Glycosylation of the polypropylene membrane surface via thiol–yne click chemistry for lectin adsorption

Wang, Cang; Fan, Yan ying; Hu, Meng‐Xin; Xu, Wei; Wu, Jian; Ren, Pengfei; Xu, Zhi‐Kang

doi:10.1016/j.colsurfb.2013.04.029

Cited by 17 publications

(11 citation statements)

References 43 publications

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“…Subsequent "Click" coupling by reaction of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside thiol with the alkyne groups on poly(3-(trimethyl) propargyl methacrylate) gave a high density of carbohydrate sites. This sugar-containing polymer selectively binds Con A and resists capture of peanut agglutinin (63). These studies clearly show the promise of membrane adsorbers for lectin purification.…”

Section: Lectin Purification Using Glycosylated Membranesmentioning

confidence: 72%

Functionalizing Microporous Membranes for Protein Purification and Protein Digestion

Dong

Bruening

2015

Annual Rev. Anal. Chem.

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This review examines advances in the functionalization of microporous membranes for protein purification and the development of protease-containing membranes for controlled protein digestion prior to mass spectrometry analysis. Recent studies confirm that membranes are superior to bead-based columns for rapid protein capture, presumably because convective mass transport in membrane pores rapidly brings proteins to binding sites. Modification of porous membranes with functional polymeric films or TiO₂ nanoparticles yields materials that selectively capture species ranging from phosphopeptides to His-tagged proteins, and protein-binding capacities often exceed those of commercial beads. Thin membranes also provide a convenient framework for creating enzyme-containing reactors that afford control over residence times. With millisecond residence times, reactors with immobilized proteases limit protein digestion to increase sequence coverage in mass spectrometry analysis and facilitate elucidation of protein structures. This review emphasizes the advantages of membrane-based techniques and concludes with some challenges for their practical application.

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Section: Lectin Purification Using Glycosylated Membranesmentioning

confidence: 72%

Functionalizing Microporous Membranes for Protein Purification and Protein Digestion

Dong

Bruening

2015

Annual Rev. Anal. Chem.

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“…Mannose [61], galactose [61], glucose [63,64] (continued) Mannose [65][66][67], galactose [65], glucose [65,68], N-acetylglucosamine [65] (i) Mannose [47,69], galactose [69], complex carbohydrates [69] (j) Mannose, galactose, glucose, lactose, maltose [71] (l)…”

Section: Glycosurfaces Obtained Stepwise Using Synthetic Carbohydratementioning

confidence: 99%

“…The carbohydrate-terminated surfaces were then tested for their binding affinity of various lectins, showing good selectivity [61]. The thiol-yne reaction was also used to immobilize glucose derivatives on an alkyne-presenting microporous polypropylene membrane [63,64] and on an alkyneterminated silicon surface [107]. in the latter example, the consecutive double addition of thiol-terminated carbohydrates onto the alkyne in the thiol-yne reaction resulted in a higher surface density of carbohydrates when compared with the thiolene reaction.…”

Section: Glycosurfaces Obtained Stepwise Using Synthetic Carbohydratementioning

confidence: 99%

Carbohydrate‐Modified Gold Nanoparticles

Thygesen

Jensen

2015

Carbohydrate Nanotechnology

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Carbohydrates are a complex class of essential biomolecules that can be considered as the dark matter of the biological universe as they are greatly understudied yet omnipresent in all kingdoms of life and vital to fully understand biological processes. The structurally diverse carbohydrates are present both on the cell surface and inside cells. They decorate the cell surface to form the so-called glycocalyx, a dense and complex layer of carbohydrates unique for every type of cell or organism, and as such are key to many important biological recognition events by interacting with carbohydrate-binding proteins. Carbohydrate-protein interactions play an important role in various biological events occurring at the cell surface, such as bacterial and viral infections [1,2], cancer metastasis [3,4], and immune response [4]. The study of the interactions between carbohydrates and other biomolecules at biological surfaces

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“…The preparation of sugar‐coated membranes for the selective recognition of lectins was published in 2013 by Xu and co‐workers 41. Microporous polypropylene membranes (MPPMs) were functionalized with alkyne units through plasma treatment of the surface followed by UV‐induced graft polymerization with 3‐(trimethylsilyl)propargyl methacrylate (Scheme ).…”

Section: Metal‐free Hydrothiolation – the Free‐radical Approachmentioning

confidence: 99%

Metal‐Catalyzed and Metal‐Free Alkyne Hydrothiolation: Synthetic Aspects and Application Trends

Dondoni

Marra

2014

Eur J Org Chem

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Alkyne hydrothiolation – that is, the addition of the SH bond of a thiol across the carbon‐carbon triple bond of an unactivated alkyne – belongs to the ample class of hydrofunctionalization reactions whose main feature is their occurrence with total atom economy. Hence this reaction is emerging as a valuable tool for the preparation of sulfur‐containing compounds such as vinyl thioethers, which are of interest for their own biological properties and for their use as intermediates in total synthesis. Thus, the first part of this review deals with the various efforts directed towards the preparation of vinyl thioethers in a regio‐ and diastereoselective manner by metal‐catalyzed approaches in recent years. The number of methods employed, with use of a variety of catalysts and reaction conditions, allow the synthesis of vinyl thioethers to be carried out with high efficiency and selectivity. The second part of the article is based on the use of the photoinduced free‐radical approach to hydrothiolation, which allows the introduction of two thiol fragments across the carbon‐carbon triple bond, thereby leading to the formation of dithioethers. This approach turned out to be especially useful as a ligation tool for the installation of densely functionalized arrays on various scaffolds and complex biomolecular systems. Concluding remarks emphasize the role of the photoinduced free‐radical strategy as a complementary tool to copper‐catalyzed azide‐alkyne cycloaddition.

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Glycosylation of the polypropylene membrane surface via thiol–yne click chemistry for lectin adsorption

Cited by 17 publications

References 43 publications

Functionalizing Microporous Membranes for Protein Purification and Protein Digestion

Functionalizing Microporous Membranes for Protein Purification and Protein Digestion

Carbohydrate‐Modified Gold Nanoparticles

Metal‐Catalyzed and Metal‐Free Alkyne Hydrothiolation: Synthetic Aspects and Application Trends

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