Design and Facile Synthesis of Neoglycolipids as Lactosylceramide Mimetics and Their Transformation into Glycoliposomes

Harada, Yoichiro; Murata, Takeomi; Totani, Kiichiro; Kajimoto, Tetsuya; Masum, Shah Md.; Tamba, Yukihiro; Yamazaki, Masahito; Usui, Taichi

doi:10.1271/bbb.69.166

Cited by 23 publications

(12 citation statements)

References 27 publications

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“…In the absence of the linker, the reaction did not progress (data not shown). The use of HMG as a linker has also been reported in a reaction using a different enzyme system (Harada et al 2005). This sugar fatty acid ester synthesis method using transglycosylation should aid in the development of emulsifiers or surfactants with various functions.…”

Section: Resultsmentioning

confidence: 94%

Synthesis of sugar fatty acid esters using a β-xylosidase from Aspergillus awamori for transxylosylation

2011

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Aspergillus awamori K4 β-xylosidase has broad acceptor specificity. It has been used to synthesize a sugar fatty acid ester via its transxylosylation activity. One xylosyl residue was initially transferred to hexamethylene glycol as a linker with a yield of 0.36 g/g xylobiose. Linoleic acid was subsequently linked to one terminal hydroxyl side of the transfer product hydroxyhexyl xyloside through an esterification reaction catalyzed by a lipase. The synthesis of hexyl linoleoyl xyloside was confirmed by TOF-MS analysis. The binding with a linker improved the esterification reaction because of the hydrophobic hexamethylene chain and also prevented steric hindrance by the xylosyl residue. This sugar fatty acid ester synthesis method using transglycosylation should facilitate the production of emulsifiers or surfactants with various functions.

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Section: Resultsmentioning

confidence: 94%

Synthesis of sugar fatty acid esters using a β-xylosidase from Aspergillus awamori for transxylosylation

2011

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“…Principal synthetic approaches to multivalent aggregates include: i) direct self-assembly of appropriate glycosylated amphiphilic molecules, for example based on polyethylene glycol, peptides and/or alkyl linkers with long carbon chains; ii) incorporation of glycosylated amphiphilic molecules with suitable lipid matrices at optimal molar ratios (usually ∼5-10%); and iii) functionalization of pre-formed liposomes or micelles with specific carbohydrate structures (Harada et al, 2005). Owing to their relatively straightforward fabrication, liposome- or micelle- based glyconanomaterials have continuously been developed for biomedical applications, and also as tools for biosensing (Assali et al, 2013; Hildebrand et al, 2002; Mahon et al, 2010b).…”

Section: Synthesis Of Glyconanomaterialsmentioning

confidence: 99%

Glyconanomaterials for biosensing applications

Hao

Neranon

Ramström

et al. 2016

Biosensors and Bioelectronics

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Nanomaterials constitute a class of structures that have unique physiochemical properties and are excellent scaffolds for presenting carbohydrates, important biomolecules that mediate a wide variety of important biological events. The fabrication of carbohydrate-presenting nanomaterials, glyconanomaterials, is of high interest and utility, combining the features of nanoscale objects with biomolecular recognition. The structures can also produce strong multivalent effects, where the nanomaterial scaffold greatly enhances the relatively weak affinities of single carbohydrate ligands to the corresponding receptors, and effectively amplifies the carbohydrate-mediated interactions. Glyconanomaterials are thus an appealing platform for biosensing applications. In this review, we discuss the chemistry for conjugation of carbohydrates to nanomaterials, summarize strategies, and tabulate examples of applying glyconanomaterials in in vitro and in vivo sensing applications of proteins, microbes, and cells. The limitations and future perspectives of these emerging glyconanomaterials sensing systems are furthermore discussed.

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“…One major glycoliposome class is that of glycolipids with phosphate linkages. Liposomes containing, for example, lactosyl‐ and N ‐acetyllactosaminyl‐phospholipids (compounds 43 and 44 , Scheme ) have been prepared as mimics of the naturally occurring lactosylceramide glycolipids and used to study the comparative lectin‐binding abilities of all three glycoliposomal contracts 103. The lectin‐binding assay was performed either with FITC‐labelled Ricinus communis agglutinin or with glycoliposomes immobilised on microtitre plates, and it was determined that Lac‐DPPE glycolipid 44 showed a lower binding affinity than the other two liposomes.…”

Section: Glycoliposomesmentioning

confidence: 99%

Enhanced transient recombinant protein production in CHO cells through the co‐transfection of the product gene withBcl‐x_L

Zustiak

Xie

et al. 2014

Biotechnology Journal

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Transient gene expression is gaining popularity as a method to rapidly produce recombinant proteins in mammalian cells. Although significant improvements have been made, in terms of expression, more improvements are needed to compete with the yields achievable in stable gene expression. Much progress has come from optimization of transfection media and parameters, as well as altering culturing conditions to enhance productivity. Recent studies have included using cell lines engineered for apoptosis resistance through the constitutive expression of an anti-apoptotic protein, Bcl-xL. In this study we examine an alternative method of using the benefits of anti-apoptotic gene expression to enhance the transient expression of biotherapeutics, namely, through the co-transfection of bcl-xL and the product-coding gene. CHO-S cells were co-transfected with the product-coding gene and a vector containing Bcl-xL using polyethylenimine. Cells co-transfected with Bcl-xL showed reduced levels of apoptosis, increased specific productivity, and an overall increase in product yield of approximately 100%. Similar results were produced by employing another anti-apoptotic protein, Bcl-2 delta in CHO cells, or through the co-transfection with bcl-xL using HEK-293E cells. This work provides an alternative method for increasing yields of therapeutic proteins in TGE applications without generating a prior stable cell line and subsequent screening which are both time and resource consuming.

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Design and Facile Synthesis of Neoglycolipids as Lactosylceramide Mimetics and Their Transformation into Glycoliposomes

Cited by 23 publications

References 27 publications

Synthesis of sugar fatty acid esters using a β-xylosidase from Aspergillus awamori for transxylosylation

Synthesis of sugar fatty acid esters using a β-xylosidase from Aspergillus awamori for transxylosylation

Glyconanomaterials for biosensing applications

Enhanced transient recombinant protein production in CHO cells through the co‐transfection of the product gene withBcl‐x_L

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Design and Facile Synthesis of Neoglycolipids as Lactosylceramide Mimetics and Their Transformation into Glycoliposomes

Cited by 23 publications

References 27 publications

Synthesis of sugar fatty acid esters using a β-xylosidase from Aspergillus awamori for transxylosylation

Synthesis of sugar fatty acid esters using a β-xylosidase from Aspergillus awamori for transxylosylation

Glyconanomaterials for biosensing applications

Enhanced transient recombinant protein production in CHO cells through the co‐transfection of the product gene withBcl‐xL

Contact Info

Product

Resources

About

Enhanced transient recombinant protein production in CHO cells through the co‐transfection of the product gene withBcl‐x_L