Applications of Mass Spectrometry to Structural Analysis of Marine Oligosaccharides

Lang, Yinzhi; Zhao, Xia; Liu, Huan; Yu, Guangli

doi:10.3390/md12074005

Cited by 33 publications

(20 citation statements)

References 76 publications

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“…Qualitative techniques are essential. Electrospray ionization mass spectrometry and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) are frequently used for rapidly and reliably identifying COS with various DPs and DDs and for elucidating detailed structural information, such as molecular weight and average DP [7,8,9,10]. To separate and analyze a single COS, high-performance liquid chromatography (HPLC) coupled with various detectors was frequently used.…”

Section: Introductionmentioning

confidence: 99%

Validated HPAEC-PAD Method for the Determination of Fully Deacetylated Chitooligosaccharides

Cao

Wu²,

et al. 2016

IJMS

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An efficient and sensitive analytical method based on high-performance anion exchange chromatography with pulsed amperometric detection (HPAEC-PAD) was established for the simultaneous separation and determination of glucosamine (GlcN)1 and chitooligosaccharides (COS) ranging from (GlcN)2 to (GlcN)6 without prior derivatization. Detection limits were 0.003 to 0.016 mg/L (corresponding to 0.4–0.6 pmol), and the linear range was 0.2 to 10 mg/L. The optimized analysis was carried out on a CarboPac-PA100 analytical column (4 × 250 mm) using isocratic elution with 0.2 M aqueous sodium hydroxide-water mixture (10:90, v/v) as the mobile phase at a 0.4 mL/min flow rate. Regression equations revealed a good linear relationship (R2 = 0.9979–0.9995, n = 7) within the test ranges. Quality parameters, including precision and accuracy, were fully validated and found to be satisfactory. The fully validated HPAEC-PAD method was readily applied for the quantification of (GlcN)1–6 in a commercial COS technical concentrate. The established method was also used to monitor the acid hydrolysis of a COS technical concentrate to ensure optimization of reaction conditions and minimization of (GlcN)1 degradation.

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Section: Introductionmentioning

confidence: 99%

Validated HPAEC-PAD Method for the Determination of Fully Deacetylated Chitooligosaccharides

Cao

Wu²,

et al. 2016

IJMS

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“…Incubations were performed at 37°C for 22 h. Samples were analyzed for heptasaccharide fragmentation by MALDI-TOF MS in a 2,5-dihydroxybenzoic acid matrix at the Albert Einstein College of Medicine Proteomics Facility (Bronx, NY). Fragmentation analysis for heptasaccharide was done as described previously for polysaccharides (68,69). All glycosidic cleavages (Z-, Y-, B-, and C-type) as well as cross-ring cleavages (X-and A-type) were examined.…”

Section: − I − − T Qs P − S L S − S − G− − − T I − C − − S − S − − − mentioning

confidence: 99%

A Monoclonal Antibody to Cryptococcus neoformans Glucuronoxylomannan Manifests Hydrolytic Activity for Both Peptides and Polysaccharides

