protein conjugates for developing new classes of anticancer (4), antiviral (5), and improved anticoagulant drugs (6). Furthermore, a recent worldwide outbreak of contaminated heparin underscores the needs for synthetic heparins to replace those isolated from animal tissues (7). Chemical synthesis is a powerful tool to obtain structurally defined heparin/HS oligosaccharides. The most successful example is the total synthesis of an antithrombin-binding pentasaccharide (8). This pentasaccharide is marketed under the trade name Arixtra for the treatment of venous thromboembolic disorders. However, the chemical synthesis of oligosaccharides larger than an octasaccharide is extremely difficult, especially when multiple target structures are required for biological evaluation (8). An enzyme-based method offers a promising alternative approach to synthesize HS.The HS biosynthetic pathway involves multiple enzymes, including HS polymerase, epimerase, and sulfotransferases ( Fig. 1). HS polymerase is responsible for building the polysaccharide backbone, containing the repeating unit of -GlcUA-GlcNAc-. The backbone is then modified by N-deacetylase/N-sulfotransferase (having two separate domains exhibiting the activity of N-deacetylase and N-sulfotransferase, respectively), C 5 -epimerase (C 5 -epi, converting GlcUA to IdoUA), 2-O-sulfotransferase (2-OST), 6-O-sulfotransferase (6-OST) and 3-O-sulfotransferase (3-OST) to produce the fully elaborated HS. With the exception of HS polymerase, all of these biosynthetic enzymes have been expressed at high levels in Escherichia coli (1), permitting easy access to an abundance of enzymes. Using HS sulfotransferases and C 5 -epi, we previously developed a method ...

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Section: Substratesmentioning

confidence: 99%

Chemoenzymatic Design of Heparan Sulfate Oligosaccharides*

Liu

Chen

et al. 2010

Journal of Biological Chemistry

148

193

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“…Due to their low molecular weight, oligosaccharides need to be modified with an anchoring tail such as hydrophobic chains (Fukui et al, 2002;Fazio et al, 2002;Wang et al, 2002), fluorous tags (Jaipuri et al, 2008) or macromolecules (Wang et al, 2002).…”

Section: Introductionmentioning

confidence: 99%

DNA-directed immobilisation of glycomimetics for glycoarrays application: Comparison with covalent immobilisation, and development of an on-chip IC50 measurement assay

Zhang

Pourceau

Meyer

et al. 2009

Biosensors and Bioelectronics

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“…Indeed, binding of ConA to the sevencarbon monosaccharides L-glycero-a-D-manno-and D-glycero-a-D-manno-heptose has been demonstrated. 59 Interestingly, the inner core manno-heptoses are also the primary site of interaction of surfactant protein D (SP-D), an endogenous lectin of the innate immune system, in binding to rough LPSs of Gram-negative bacteria. 60 Furthermore, the presence of the O1-antigen in K. pneumoniae LPS has been shown to signi-cantly reduce the binding efficiency of SP-D compared to rough LPS, 61 fully in line with the behaviour exhibited by ConA.…”

Section: Printed Materialsmentioning

confidence: 99%

Bacteria microarrays as sensitive tools for exploring pathogen surface epitopes and recognition by host receptors

et al. 2015

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We describe a protocol for the generation and validation of bacteria microarrays and their application to the study of specific features of the pathogen's surface and interactions with host receptors. Bacteria were directly printed on nitrocellulose-coated glass slides, using either manual or robotic arrayers, and printing quality, immobilization efficiency and stability of the arrays were rigorously controlled by screening/evaluation of compounds to identify inhibitors of host-pathogen interactions, make bacteria microarrays a useful and sensitive tool for both basic and applied research in microbiology, biomedicine and biotechnology.

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Synthesis and Quantitative Evaluation of Glycero‐D‐manno‐heptose Binding to Concanavalin A by Fluorous‐Tag Assistance

Abstract: Fooling conA? Fluorous microarrays allow not only qualitative, but also quantitative assessment of binding to show that conA can accept modifications to its usual mannose ligand at the C‐6 position and bind to bacterial seven‐carbon mannose analogues.

Cited by 96 publications

References 35 publications

Chemoenzymatic Design of Heparan Sulfate Oligosaccharides*

Chemoenzymatic Design of Heparan Sulfate Oligosaccharides*

DNA-directed immobilisation of glycomimetics for glycoarrays application: Comparison with covalent immobilisation, and development of an on-chip IC50 measurement assay

Bacteria microarrays as sensitive tools for exploring pathogen surface epitopes and recognition by host receptors

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