Click novel glycosyl amino acid hydrophilic interaction chromatography stationary phase and its application in enrichment of glycopeptides

Huang, Hongxue; Guo, Hongyue; Xue, Meiyun; Liu, Yajing; Yang, Jinjin; Liang, Xinmiao; Chu, Changhu

doi:10.1016/j.talanta.2011.06.055

Cited by 21 publications

(20 citation statements)

References 54 publications

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“…17,18,[25][26][27][28] It is noticeable that a regioselective 1,2,3-triazole ring is formed in this reaction. In previous work, we have described a simple hydrophilic stationary phase bearing a 1,2,3-triazole ring and a hydroxymethyl group in 4-position of this ring, which could be used for separating polar compounds under HILIC mode as well as separating anions under IC mode.…”

Section: Introductionmentioning

confidence: 99%

Silica based click amino stationary phase for ion chromatography and hydrophilic interaction liquid chromatography

Liu

Yang

et al. 2012

Analyst

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A silica based amino stationary phase was prepared by immobilization of propargylamine on azide-silica via click chemistry. This readily prepared click amino stationary phase demonstrated good selectivity in separation of common inorganic anions under ion chromatography (IC) mode, and the triazole ring in combination with free amino group was observed to play a major role for separation of the anions examined. On the other hand, the stationary phase also showed good hydrophilic interaction liquid chromatography (HILIC) properties in the separation of polar compounds including nucleosides, organic acids and bases. The retention mechanism was found to match well the typical HILIC retention.

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Section: Introductionmentioning

confidence: 99%

Silica based click amino stationary phase for ion chromatography and hydrophilic interaction liquid chromatography

Liu

Yang

et al. 2012

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“…In some cases, the key azido intermediates were synthesized from transferring the amino group to corresponding azido group by using a diazotransfer reagent under mild conditions. [35][36][37] By the same strategy, the azido lysine was prepared from commercially available L-Boc lysine. The click between the terminal alkyne-silica gel and azido lysine in the presence of Cu(I) catalyst afforded lysine functionalized stationary phase, which was packed as the column.…”

Section: Resultsmentioning

confidence: 99%

“…In our previous work, we have prepared several functionalized stationary phases for separation of highly polar compounds and glycopeptides enrichment in HILIC mode, for the separation of complex samples with 2-dimensional LC. [35][36][37] In these cases, an efficient, inexpensive and shelf-stable diazotransfer reagent (imidazole-1-sulfonyl azide hydrochloride) was used to transfer the amino groups to corresponding azido group under very mild conditions, 38 which allowed access to obtain key multifunctional azide intermediates. All these stationary phases prepared by click chemistry showed good chromatographic characteristics in the separation of polar compounds and complex samples with 2-dimensional LC, as well as in glycopeptides enrichment.…”

Section: -11mentioning

confidence: 99%

A novel silica based click lysine anion exchanger for ion exchange chromatography

Guo

Chu

et al. 2011

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Ion chromatography (IC) is one of the most powerful analysis technologies for the determination of charged compounds. A novel click lysine stationary phase was prepared via Cu(I) catalyzed alkyneazide 1,3-dipolar cycloaddition (CuAAC) and applied to the analysis of inorganic ions. The chromatographic evaluation demonstrated good performance (e.g. the plate number of thiocyanate is $50 000 plates m À1) and effective separation ability for the common inorganic anions with aqueous Na 2 SO 4 eluent. The separation mechanism was observed to be mainly dominated by ion exchange interaction. The retention of these analytes is highly dependent on the pH value of eluent. Compared with the lysine stationary phase prepared via the conventional manner, the click lysine exchanger demonstrated shorter retention time and better ion separation characteristics under the same chromatographic conditions, which is a great advantage for rapid separation and analysis of inorganic ions.

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“…These columns show excellent separation selectivity for the separation of polar compounds (nucleosides, sugar, and sugar derivatives). The same CuAAc chemistry has been used to immobilize glycosyl phenyl glycine on silica beads . The click reaction was achieved at room temperature during five days (which is not negligible).…”

Section: “Clicked” Stationary Phases and Their Applications In Varioumentioning

confidence: 99%

Is click chemistry attractive for separation sciences?

Marechal

El-Debs

Dugas

et al. 2013

J of Separation Science

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Trends in LC focus on dedicated separation developments spanning different fields of applications ranging from sample preparation to miniaturization. Chromatographic performances result from the porous media, its implantation inside the "column," and its surface functionalization. Because molecular interactions govern chromatographic phenomena, surface functionalization is still a hot research topic. Besides standard approaches for surface functionalization, the use of new surface chemistry reactions opens new perspectives. Click chemistry belongs to this new class of chemical reactions, characterized by its specificity, compatibility with aqueous media, and high reaction yields. In this frame, we review the use of click chemistry reactions in chromatographic sciences. In a first part, we present click chemistry with a specific focus on its implementation in stationary phases. The use of these new clicked materials is detailed and discussed with respect to the chromatographic mode.

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Click novel glycosyl amino acid hydrophilic interaction chromatography stationary phase and its application in enrichment of glycopeptides

Cited by 21 publications

References 54 publications

Silica based click amino stationary phase for ion chromatography and hydrophilic interaction liquid chromatography

Silica based click amino stationary phase for ion chromatography and hydrophilic interaction liquid chromatography

A novel silica based click lysine anion exchanger for ion exchange chromatography

Is click chemistry attractive for separation sciences?

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