Simple Approach for De Novo Structural Identification of Mannose Trisaccharides

Hsu, Hsu Chen; Liew, Chia Yen; Huang, Shih-Pei; Tsai, Shang‐Ting; Ni, Chi-Kung

doi:10.1007/s13361-017-1850-5

Cited by 42 publications

(67 citation statements)

References 32 publications

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“…In this study, the CID spectrum of each disaccharide anomer was measured immediately after the separation of anomers by HPLC. Our previous study on hexose disaccharide sodium adducts demonstrated that both the anomeric configurations of the glycosidic bond and the sugar at the reducing end could be determined by using the relative intensities of glycosidic bond cleavage, dehydration, and cross‐ring dissociation . We ascertained that a similar concept could be applied to hexose disaccharide lithium adducts.…”

Section: Resultsmentioning

confidence: 96%

“…A LODES for CID tandem MS was developed based on the understanding of the dissociation mechanisms of carbohydrate sodium adducts . This sequence can be used for generating the chosen mono‐ and disaccharides for subsequent structural determination.…”

Section: Resultsmentioning

confidence: 99%

“…The third one is the capability to dissociate selective chemical bonds and generate the chosen mono‐ or disaccharide for subsequent structural determination. We have developed a procedure, namely, logically derived sequence (LODES) for tandem MS, to generate the desired mono‐ or disaccharide by CID of oligosaccharide sodium adducts . We extended the method of LODES to oligosaccharide lithium adducts in this study.…”

Section: Introductionmentioning

confidence: 99%

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Automatic Full Glycan Structural Determination through Logically Derived Sequence Tandem Mass Spectrometry

et al. 2019

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Glycans have diverse functions and play vital roles in many biological systems, such as influenza, vaccines, and cancer biomarkers. However, full structural identification of glycans remains challenging. The glycan structure was conventionally determined by chemical methods or NMR spectroscopy, which require a large amount of sample and are not readily applicable for glycans extracted from biological samples. Although it has high sensitivity and is widely used for structural determination of molecules, current mass spectrometry can only reveal parts of the glycan structure. Herein, the full structures of glycans, including diastereomers, the anomericity of each monosaccharide, and the linkage position of each glycosidic bond, which can be determined by using tandem mass spectrometry guided by a logically derived sequence (LODES), are shown. This new method provides de novo oligosaccharide structural identification with high sensitivity and has been applied to automatic in situ structural determination of oligosaccharides eluted by means of HPLC. It is shown that the structure of a given trisaccharide from a trisaccharide mixture and bovine milk were determined from nearly 3000 isomers by using 6–7 logically selected collision‐induced dissociation spectra. The entire procedure for mass spectrometry measurement guided by LODES can be programmed in a computer for automatic full glycan structure identification.

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Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Automatic Full Glycan Structural Determination through Logically Derived Sequence Tandem Mass Spectrometry

et al. 2019

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“…39,40 In the present study, the CID spectrum of each disaccharide anomer was measured immediately after the separation of anomers by HPLC. Our previous study 44,45 on hexose disaccharide sodium adducts demonstrated that both the anomeric configurations of the glycosidic bond and the sugar at the reducing end can be determined using the relative intensities of glycosidic bond cleavage, dehydration, and cross-ring dissociation. We ascertained that a similar concept can be applied to hexose disaccharide lithium adducts.…”

Section: Identifications Of Linkagesmentioning

confidence: 99%

“…Reducing end is located at the monosaccharide unit 1. The colors used in this figure are simply to distinguish different types of trisaccharides, they are not related to the color codes used in the symbol nomenclature of Consortium for Functional Glycomics (CFG).Logically derived sequences (LODES) for MSn logically derived sequence (LODES) for CID tandem mass spectrometry was developed based on the understanding of the dissociation mechanisms of carbohydrate sodium adducts44,45…”

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confidence: 99%

Automatically Full Glycan Structural Determination with Logically Derived Sequence Tandem Mass Spectrometry

Tsai¹,

Liew²,

Hsu³

et al. 2019

Preprint

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Here we show the full structures of glycans, including diastereomers and anomericity of each monosaccharide and linkage position of each glycosidic bond, can be determined using tandem mass spectrometry guided by a logically derived sequence (LODES). This new method provides de novo oligosaccharide structural identifications with high sensitivity and was applied to automatically in situ structural determination of the oligosaccharides eluted by high performance liquid chromatography. We showed that the structure of a given trisaccharide from trisaccharide mixture and bovine milk were determined from near three thousand isomers by using six to seven logically selected CID spectra. The entire procedure of mass spectrum measurement guided by LODES can be programmed in computer for automatically full glycan structural identification, a goal that remains a great challenge in glycan analysis.

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Differentiation of aldohexoses and ketohexoses through collision‐induced dissociation

Tsai

2021

J Chinese Chemical Soc

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Mass spectrometry has high sensitivity and is widely used for carbohydrate structural determination. However, conventional mass spectrometry is not able to identify anomericity and stereoisomer. In this work, we demonstrate that aldohexose and ketohexose can be distinguished through the collision‐induced dissociation of sodium adducts in an ion trap mass spectrometer. The criterion for the differentiation is the intensity ratio of fragment ion m/z 143 to fragment ion m/z 113. Aldohexoses have an intensity ratio larger than 1.8 and ketohexoses have an intensity ratio less than 0.7. These ratios can be explained using a cross‐ring dissociation mechanism. Although the dissociation mechanism of lithium adducts is similar to that of sodium adducts, differentiation using lithium adducts is not as good as that of sodium adducts because of the large lithiation energies. In addition, a dehydration propensity rule to differentiate anomeric configuration is extended from glucose, galactose, and mannose to allose, altrose, gulose, talose, fructose, and tagatose in this work. Application of this method for the identification of aldohexoses and ketohexoses produced from the collision‐induced dissociation of oligosaccharides in tandem mass spectrometer is demonstrated.

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Simple Approach for De Novo Structural Identification of Mannose Trisaccharides

Cited by 42 publications

References 32 publications

Automatic Full Glycan Structural Determination through Logically Derived Sequence Tandem Mass Spectrometry

Automatic Full Glycan Structural Determination through Logically Derived Sequence Tandem Mass Spectrometry

Automatically Full Glycan Structural Determination with Logically Derived Sequence Tandem Mass Spectrometry

Differentiation of aldohexoses and ketohexoses through collision‐induced dissociation

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