Mass spectrometry for the characterization of unsulfated chondroitin oligosaccharides from 2-mers to 16-mers. Comparison with hyaluronic acid oligomers.
Identifieur interne : 001F77 ( PubMed/Checkpoint ); précédent : 001F76; suivant : 001F78Mass spectrometry for the characterization of unsulfated chondroitin oligosaccharides from 2-mers to 16-mers. Comparison with hyaluronic acid oligomers.
Auteurs : Nicola Volpi [Italie] ; Zhenqing Zhang ; Robert J. LinhardtSource :
- Rapid communications in mass spectrometry : RCM [ 0951-4198 ] ; 2008.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Chondroitin, Hyaluronic Acid, Oligosaccharides.
- chemistry : Escherichia coli.
- methods : Chromatography, Liquid, Mass Spectrometry.
Abstract
This study reports for the first time the complete liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS) and tandem mass spectrometry (MS/MS) analyses performed in negative ion mode of saturated unsulfated chondroitin oligosaccharides up to 16-mers and comparison with hyaluronic acid (HA) oligomers differing only in the nature of the hexosamine residue. MS/MS of the chondroitin disaccharide on the singly charged precursor at m/z 396.1 afforded a glycosidic cleavage C1 product ion at m/z 192.9. In the tetrasaccharide, C2 (m/z 396.0) and C3 (m/z 572.0) product anions were generated by glycosidic cleavage. A C5 [M-2H]2- product ion at m/z 475.1 was generated by the glycosidic cleavage of the hexasaccharide, and a C7 ion (m/z 664.6, charge state of -2) was produced from the octasaccharide. The same fragmentation pattern of deprotonated oligomers was observed for the largest oligosaccharides, from 10- to 16-mers. There has been no previous report of MS/MS spectra for unsulfated chondroitin oligomers of these sizes. Unsulfated saturated chondroitin oligosaccharides with x-mer units and larger than a tetrasaccharide dissociate to almost exclusively form CX-1-type ions. Saturated HA oligomers also afforded the same fragmentation pattern as deprotonated oligomers by ESI-MS and MS/MS analyses. Thus, under the experimental conditions used in the current study, we were unable to distinguish between unsulfated chondroitin and HA.
DOI: 10.1002/rcm.3760
PubMed: 18853395
Affiliations:
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<keywords scheme="KwdFr" xml:lang="fr"><term>Acide hyaluronique ()</term>
<term>Chondroïtine ()</term>
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<term>Chondroïtine</term>
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<front><div type="abstract" xml:lang="en">This study reports for the first time the complete liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS) and tandem mass spectrometry (MS/MS) analyses performed in negative ion mode of saturated unsulfated chondroitin oligosaccharides up to 16-mers and comparison with hyaluronic acid (HA) oligomers differing only in the nature of the hexosamine residue. MS/MS of the chondroitin disaccharide on the singly charged precursor at m/z 396.1 afforded a glycosidic cleavage C1 product ion at m/z 192.9. In the tetrasaccharide, C2 (m/z 396.0) and C3 (m/z 572.0) product anions were generated by glycosidic cleavage. A C5 [M-2H]2- product ion at m/z 475.1 was generated by the glycosidic cleavage of the hexasaccharide, and a C7 ion (m/z 664.6, charge state of -2) was produced from the octasaccharide. The same fragmentation pattern of deprotonated oligomers was observed for the largest oligosaccharides, from 10- to 16-mers. There has been no previous report of MS/MS spectra for unsulfated chondroitin oligomers of these sizes. Unsulfated saturated chondroitin oligosaccharides with x-mer units and larger than a tetrasaccharide dissociate to almost exclusively form CX-1-type ions. Saturated HA oligomers also afforded the same fragmentation pattern as deprotonated oligomers by ESI-MS and MS/MS analyses. Thus, under the experimental conditions used in the current study, we were unable to distinguish between unsulfated chondroitin and HA.</div>