Bowen

Wear

Cordero

et al. 2017

Journal of Biological Chemistry

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Edited by Luke O'NeillStudies in the 1980s first showed that some natural antibodies were "catalytic" and able to hydrolyze peptide or phosphodiester bonds in antigens. Many naturally occurring catalytic antibodies have since been isolated from human sera and associated with positive and negative outcomes in autoimmune disease and infection. The function and prevalence of these antibodies, however, remain unclear. A previous study suggested that the 18B7 monoclonal antibody against glucuronoxylomannan (GXM), the major component of the Cryptococcus neoformans polysaccharide capsule, hydrolyzed a peptide antigen mimetic. Using mass spectrometry and Förster resonance energy transfer techniques, we confirm and characterize the hydrolytic activity of 18B7 against peptide mimetics and show that 18B7 is able to hydrolyze an oligosaccharide substrate, providing the first example of a naturally occurring catalytic antibody for polysaccharides. Additionally, we show that the catalytic 18B7 antibody increases release of capsular polysaccharide from fungal cells. A serine protease inhibitor blocked peptide and oligosaccharide hydrolysis by 18B7, and a putative serine protease-like active site was identified in the light chain variable region of the antibody. An algorithm was developed to detect similar sites present in unique antibody structures in the Protein Data Bank. The putative site was found in 14 of 63 (22.2%) catalytic antibody structures and 119 of 1602 (7.4%) antibodies with no annotation of catalytic activity. The ability of many antibodies to cleave antigen, albeit slowly, supports the notion that this activity is an important immunoglobulin function in host defense. The discovery of GXM hydrolytic activity suggests new therapeutic possibilities for polysaccharide-binding antibodies.A central tenet in immunology is that immunoglobulin (Ig) variable (V) 2 regions bind antigen (Ag) and that the molecule's constant regions activate complement components or cellular receptors, triggering downstream immune pathways such as phagocytosis, granule release, cell-mediated cytotoxicity, and complement-mediated cytotoxicity. Research has also shown that antibodies possess important direct effects on Ag, such as neutralization of toxins or virions, bacterial agglutination, and precipitation of soluble Ag. Although it has long been accepted that each of these Ig functions are mediated by the binding of an antibody paratope to an Ag epitope, research in 1975 first showed that antibodies could be generated that not only bound Ag but also catalyzed a chemical reaction in the Ag substrate (1). Over the next 2 decades, many catalytic antibodies were generated against haptenic transition state analogues to catalyze a wide array of chemical reactions, a strategy first proposed by enzymologist W. Jencks in 1969 (2). This strategy has since been used to generate antibody catalysts for many distinct chemical reactions, albeit with reaction rates usually much slower than natural enzymes. The first indication that some naturally occurri...

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“…The study of structural details (such as ramification, substitution etc.) of well-defined molecular size oligosaccharides has gained attention by NMR chemical shifts assignments and mass spectrometry in combination (Duus et al, 2000;Lang et al, 2014;Préchoux and Helbert, 2014). Few biological applications of algae-derived oligosaccharides and their recent relevant advancements are illustrated in this review with keen foresight on future perspectives.…”

Section: Algae-derived Marine Oligosaccharidesmentioning

confidence: 99%

“…More research to understand the structural properties of these oligosaccharides are essential to utilize them efficiently. Mass spectrometry (MS) based studies provide the structural characterization of these oligosaccharides in more precise, reproducible and reliable manner (Stahl et al, 2002;Zaia, 2004;Mischnick, 2012;Lang et al, 2014). Thus, the differential liability of certain residues or chemical groups for the elucidation of the depolymerization mechanisms has to be further investigated with a multi-disciplinary approach for the fine structural analysis of algae-derived marine oligosaccharides.…”

Section: Introductionmentioning

confidence: 99%

Algae-Derived Marine Oligosaccharides and Their Biological Applications

2016

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The biological relevance of algae-derived marine oligosaccharides has potential significance in numerous applications of industrial biotechnology. Marine oligosaccharides are produced in algae naturally and/or by hydrolysis of derived polysaccharides. The potential of marine oligosaccharides is still unexplored, and these molecules, including their derivatives, are a versatile source of chemical diversity. In-depth knowledge on such molecules will provide novel insights, thus depicting their role in discovering mechanisms and the molecular functions within specific biological applications.

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Applications of Mass Spectrometry to Structural Analysis of Marine Oligosaccharides

Cited by 33 publications

References 76 publications

Validated HPAEC-PAD Method for the Determination of Fully Deacetylated Chitooligosaccharides

Validated HPAEC-PAD Method for the Determination of Fully Deacetylated Chitooligosaccharides

A Monoclonal Antibody to Cryptococcus neoformans Glucuronoxylomannan Manifests Hydrolytic Activity for Both Peptides and Polysaccharides

Algae-Derived Marine Oligosaccharides and Their Biological Applications

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