Screening enoxaparin tetrasaccharide SEC fractions for 3-O-sulfo-N-sulfoglucosamine residues using [1H,15N] HSQC NMR

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• 作者：Consuelo N. Beecher ; Matthew S. Manighalam…
• 关键词：Low molecular weight heparin ; Glycosaminoglycan ; HSQC ; Nuclear magnetic resonance ; Size ; exclusion chromatography ; Strong anion ; exchange chromatography
• 刊名：Analytical and Bioanalytical Chemistry
• 出版年：2016
• 出版时间：February 2016
• 年：2016
• 卷：408
• 期：6
• 页码：1545-1555
• 全文大小：1,584 KB
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• 作者单位：Consuelo N. Beecher (1)
  Matthew S. Manighalam (1)
  Adanma F. Nwachuku (1)
  Cynthia K. Larive (1)
  
  1. Department of Chemistry, University of California, Riverside, 501 Big Springs Rd, Riverside, California, 92521, USA
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Analytical Chemistry
  Food Science
  Inorganic Chemistry
  Physical Chemistry
  Monitoring, Environmental Analysis and Environmental Ecotoxicology
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1618-2650

文摘

Heparin and heparan sulfate (HS) are important in mediating a variety of biological processes through binding to myriad different proteins. Specific structural elements along the polysaccharide chains are essential for high affinity protein binding, such as the 3-O-sulfated N-sulfoglucosamine (GlcNS3S) residue, a relatively rare modification essential for heparin’s anticoagulant activity. The isolation of 3-O-sulfated oligosaccharides from complex mixtures is challenging because of their low abundance. Although methods such as affinity chromatography are useful in isolating oligosaccharides that bind specific proteins with high affinity, other important 3-O-sulfated oligosaccharides may easily be overlooked. Screening preparative-scale size-exclusion chromatography (SEC) fractions of heparin or HS digests using [1H,15N] HSQC NMR allows the identification of fractions containing 3-O-sulfated oligosaccharides through the unique 1H and 15N chemical shifts of the GlcNS3S residue. Those SEC fractions containing 3-O-sulfated oligosaccharides can then be isolated using strong anion-exchange (SAX)–HPLC. Compared with the results obtained by pooling the fractions comprising a given SEC peak, SAX–HPLC analysis of individual SEC fractions produces a less complicated chromatogram in which the 3-O-sulfated oligosaccharides are enriched relative to more abundant components. The utility of this approach is demonstrated for tetrasaccharide SEC fractions of the low molecular weight heparin drug enoxaparin facilitating the isolation and characterization of an unsaturated 3-O-sulfated tetrasaccharide containing a portion of the antithrombin-III binding sequence.