Ultraviolet photodissociation of chromophore‐labeled oligosaccharides via reductive amination and hydrazide conjugation

Ko, Byoung Joon; Brodbelt, Jennifer S.

doi:10.1002/jms.1901

Cited by 17 publications

(21 citation statements)

References 59 publications

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“…59 In addition to the attachment of chromophores to oligosaccharides or glycans by reductive amination, the chromophores were attached to the reducing ends via hydrazide-conjugation, as demonstrated for fucopentaoses (LNFPs) and lacto-N-difucohexaoses (LNDFHs). 179 The two methods of attaching chromophores to oligosaccharides generated different series of cross-ring cleavages upon UVPD and CID. UVPD of hydrazide-conjugated oligosaccharide resulted in 2,4 A-type cross-ring cleavage ions, whereas the aminated oligosaccharides predominantly produced 0,1 A-type ions.…”

Section: Applications Of Ultraviolet Photodissociation For Biologimentioning

confidence: 99%

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Photodissociation mass spectrometry: new tools for characterization of biological molecules

2014

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Photodissociation mass spectrometry combines the ability to activate and fragment ions using photons with the sensitive detection of the resulting product ions by mass spectrometry. The resulting combination affords a versatile tool for characterization of biological molecules. The scope and breadth of photodissociation mass spectrometry have increased substantially over the past decade as new research groups have entered the field and developed a number of innovative applications that illustrate the ability of photodissociation to produce rich fragmentation patterns, to cleave bonds selectively, and to target specific molecules based on incorporation of chromophores. This review focuses on many of the key developments in photodissociation mass spectrometry over the past decade with a particular emphasis on its applications to biological molecules.

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Section: Applications Of Ultraviolet Photodissociation For Biologimentioning

confidence: 99%

“…UVPD of hydrazide-conjugated oligosaccharide resulted in 2,4 A-type cross-ring cleavage ions, whereas the aminated oligosaccharides predominantly produced 0,1 A-type ions. 179 …”

Section: Applications Of Ultraviolet Photodissociation For Biologimentioning

confidence: 99%

Photodissociation mass spectrometry: new tools for characterization of biological molecules

2014

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“…Recently, Ko and Brodbelt () compared the fragmentation patterns of hydrazide‐conjugated and reductively aminated oligosaccharides under CID (collisionally induced dissociation) and UVPD (ultraviolet photodissociation) in a quadrupole ion trap. The hydrazide conjugation procedure proved again to be an easy reaction (Table ).…”

Section: Structural Analysis Of Hydrazone Labeled Saccharidesmentioning

confidence: 99%

The usefulness of hydrazine derivatives for mass spectrometric analysis of carbohydrates

Lattová

Perreault

2013

Mass Spectrometry Reviews

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Over the last years, extensive studies have evaluated glycans from different biological samples and validated the importance of glycosylation as one of the most important post-translational modifications of proteins. Although a number of new methods for carbohydrate analysis have been published and there has been significant progress in their identification, the development of new approaches to study these biomolecules and understand their role in living systems are still vivid challenges that intrigue glycobiologists. In the last decade, the success in analyses of oligosaccharides has been driven mainly by the development of innovative, highly sensitive mass spectrometry techniques. For enhanced mass spectrometry detection, carbohydrate molecules are often derivatized. Besides, the type of labeling can influence the fragmentation pattern and make the structural analysis less complicated. In this regard, in 2003 we introduced the low scale, simple non-reductive tagging of glycans employing phenylhydrazine (PHN) as the derivatizing reagent. PHN-labeled glycans showed increased detection and as reported previously they can be analyzed by HPLC, ESI, or MALDI immediately after derivatization. Under tandem mass spectrometry conditions, PHN-derivatives produced useful data for the structural elucidation of oligosaccharides. This approach of analysis has helped to reveal new isomeric structures for glycans of known/unknown composition and has been successfully applied for the profiling of N-glycans obtained from serum samples and cancer cells. The efficacy of this labeling has also been evaluated for different substituted hydrazine reagents. This review summarizes all types of reducing-end labeling based on hydrazone-linkage that have been used for mass spectrometric analyses of oligosaccharides. This review is also aimed at correcting some past misconceptions or interpretations reported in the literature.

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“…40 mg of NaCNBH 3 was added, and the reaction was allowed to proceed for 18 h to 24 h at room temperature. 28,29,41 The solution was placed in a 12 K MWCO dialysis membrane and dialyzed against 800 mL of DMSO for at least 10 h. The dialysis medium was changed to 4 L of DI H 2 O, and dialysis was continued for 24 h against at least three changes of water (Note: after changing the medium, some dialysis membranes swelled to the point of bursting. Thus it is important to carefully observe them and re-distribute the contents into new membranes if this occurs).…”

Section: Coupling Of Oxidized Particles To Amcmentioning

confidence: 99%

“…This procedure is frequently used in the literature to couple AMC to sugars in order to use it as a°uorescent tag for mass spectroscopy applications. 28,29,41 Throughout the synthesis process, particle size measurements were taken to observe and verify the e®ect of subsequent modi¯cations. As can be seen in Table 1, a large size increase occurs after functionalization with dextran, which is expected given that the hydrophilic dextran chains will tend to form a di®use corona around the surface of each particle, increasing its hydrodynamic size.…”

Section: Synthesismentioning

confidence: 99%

Light-Induced Aggregation of Nanoparticles Functionalized With 7-Amino-4-Methylcoumarin

Rosen

Jones

2012

Nano LIFE

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Herein, we report on the modi¯cation of silica nanoparticles with the molecule 7-amino-4-methylcoumarin (AMC) via a hydrophilic dextran linker using reductive amination chemistry. The AMC-functionalized nanoparticles were shown to aggregate in response to irradiation by 350 nm UV light. The aggregation of the particles was studied using dynamic light scattering, UV-VIS spectroscopy, and transmission electron microscopy. The synthesis method described herein utilizes a classic reductive amination reaction, which can potentially be transferred to a variety of di®erent types of nanoparticles. Particles displaying this behavior have many potential applications in the¯eld of nanomedicine, as they can potentially allow one to modulate the particle size of a nanoparticle formulation after administration to the body. The AMC-functionalized particles studied in this report serve as a convincing proof-of-concept for synthesizing light-responsive nanoparticles.

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Ultraviolet photodissociation of chromophore‐labeled oligosaccharides via reductive amination and hydrazide conjugation

Cited by 17 publications

References 59 publications

Photodissociation mass spectrometry: new tools for characterization of biological molecules

Photodissociation mass spectrometry: new tools for characterization of biological molecules

The usefulness of hydrazine derivatives for mass spectrometric analysis of carbohydrates

Light-Induced Aggregation of Nanoparticles Functionalized With 7-Amino-4-Methylcoumarin

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