Glycosyl Azides – An Alternative Way to Disaccharides

Bojarová, Pavla; Petrásková, Lucie; Ferrandi, Erica Elisa; Monti, Daniela; Kuzma, Marek; Simerská, Pavla; Křen, Vladimı́r

doi:10.1002/adsc.200700028

Cited by 31 publications

(15 citation statements)

References 30 publications

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“…This by-product was formed as a result of partial cleavage and transfer of azido acceptor 4 , which could not be completely abolished under any conditions tested. Glycosidases are known to cleave and transfer glycosyl using glycosyl azide as a donor [ 38 , 46 ], though at a much lower rate than with aryl glycosides. Due to its high structural similarity, this by-product was separable by gel chromatography only partially, which resulted in a lower preparative yield of 7 compared to 6 .…”

Section: Resultsmentioning

confidence: 99%

Biocompatible glyconanomaterials based on HPMA-copolymer for specific targeting of galectin-3

et al. 2018

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BackgroundGalectin-3 (Gal-3) is a promising target in cancer therapy with a high therapeutic potential due to its abundant localization within the tumor tissue and its involvement in tumor development and proliferation. Potential clinical application of Gal-3-targeted inhibitors is often complicated by their insufficient selectivity or low biocompatibility. Nanomaterials based on N-(2-hydroxypropyl)methacrylamide (HPMA) nanocarrier are attractive for in vivo application due to their good water solubility and lack of toxicity and immunogenicity. Their conjugation with tailored carbohydrate ligands can yield specific glyconanomaterials applicable for targeting biomedicinally relevant lectins like Gal-3.ResultsIn the present study we describe the synthesis and the structure-affinity relationship study of novel Gal-3-targeted glyconanomaterials, based on hydrophilic HPMA nanocarriers. HPMA nanocarriers decorated with varying amounts of Gal-3 specific epitope GalNAcβ1,4GlcNAc (LacdiNAc) were analyzed in a competitive ELISA-type assay and their binding kinetics was described by surface plasmon resonance. We showed the impact of various linker types and epitope distribution on the binding affinity to Gal-3. The synthesis of specific functionalized LacdiNAc epitopes was accomplished under the catalysis by mutant β-N-acetylhexosaminidases. The glycans were conjugated to statistic HPMA copolymer precursors through diverse linkers in a defined pattern and density using Cu(I)-catalyzed azide–alkyne cycloaddition. The resulting water-soluble and structurally flexible synthetic glyconanomaterials exhibited affinity to Gal-3 in low μM range.ConclusionsThe results of this study reveal the relation between the linker structure, glycan distribution and the affinity of the glycopolymer nanomaterial to Gal-3. They pave the way to specific biomedicinal glyconanomaterials that target Gal-3 as a therapeutic goal in cancerogenesis and other disorders.Electronic supplementary materialThe online version of this article (10.1186/s12951-018-0399-1) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Biocompatible glyconanomaterials based on HPMA-copolymer for specific targeting of galectin-3

et al. 2018

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“…[76] Notably, the a-fucosynthases were able to process bl-fucosyl azides as glycosyl donors, instead of the generally used fluorides. The concept of glycosyl azides as donors for glycosidases was previously applied with a range of natural glycosidases [81,82] and also with thioglycoligases. [83] The thioglycoligase enzymes, together with double mutant thioglycosynthases, [84] are the first biocatalysts readily synthesizing thioglycosides with good yields, up to 50 %.…”

Section: Glycoside Hydrolasesmentioning

confidence: 99%

Enzymatic Glycosylation of Small Molecules: Challenging Substrates Require Tailored Catalysts

Desmet

Soetaert

Bojarová

et al. 2012

Chemistry A European J

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194

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Glycosylation can significantly improve the physicochemical and biological properties of small molecules like vitamins, antibiotics, flavors, and fragrances. The chemical synthesis of glycosides is, however, far from trivial and involves multistep routes that generate lots of waste. In this review, biocatalytic alternatives are presented that offer both stricter specificities and higher yields. The advantages and disadvantages of different enzyme classes are discussed and illustrated with a number of recent examples. Progress in the field of enzyme engineering and screening are expected to result in new applications of biocatalytic glycosylation reactions in various industrial sectors.

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“…Besides these, glycosyl fluoride donors, which have poor stability in water, have also been used with glycosynthases. For β-glucosidases and β-galactosidases, glycosyl azides are considered to be good alternative substrates [73]. Different chain length alcohols, mostly primary alcohols, have been used as acceptors for the synthesis of AGs (Tables 2 and 3).…”

Section: Nature Of the Substratementioning

confidence: 99%

β-Glycosidases: An alternative enzyme based method for synthesis of alkyl-glycosides

Rather

Mishra

2013

Sustain Chem Process

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Alkyl-glycosides and-polyglycosides are environment friendly, non-ionic surfactants with favourable properties like biodegradability and chemical stability. These are extensively used in personal care products, pharmaceutical preparations and membrane protein research. Commercial production of these surfactants is carried out in multiple steps through Fischer glycosylation reactions under extreme conditions in the presence of toxic catalysts. β-glycosidases provide an alternative enzymatic method for their synthesis as these are easily available from microbial systems and exhibit broad substrate specificity and high stereo-selectivity. This review highlights the recent progress in glycosidase catalyzed synthesis of alkyl-glycosides. Several reaction parameters that affect the overall reaction kinetics, such as, water activity, nature of the glycosyl donor, pH of the reaction medium, reaction time, temperature and source of enzyme are discussed. Strategies available to enhance the yield, including two-phase solvent systems and immobilization are described. Current challenges and future prospects in the biological routes of synthesis are also reviewed.

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Glycosyl Azides – An Alternative Way to Disaccharides

Cited by 31 publications

References 30 publications

Biocompatible glyconanomaterials based on HPMA-copolymer for specific targeting of galectin-3

Biocompatible glyconanomaterials based on HPMA-copolymer for specific targeting of galectin-3

Enzymatic Glycosylation of Small Molecules: Challenging Substrates Require Tailored Catalysts

β-Glycosidases: An alternative enzyme based method for synthesis of alkyl-glycosides

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