N-Hexyl-4-aminobutyl glycosides for investigating structures and biological functions of carbohydrates

Suzuki, Katsuhiko; Tobe, Akifumi; Adachi, Shin; Daikoku, Shusaku; Hasegawa, Yasuko; Shioiri, Yuki; Kobayashi, Mariko; Kanie, Osamu

doi:10.1039/b909556j

Cited by 12 publications

(7 citation statements)

References 32 publications

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“…Further investigation on glycosphingolipids obtained from cultured cells is in progress to reveal the regulatory mechanism of glycan synthesis in our laboratory. 23,24 We envision that the system will become an important platform in glycomics research.…”

Section: Discussionmentioning

confidence: 99%

Fluorescence-monitored zero dead-volume nanoLC-microESI-QIT-TOF MS for analysis of fluorescently tagged glycosphingolipids

Daikoku

Ono

Ohtake

et al. 2011

Analyst

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An analysis of the glycan processing event is of particular importance to understand the nontemplate dependent synthetic mechanism of the multiple glycosylation reactions taking place in the Golgi apparatus in connection with the post-translational modification of biomolecules. In our efforts to address the issue, we constructed an analysis platform using nano-liquid chromatography (LC), which also worked as a spray tip, with an optical-fiber-based blue (470 nm) light emitting diode (LED)-induced fluorescence (520 nm) detector coupled with a microelectrospray ionization (ESI)-quadrupole ion trap (QIT)-time of flight (TOF) mass spectrometer (MS). This system was designed to enable both quantitative and qualitative analyses of fluorescently tagged molecules such as BODIPY-tagged lactosylceramide. Owing to the zero dead volume after LC separation, an extremely high sensitivity was achieved for the quantitative analysis (260 amol). It was also shown that a simultaneous online structural analysis based on MS could be achieved for the same quantity of analyte. To further demonstrate its potential, an enzymatic reaction of fluorescently tagged lactosylceramide using sialyltransferase was carried out, and the conversion yield was obtained on the basis of fluorescence detection. In addition, the structural details of a product, sialyl lactosylceramide, were obtained by MS and MS/MS analyses.

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Section: Discussionmentioning

confidence: 99%

Fluorescence-monitored zero dead-volume nanoLC-microESI-QIT-TOF MS for analysis of fluorescently tagged glycosphingolipids

Daikoku

Ono

Ohtake

et al. 2011

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“…When this conjugate was fed to a PC-12D cell culture, it was possible to visualize specific Golgi vesicles through fluorescence confocal imaging. Fluorescently labelled glycans were also shown to be useful in tracking the internalization and cell activation of inositol phosphate glycans [51], to profile cytoplasmic peptide:Nglycanase [52] or other glycosidases [53], and cell targeting and uptake of glycans [54][55][56].…”

Section: Fluorescently Labelled Glycans For Intracellular Applicationsmentioning

confidence: 98%

Fluorescently labelled glycans and their applications

Yan

Yalagala

Yan³

2015

Glycoconj J

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This review summarises the literature on the synthesis and applications of fluorescently labelled carbohydrates. Due to the sensitivity of fluorescent detection, this approach provides a useful tool to study processes involving glycans. A few general categories of labelling are presented, in situ labelling of carbohydrates with fluorophores, fluorescently labelled glycolipids, fluorogenic glycans, pre-formed fluorescent glycans for intracellular applications, glycan-decorated fluorescent polymers, fluorescent glyconanoparticles, and other functional fluorescent glycans.

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“…Taking advantage of synthetic chemistry, it was reported that the carbohydrate C-ions could be generated stereo-specifically in gas phase, from the corresponding 4-aminobutylglycosides [67,68]. This particular glycoside with an amino group could also be utilized in preparing the required conjugates for biological investigations [69].…”

Section: Suitable Ion Species For the Structural Analysismentioning

confidence: 99%

Addressing the glycan complexity by using mass spectrometry: In the pursuit of decoding glycologic

Kanie¹,

Kanie²

2017

Bio Chem Comp

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Biomolecules often contain carbohydrates. Such molecules, namely glycoconjugates, play central roles in cell adhesion, tumor migration, and attachment of pathogens. The conjugation of "natural products" with glycans is not a template-dependent process but is achieved by multiple enzymatic reactions. Because of the nature of the synthetic process, glycans exist as a complex mixture creating a glycoform and thus, the analysis becomes inevitably difficult. Mass spectrometry is one of the most informative, and thus important, tools for the structural analysis of glycans. The obvious advantage of mass spectrometry is the high sensitivity at low femtomole detection levels. A variety of ions can be obtained depending on the adducted cationic species. In order to obtain sequential information, the gas-phase dissociation reaction is used. Among the various techniques, collision-induced dissociation (CID) has been frequently used in the past. Although the technique is proven useful, there are cases that normal CID process is not suitable. This review highlights an emerging technique that focuses on the activation-energy difference between the isomeric glycans, and will complement the current methods. Furthermore, the possible source and the methodology for obtaining useful structural information are discussed.

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N-Hexyl-4-aminobutyl glycosides for investigating structures and biological functions of carbohydrates

Cited by 12 publications

References 32 publications

Fluorescence-monitored zero dead-volume nanoLC-microESI-QIT-TOF MS for analysis of fluorescently tagged glycosphingolipids

Fluorescence-monitored zero dead-volume nanoLC-microESI-QIT-TOF MS for analysis of fluorescently tagged glycosphingolipids

Fluorescently labelled glycans and their applications

Addressing the glycan complexity by using mass spectrometry: In the pursuit of decoding glycologic

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