Mapping of low molecular weight heparins using reversed phase ion pair liquid chromatography–mass spectrometry

Li, Daoyuan; Chi, Lequan; Jin, Lan; Xu, Xiaohui; Du, Xueli; Sheng-li, JI

doi:10.1016/j.carbpol.2013.08.074

Cited by 29 publications

(15 citation statements)

References 23 publications

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“…Also a fraction (~16%) of the LMW heparin chain reducing ends (REs) are1,6-anhydro hexosamines. More than 120 structural compositions have been reported enoxaparin oligosaccharide chains [4–5]. …”

Section: Resultsmentioning

confidence: 99%

“…LMW heparins, including innovator drugs and more recently generic versions, have undergone a great deal of regulatory scrutiny because of their polycomponent nature and their high level of structural complexity [2]. Studies of new approaches to determine the structure of LMW heparins have included bottom-up [3], top-down [4] and combined liquid chromatography (LC)-mass spectrometry (MS) analysis [5–6]. Despite these major advances, the rapid and accurate glycomic analysis of glycosaminoglycans by LC-MS has been plagued by the absence of suitable bioinformatics software.…”

Section: Introductionmentioning

confidence: 99%

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GlycCompSoft: Software for Automated Comparison of Low Molecular Weight Heparins Using Top-Down LC/MS Data

Wang

Liu

et al. 2016

PLoS ONE

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Low molecular weight heparins are complex polycomponent drugs that have recently become amenable to top-down analysis using liquid chromatography-mass spectrometry. Even using open source deconvolution software, DeconTools, and automatic structural assignment software, GlycReSoft, the comparison of two or more low molecular weight heparins is extremely time-consuming, taking about a week for an expert analyst and provides no guarantee of accuracy. Efficient data processing tools are required to improve analysis. This study uses the programming language of Microsoft Excel™ Visual Basic for Applications to extend its standard functionality for macro functions and specific mathematical modules for mass spectrometric data processing. The program developed enables the comparison of top-down analytical glycomics data on two or more low molecular weight heparins. The current study describes a new program, GlycCompSoft, which has a low error rate with good time efficiency in the automatic processing of large data sets. The experimental results based on three lots of Lovenox®, Clexane® and three generic enoxaparin samples show that the run time of GlycCompSoft decreases from 11 to 2 seconds when the data processed decreases from 18000 to 1500 rows.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

GlycCompSoft: Software for Automated Comparison of Low Molecular Weight Heparins Using Top-Down LC/MS Data

Wang

Liu

et al. 2016

PLoS ONE

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“…In particular, hyphenated MS methodologies, such as liquid chromatography (LC)-MS[4, 8–13] and more recently capillary electrophoresis (CE)-MS, are taking a leading role in these analyses[14–18]. These methods can provide enhanced resolution for the analysis of complex mixtures of heparin polysaccharide and oligosaccharide chains without loss of detection sensitivity.…”

Section: Introductionmentioning

confidence: 99%

“…These methods can provide enhanced resolution for the analysis of complex mixtures of heparin polysaccharide and oligosaccharide chains without loss of detection sensitivity. There are three types of routinely performed heparin and LMW heparin structural analysis that utilize hyphenated MS methodologies, disaccharide compositional analysis [4, 10, 11], bottom-up analysis [9, 12], and top-down analysis [8, 13]. In the case of disaccharide bottom-up analysis and compositional analysis, heparin sample is first treated with one or more heparin lyases [4, 9–12] to afford either oligosaccharides or disaccharides for subsequent LC or CE separation and MS analysis.…”

Section: Introductionmentioning

confidence: 99%

“…In the case of disaccharide bottom-up analysis and compositional analysis, heparin sample is first treated with one or more heparin lyases [4, 9–12] to afford either oligosaccharides or disaccharides for subsequent LC or CE separation and MS analysis. Top-down analysis examines the whole intact GAG chain and has been limited to either small GAG chains, such as bikunin [19], or LMW heparins[8, 13]. Electrophoresis, while offering extremely high-resolution separations is particularly complicated for on-line coupling to MS. Sheathless CE-MS interfaces points to a potentially promising direction, transferring this post-electrophoresis pre-electrospray reaction directly to sheathless CE-MS system.…”

Section: Introductionmentioning

confidence: 99%

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Analysis of heparin oligosaccharides by capillary electrophoresis–negative-ion electrospray ionization mass spectrometry

et al. 2016

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Most hyphenated analytical approaches that rely on liquid chromatography-MS require relatively long separation times, produce incomplete resolution of oligosaccharide mixtures, use eluents that are incompatible with electrospray ionization, or require oligosaccharide derivatization. Here we demonstrate the analysis of heparin oligosaccharides, including disaccharides, ultra low molecular weight heparin, and a low molecular weight heparin, using a novel electrokinetic pump-based CE-MS coupling eletrospray ion source. Reverse polarity CE separation and negative mode electrospray ionization were optimized using a volatile methanolic ammonium acetate electrolyte and sheath fluid. The on-line CE hyphenated negative-ion electrospray ionization MS on an LTQ Orbitrap mass spectrometer was useful in disaccharide compositional analysis, bottom-up and top-down analysis of low molecular weight heparin. The application of this CE-MS method to ultra low molecular heparin suggest that a charge state distribution and the low level of sulfate group loss that is achieved make this method useful on-line tandem MS analysis of heparins.

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Development of hydrophilic interaction chromatography with quadruple time‐of‐flight mass spectrometry for heparin and low molecular weight heparin disaccharide analysis

Ouyang

Sun

et al. 2015

Rapid Comm Mass Spectrometry

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Mapping of low molecular weight heparins using reversed phase ion pair liquid chromatography–mass spectrometry

Cited by 29 publications

References 23 publications

GlycCompSoft: Software for Automated Comparison of Low Molecular Weight Heparins Using Top-Down LC/MS Data

GlycCompSoft: Software for Automated Comparison of Low Molecular Weight Heparins Using Top-Down LC/MS Data

Analysis of heparin oligosaccharides by capillary electrophoresis–negative-ion electrospray ionization mass spectrometry

Development of hydrophilic interaction chromatography with quadruple time‐of‐flight mass spectrometry for heparin and low molecular weight heparin disaccharide analysis

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