ArticleJournal of the American Society for Mass Spectrometry2012
Tandem mass spectrometry of heparan sulfate negative ions: sulfate loss patterns and chemical modification methods for improvement of product ion profiles.
Article in Journal of the American Society for Mass Spectrometry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 44 citations in OpenAlex.
- Mechanistic study on the sulfate migration in glycosaminoglycans during MS fragmentation.Communications chemistry · 2026Article
- Untangling Heparan Sulfate 3-Analytical chemistry · 2025Article
- Immunoglobulin A carries sulfated andFrontiers in molecular biosciences · 2025Article
- A Concise Review of Extraction and Characterization of Chondroitin Sulphate from Fish and Fish Wastes for Pharmacological Application.Current issues in molecular biology · 2022Review
- The Key Role of Metal Adducts in the Differentiation of Phosphopeptide from Sulfopeptide Sequences by High-Resolution Mass Spectrometry.Analytical chemistry · 2022Article
- Mass Spectrometry-Based Techniques to Elucidate the Sugar Code.Chemical reviews · 2022Review
- Progress and challenges in the synthesis of sequence controlled polysaccharides.Beilstein journal of organic chemistry · 2021Review
- Peracylation Coupled with Tandem Mass Spectrometry for Structural Sequencing of Sulfated Glycosaminoglycan Mixtures without Depolymerization.Journal of the American Society for Mass Spectrometry · 2020Article
- Heparanase as an Additional Tool for Detecting Structural Peculiarities of Heparin Oligosaccharides.Molecules (Basel, Switzerland) · 2019Article
- Article
- Sequencing Heparan Sulfate Using HILIC LC-NETD-MS/MS.Analytical chemistry · 2019Article
- Structural Characterization of Glycosaminoglycan Carbohydrates Using Ultraviolet Photodissociation.Analytical chemistry · 2019Article
- Free Radical Initiated Peptide Sequencing for Direct Site Localization of Sulfation and Phosphorylation with Negative Ion Mode Mass Spectrometry.Analytical chemistry · 2018Article
- Negative Electron Transfer Dissociation Sequencing of 3-O-Sulfation-Containing Heparan Sulfate Oligosaccharides.Journal of the American Society for Mass Spectrometry · 2018Article
- Assignment Of Hexuronic Acid Stereochemistry In Synthetic Heparan Sulfate Tetrasaccharides With 2-International journal of mass spectrometry · 2015Article
- Preparation and characterization of heparin hexasaccharide library with N-unsubstituted glucosamine residues.Glycoconjugate journal · 2015Article
- A computational framework for heparan sulfate sequencing using high-resolution tandem mass spectra.Molecular & cellular proteomics : MCP · 2014Article
- De novo sequencing of heparan sulfate oligosaccharides by electron-activated dissociation.Analytical chemistry · 2013Article
- Mass spectral profiling of glycosaminoglycans from histological tissue surfaces.Analytical chemistry · 2013Article
- LC-MS and LC-MS/MS studies of incorporation of 34SO3 into glycosaminoglycan chains by sulfotransferases.Glycobiology · 2013Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Heparan sulfate (HS) is a polysaccharide modified with sulfation, acetylation, and epimerization that enable its binding with protein ligands and regulation of important biological processes. Tandem mass spectrometry has been employed to sequence linear biomolecules e.g., proteins and peptides. However, its application in structural characterization of HS is limited due to the neutral loss of sulfate (SO(3)) during collisional induced dissociation (CID). In this report, we studied the dissociation patterns of HS disaccharides and demonstrate that the N-sulfate (N-S) bond is especially facile during CID. We identified factors that influence the propensities of such losses from precursor ions and proposed a Free Proton Index (FPI) to help select ions that are able to produce meaningful backbone dissociations. We then investigated the thermodynamics and kinetics of SO(3) loss from sulfates that are protonated, deprotonated, and metal-adducted using density functional theory computations. The calculations showed that sulfate loss from a protonated site was much more facile than that from a deprotonated or metal-adducted site. Further, the loss of SO(3) from N-sulfate was energetically favored by 3-8 kcal/mol in transition states relative to O-sulfates, making it more prone to this process by a substantial factor. In order to reduce the FPI, representing the number of labile sulfates in HS native chains and oligosaccharides, we developed a series of chemical modifications to selectively replace the N-sulfates of the glucosamine with deuterated acetyl group. These modifications effectively reduced the sulfate density on the HS oligosaccharides and generated considerably more backbone dissociation using on-line LC/tandem MS.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.