Synthesis and characterization of novel fluorescent N-glycoconjugates

Esteves, Ana Paula; Rodrigues, Lígia M.; Silva, Marília E.; Gupta, Sheifali; Oliveira‐Campos, Ana M. F.; Machalický, Oldřich; Mendonça, António

doi:10.1016/j.tet.2005.07.006

Cited by 26 publications

(18 citation statements)

References 27 publications

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“…Moreover, the synthesis and the evaluation of the biological activities of different N-alkyl glucosylamines were of interest since the association of the amino compounds with a carbohydrate not only facilitates the interaction with microorganisms but also increases the compound's solubility in water, and enhances the biological activity as well. 4,[13][14][15] These compounds are advantageous since they are easily synthesized from renewable resources such as sugars.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of N-alkyl-β-d-glucosylamines on the growth of two wood fungi, Coriolus versicolor and Poria placenta

Muhizi

Coma

Grelier

2008

Carbohydrate Research

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Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of N-alkyl-β-d-glucosylamines on the growth of two wood fungi, Coriolus versicolor and Poria placenta

Muhizi

Coma

Grelier

2008

Carbohydrate Research

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“…Glycosyl azides have been widely recognized as important classes of carbohydrate derivatives due to the versatile reactivities of the azido group (77,78). Notably, peracetylated a-glycosyl bromide 1n in PEG 400 provided the S N 2 product peracetylated b-glycosyl azide 2n in quantitative yield and its b-D-gluco configuration was confirmed by the l H NMR spectrum, in which the signal for the anomeric proton appeared as a doublet at 4.64 ppm (J 1,2 0 8.8 Hz) (41,79). In addition, 6-iodo-6-deoxy-1,2:3, 4-di-O-isopropylidene-a-D-galactose 1o can also yield 6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-a-D-galactose 2o within 30 min.There was no reaction in the absence of PEG 400.…”

Section: Resultsmentioning

confidence: 89%

PEG 400 promoted nucleophilic substitution reaction of halides into organic azides under mild conditions

Zeng

Tian

Shao

2011

Green Chemistry Letters and Reviews

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Polyethylene glycol 400 (PEG 400) has been demonstrated as an efficient and eco-friendly reaction medium for the preparation of organic azides from structurally diverse halides by nucleophilic substitution reaction with NaN 3 under mild conditions. The advantages of this protocol are: operational simplicity, environmental safety, broad substrate scope, excellent functional group tolerance, and short reaction time. The PEG 400 can be recovered and reused.

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“…15, 34–36 The incorporation of a biotin tag can be used for lectin-sugar interaction studies using avidin affinity chromatography and/or avidin coated micro-well plates. 37, 38 Functionalization of N-linked glycans with 5-carboxyfluorescein introduces a fluorescent chromophore 9 that can be used in many types of fluorescence experiments. On-resin labeling was achieved by using 10 equivalents of each of the previously specified functional labels, 10 equivalents of DEPBT, and 5 equivalents of DIEA.…”

Section: Resultsmentioning

confidence: 99%

Versatile on-resin synthesis of high mannose glycosylated asparagine with functional handles

Chen¹,

Pawlicki²,

Tolbert³

2014

Carbohydrate Research

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Here we present a synthetic route for solid phase synthesis of N-linked glycoconjugates containing high mannose oligosaccharides which allows the incorporation of useful functional handles on the N-terminus of asparagine. In this strategy, the C-terminus of an Fmoc protected aspartic acid residue is first attached to a solid phase support. The side chain of aspartic acid is protected by a 2-phenylisopropyl protecting group, which allows selective deprotection for the introduction of glycosylation. By using a convergent on-resin glycosylamine coupling strategy, an N-glycosidic linkage is successfully formed on the free side chain of the resin bound aspartic acid with a large high mannose oligosaccharide, Man8GlcNAc2, to yield N-linked high mannose glycosylated asparagine. The use of on-resin glycosylamine coupling provides excellent glycosylation yield, can be applied to couple other types of oligosaccharides, and also makes it possible to recover excess oligosaccharides conveniently after the on-resin coupling reaction. Useful functional handles including an alkene (p-vinylbenzoic acid), an alkyne (4-pentynoic acid), biotin, and 5-carboxyfluorescein are then conjugated onto the N-terminal amine of asparagine on-resin after the removal of the Fmoc protecting group. In this way, useful functional handles are introduced onto the glycosylated asparagine while maintaining the structural integrity of the reducing end of the oligosaccharide. The asparagine side chain also serves as a linker between the glycan and the functional group and preserves the native presentation of N-linked glycan which may aid in biochemical and structural studies. As an example of a biochemical study using functionalized high mannose glycosylated asparagine, a fluorescence polarization assay has been utilized to study the binding of the lectin Concanavalin A (ConA) using 5-carboxyfluorescein labeled high mannose glycosylated asparagine.

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Synthesis and characterization of novel fluorescent N-glycoconjugates

Cited by 26 publications

References 27 publications

Synthesis and evaluation of N-alkyl-β-d-glucosylamines on the growth of two wood fungi, Coriolus versicolor and Poria placenta

Synthesis and evaluation of N-alkyl-β-d-glucosylamines on the growth of two wood fungi, Coriolus versicolor and Poria placenta

PEG 400 promoted nucleophilic substitution reaction of halides into organic azides under mild conditions

Versatile on-resin synthesis of high mannose glycosylated asparagine with functional handles

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