Glycosaminoglycan Quality Control by Monosaccharide Analysis.
1-phenyl-3-methyl-5-pyrazolone (PMP)
Chondroitin sulfate
Dermatan sulfate
Glycosaminoglycan
Heparan sulfate
Heparin
High performance liquid chromatography
Hydrolysis
Mass spectrometry
PCR instrument
Journal
Methods in molecular biology (Clifton, N.J.)
ISSN: 1940-6029
Titre abrégé: Methods Mol Biol
Pays: United States
ID NLM: 9214969
Informations de publication
Date de publication:
2022
2022
Historique:
entrez:
9
10
2021
pubmed:
10
10
2021
medline:
8
1
2022
Statut:
ppublish
Résumé
Glycosaminoglycans (GAGs) are heterogeneous biomacromolecules made by all animal cells with overlapping molecular weight and high negative charge densities, which make thorough separation of different types of GAGs and elimination of all GAG-binding proteins difficult. Even with the constant challenge of quality control, chondroitin sulfate, dermatan sulfate, heparan sulfate, and heparin glycosaminoglycans (GAGs) have been used as nutraceuticals and modern drugs for many years worldwide. Testing galactosamine in heparin has been added to the USP monograph after contaminated heparin event, but the general monosaccharide composition analysis has not been developed for GAG quality control purposes. Using a PCR-facilitated hydrolysis assay, the hydrolyzed GAG saccharides were labeled with 1-phenyl-3-methyl-5-pyrazolone (PMP) and quantified by high performance liquid chromatography (HPLC) coupled with mass spectrometry (MS). Glucosamine was found in both chondroitin sulfate and dermatan sulfate whereas galactosamine was observed in both heparan sulfate and heparin, indicating the cross contamination among different types of GAGs. Moreover, fucose was detected in chondroitin sulfate, dermatan sulfate, and heparan sulfate, and both fucose and mannose were detected in chondroitin sulfate, suggesting the co-presence of other types of glycans or novel fucosylated GAG structures. Furthermore, both the amount and structure of acid-resistant disaccharides provide distinguishable features for each type of GAGs at the same hydrolysis condition. Thus, monosaccharide analysis provides a practical and quantitative way for GAG quality control.
Identifiants
pubmed: 34626388
doi: 10.1007/978-1-0716-1398-6_24
doi:
Substances chimiques
Glycosaminoglycans
0
Monosaccharides
0
Dermatan Sulfate
24967-94-0
Fucose
28RYY2IV3F
Galactosamine
7535-00-4
Heparin
9005-49-6
Chondroitin Sulfates
9007-28-7
Heparitin Sulfate
9050-30-0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
297-306Informations de copyright
© 2022. Springer Science+Business Media, LLC, part of Springer Nature.
Références
Zhang L (2010) Glycosaminoglycan (GAG) biosynthesis and GAG-binding proteins. Prog Mol Biol Transl Sci 93:1–17
doi: 10.1016/S1877-1173(10)93001-9
Tang Y et al (2019) Biological mechanisms of glycan- and glycosaminoglycan-based nutraceuticals. Prog Mol Biol Transl Sci 163:445–469
doi: 10.1016/bs.pmbts.2019.02.012
Hao C et al (2019) Heparin: an essential drug for modern medicine. Prog Mol Biol Transl Sci 163:1–19
doi: 10.1016/bs.pmbts.2019.02.002
Dou HQ et al (2019) Heparinoids Danaparoid and Sulodexide as clinically used drugs. Prog Mol Biol Transl Sci 163:55–74
doi: 10.1016/bs.pmbts.2019.02.005
Keire DA et al (2011) Characterization of currently marketed heparin products: key tests for quality assurance. Anal Bioanal Chem 399(2):581–591
doi: 10.1007/s00216-010-4023-y
Pan J et al (2010) Oversulfated chondroitin sulfate is not the sole contaminant in heparin. Nat Biotechnol 28(3):203–207; author reply 207-11
doi: 10.1038/nbt0310-203
Pan J et al (2010) Identification of chemically sulfated/desulfated glycosaminoglycans in contaminated heparins and development of a simple assay that detects most contaminants in heparin. Glycobiol Insights 2:1–12
doi: 10.4137/GBI.S4237
Mourao PAS (2004) Use of sulfated fucans as anticoagulant and antithrombotic agents: future perspectives. Curr Pharm Des 10(9):967–981
doi: 10.2174/1381612043452730
Taylor SL et al (2019) By-products of heparin production provide a diverse source of heparin-like and Heparan sulfate glycosaminoglycans. Sci Rep 9:2679
doi: 10.1038/s41598-019-39093-6
Liu HY, Zhang ZQ, Linhardt RJ (2009) Lessons learned from the contamination of heparin. Nat Prod Rep 26(3):313–321
doi: 10.1039/b819896a
Yu Y et al (2017) Surprising absence of heparin in the intestinal mucosa of baby pigs. Glycobiology 27(1):57–63
doi: 10.1093/glycob/cww104
Ouyang Y et al (2019) Chemometric analysis of porcine, bovine and ovine heparins. J Pharm Biomed Anal 164:345–352
doi: 10.1016/j.jpba.2018.10.052
Wang QC et al (2016) Influences of acidic reaction and hydrolytic conditions on monosaccharide composition analysis of acidic, neutral and basic polysaccharides. Carbohydr Polym 143:296–300
doi: 10.1016/j.carbpol.2016.02.023
Xu GG et al (2018) Revisiting monosaccharide analysis - quantitation of a comprehensive set of monosaccharides using dynamic multiple reaction monitoring. Analyst 143(1):200–207
doi: 10.1039/C7AN01530E
Studelska DR et al (2006) Quantification of glycosaminoglycans by reversed-phase HPLC separation of fluorescent isoindole derivatives. Glycobiology 16(1):65–72
doi: 10.1093/glycob/cwj037
Conrad HE (1980) The acid lability of the glycosidic bonds of L-iduronic acid residues in glycosaminoglycans. Biochem J 191(2):355–363
doi: 10.1042/bj1910355
Zhu H et al (2014) Acidolysis-based component mapping of glycosaminoglycans by reversed-phase high-performance liquid chromatography with off-line electrospray ionization-tandem mass spectrometry: evidence and tags to distinguish different glycosaminoglycans. Anal Biochem 465:63–69
doi: 10.1016/j.ab.2014.07.021
Zhang Z et al (2012) Complete monosaccharide analysis by high-performance anion-exchange chromatography with pulsed amperometric detection. Anal Chem 84(9):4104–4110
doi: 10.1021/ac300176z
He Y et al (2018) Optimizing microwave-assisted hydrolysis conditions for monosaccharide composition analyses of different polysaccharides. Int J Biol Macromol 118(Pt A):327–332
doi: 10.1016/j.ijbiomac.2018.06.077
Zhang M et al (2020) Using a PCR instrument to hydrolyze polysaccharides for monosaccharide composition analyses. Carbohydr Polym 240:116
Kuberan B et al (2002) Analysis of heparan sulfate oligosaccharides with ion pair-reverse phase capillary high performance liquid chromatography-microelectrospray ionization time-of-flight mass spectrometry. J Am Chem Soc 124(29):8707–8718
doi: 10.1021/ja0178867
Fransson LA, Roden L, Spach ML (1968) Automated ion-exchange chromatography of uronic acids and uronic acid containing oligosaccharides. Anal Biochem 23(2):317–330
doi: 10.1016/0003-2697(68)90362-X