This review is the tenth update of the original article published in 1999 on the application of matrix-assisted laser desorption/ionization (MALDI) mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2020. Also included are papers that describe methods appropriate to analysis by MALDI, such as sample preparation techniques, even though the ionization method is not MALDI. The review is basically divided into three sections: (1) general aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, fragmentation, quantification and the use of arrays. (2) Applications to various structural types such as oligo- and polysaccharides, glycoproteins, glycolipids, glycosides and biopharmaceuticals, and (3) other areas such as medicine, industrial processes and glycan synthesis where MALDI is extensively used. Much of the material relating to applications is presented in tabular form. The reported work shows increasing use of incorporation of new techniques such as ion mobility and the enormous impact that MALDI imaging is having. MALDI, although invented nearly 40 years ago is still an ideal technique for carbohydrate analysis and advancements in the technique and range of applications show little sign of diminishing. This article is protected by copyright. All rights reserved.

Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: An update for 2019-2020.

Protein glycosylation plays a critical and non-negligible role in many biological processes, and some glycosylated proteins are important biomarkers. However, the identification and analysis of these biomarkers usually require the aid of effective enrichment strategies and high-quality mass spectrometric detection techniques. Among these, mesoporous nanomaterials with large specific surface areas and abundant tunable pore channels stand out, and their use for the development of novel glycopeptide enrichment and separation strategies has attractive potential. In this review, we discuss recent advances in mesoporous nanomaterials in glycoproteomics over the past five years, including their different compositions and mechanisms of the synthesis process, with a particular focus on their application in complex samples including body fluids, cells, tissues, and food. Additionally, bottlenecks and future directions in the development of mesoporous materials for glycopeptide separation are discussed, such as the capture of serum-derived and cell-derived exosomes and the exploration of related areas. 

Mesoporous materials for glycopeptide separation

We report the electrochemical behavior of free-standing functionalized graphene sheet electrode in a potential window corresponding to that of high-voltage cathode of lithium-ion batteries. Electrochemical exfoliation of graphite yielded graphene oxide sheets that were subsequently heat-treated at 300 °C in inert gas atmosphere. Chemical functionalization of resulting graphene sheets with C6H4CF3, C6H4COOH, and C6H4N(C2H5)2 groups was performed using diazonium chemistry. As-prepared graphene oxide and heat-treated unmodified and modified graphene electrodes were characterized by elemental analysis, 4-point probe measurements, Raman spectroscopy, X-ray photoelectron spectroscopy, galvanostatic cycling, and cyclic voltammetry. A smaller voltammetric charge was obtained for electrodes made with graphene sheets functionalized with aryl groups compared to that of unmodified graphene. In addition, the irreversible charge (difference between oxidation and reduction charge) for C6H4CF3-functionalized graphene electrode is much smaller than that of unmodified electrode. These observations suggest that substituted aryl groups grafted on graphene sheets surface can mitigate side reactions at the electrode/electrolyte interface, and the resulting materials could be useful as conductive additive of a high voltage composite electrode.

https://link.springer.com/content/pdf/10.1007/s10008-020-04843-4.pdf

Synthesis and characterization of aryl substituted functionalized graphene sheets and their electrochemical behavior

The comprehensive characterization of N-glycans is of significant importance for the discovery of potential biomarkers and the diagnosis and therapy of diseases. Herein, we designed and fabricated a porous graphitized carbon biomaterial (CS-900-1C) using cheap and available chitosan as the carbon source via a facile pyrolysis process and a post-oxidation strategy for the effective capture of N-glycans. Thanks to its large surface area (2846 m2 g-1), high graphitization degree, suitable oxidation degree and unique porous structure, the CS-900-1C biomaterial exhibits an ultralow detection limit (1 ng μL-1), an excellent size-exclusion effect (OVA digest : BSA protein : OVA protein, 1 : 1000 : 1000, w/w/w) and satisfactory reusability (at least 8 cycles) in the capture of standard N-glycans. Moreover, CS-900-1C has successfully been applied in profiling the difference of N-glycans during diabetes progression (obesity, impaired glucose tolerance, diabetes patients and healthy control) where we discovered that the expression levels of five N-glycans show a gradually increasing trend as diabetes progresses. Remarkably, the five specific N-glycans could be considered as biomarkers to accurately diagnose the progression of diabetes. Our work not only developed a novel porous graphitized carbon biomaterial for the large-scale characterization of N-glycans but also provided new guidance for the precise therapy of diabetes.

Facile preparation of a novel chitosan-derived porous graphitized carbon biomaterial for highly efficient capture of N-glycans.

Due to the highly heterogeneous nature of hepatocellular carcinoma (HCC), the accurate diagnosis of HCC during the early phase of development is still a challenging task. Therefore, the further development of novel diagnostic methods by discovering new biomarkers is required to improve the rate of HCC diagnosis in the early phase. In this work, an oxygen-modified three-dimensional interconnected porous carbon probe is designed and fabricated to profile the differences of N-glycans in human serum from health controls (H) and patients with hepatic dysfunction (HD) and HCC for the discovery of new biomarkers with HCC development. Excitingly, we discovered that the expression levels of 12 serum N-glycans were gradually increased from H to patients with HD and eventually to patients with HCC. Moreover, two machine learning models established based on these 12 serum N-glycans reached a satisfactory accuracy for predicting HCC development where the receiver operating characteristic curve arrived above 0.95 for distinguishing healthy controls and patients with liver diseases (HD or HCC) and the ROC curve arrived at 0.85 for distinguishing HD and HCC. Our work not only developed a new method for the large-scale characterization of serum N-glycans but also provided valuable guidance for accurate and highly sensitive diagnosis of early liver cancer development in a non-invasive manner.

Novel Three-Dimensional Hierarchical Porous Carbon Probe for the Discovery of N-Glycan Biomarkers and Early Hepatocellular Carcinoma Detection.

In this work, an enrichment approach for the profiling of N-linked glycans was developed by utilizing a highly porous 3D graphene composite fabricated from graphene oxide nanosheets and a phenol-formaldehyde polymer via graphitization and KOH activation. In tailoring the large surface area (ca. 2213 m2 g−1) and 3D-layered mesoporous structure, the 3D graphene composite demonstrated not only high efficiency in glycan enrichment but also the size-exclusion effect against residual protein interference. For a standard protein ovalbumin digest, 26 N-linked glycans were identified with good repeatability, and the detection limit was as low as 0.25 ng μL−1 with the identification of 13 N-linked glycans (S/N > 10). When the mass ratio of the ovalbumin digest to the interfering proteins, i.e., bovine serum albumin and ovalbumin was 1 : 2000 : 2000, 18 N-linked glycans could still be detected with sufficient signal intensities. From a 60 nL minute complex human serum sample, up to 53 N-linked glycans with S/N > 10 were identified after the 3D graphene enrichment, while only 20 N-linked glycans were identified by the porous graphitized carbon material used for comparison. In addition, the application of the 3D graphene composite in profiling the up-regulated and down-regulated N-linked glycans from the real clinical serum samples of ovarian cancer patients confirmed the potential of the 3D graphene composite for analyzing minute and complicated biological samples.

The efficient profiling of serum N-linked glycans by a highly porous 3D graphene composite

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The efficient profiling of serum N-linked glycans by a highly porous 3D graphene composite