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<Abstract><AbstractText>This study reports for the first time the complete liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS) and tandem mass spectrometry (MS/MS) analyses performed in negative ion mode of saturated unsulfated chondroitin oligosaccharides up to 16-mers and comparison with hyaluronic acid (HA) oligomers differing only in the nature of the hexosamine residue. MS/MS of the chondroitin disaccharide on the singly charged precursor at m/z 396.1 afforded a glycosidic cleavage C1 product ion at m/z 192.9. In the tetrasaccharide, C2 (m/z 396.0) and C3 (m/z 572.0) product anions were generated by glycosidic cleavage. A C5 [M-2H]2- product ion at m/z 475.1 was generated by the glycosidic cleavage of the hexasaccharide, and a C7 ion (m/z 664.6, charge state of -2) was produced from the octasaccharide. The same fragmentation pattern of deprotonated oligomers was observed for the largest oligosaccharides, from 10- to 16-mers. There has been no previous report of MS/MS spectra for unsulfated chondroitin oligomers of these sizes. Unsulfated saturated chondroitin oligosaccharides with x-mer units and larger than a tetrasaccharide dissociate to almost exclusively form CX-1-type ions. Saturated HA oligomers also afforded the same fragmentation pattern as deprotonated oligomers by ESI-MS and MS/MS analyses. Thus, under the experimental conditions used in the current study, we were unable to distinguish between unsulfated chondroitin and HA.</AbstractText>
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<ReferenceList><Reference><Citation>J Biol Chem. 2003 Jan 31;278(5):3063-71</Citation>
<ArticleIdList><ArticleId IdType="pubmed">12446672</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Biol Chem. 2002 Oct 11;277(41):38189-96</Citation>
<ArticleIdList><ArticleId IdType="pubmed">12163485</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Glycobiology. 2003 Sep;13(9):635-40</Citation>
<ArticleIdList><ArticleId IdType="pubmed">12702669</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Chromatogr A. 2003 Oct 3;1014(1-2):215-23</Citation>
<ArticleIdList><ArticleId IdType="pubmed">14558627</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Biol Chem. 2003 Dec 5;278(49):49261-70</Citation>
<ArticleIdList><ArticleId IdType="pubmed">12972412</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Biol Chem. 2004 Jan 23;279(4):2608-15</Citation>
<ArticleIdList><ArticleId IdType="pubmed">14610083</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Electrophoresis. 2004 Feb;25(4-5):692-6</Citation>
<ArticleIdList><ArticleId IdType="pubmed">14981698</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Eur J Biochem. 1988 Oct 15;177(1):117-24</Citation>
<ArticleIdList><ArticleId IdType="pubmed">2460347</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Glycoconj J. 1994 Apr;11(2):123-32</Citation>
<ArticleIdList><ArticleId IdType="pubmed">7804002</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Biol Chem. 2005 Feb 18;280(7):5435-48</Citation>
<ArticleIdList><ArticleId IdType="pubmed">15590670</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Am Soc Mass Spectrom. 2007 May;18(5):952-60</Citation>
<ArticleIdList><ArticleId IdType="pubmed">17383193</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Anal Chem. 2007 Aug 15;79(16):6390-7</Citation>
<ArticleIdList><ArticleId IdType="pubmed">17608452</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Rapid Commun Mass Spectrom. 2007;21(21):3459-66</Citation>
<ArticleIdList><ArticleId IdType="pubmed">17922485</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Am Soc Mass Spectrom. 2008 Jan;19(1):82-90</Citation>
<ArticleIdList><ArticleId IdType="pubmed">18061476</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Am Chem Soc. 2002 Jul 24;124(29):8707-18</Citation>
<ArticleIdList><ArticleId IdType="pubmed">12121115</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Electrophoresis. 2003 Mar;24(6):1063-8</Citation>
<ArticleIdList><ArticleId IdType="pubmed">12658696</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
</PubmedData>
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