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Sequence analysis of the pyruvylated galactan sulfate-derived oligosaccharides by negative-ion electrospray tandem mass spectrometry.
Carbohydr Res. 2016 Oct 04; 433:80-8.CR

Abstract

Five sulfated oligosaccharide fragments, F1-F5, were prepared from a pyruvylated galactan sulfate from the green alga Codium divaricatum, by partial depolymerization using mild acid hydrolysis and purification with gel-permeation chromatography. Negative-ion electrospray tandem mass spectrometry with collision-induced dissociation (ES-CID-MS/MS) is attempted for sequence determination of the sulfated oligosaccharides. The sequence of F1 with homogeneous disaccharide composition was first characterized to be Galp-(4SO4)-(1 → 3)-Galp by detailed nuclear magnetic resonance spectroscopic analyses. The fragmentation pattern of F1 in the product ion spectra was established on the basis of negative-ion ES-CID MS/MS, which was then applied to sequence analysis of other sulfated oligosaccharides. The sequences of F2 and F3 were deduced to be Galp-(4SO4)-(1 → 3)-Galp-(1 → 3)-Galp-(1 → 3)-Galp and 3,4-O-(1-carboxyethylidene)-Galp-(6SO4)-(1 → 3)-Galp, respectively. The sequences of major fragments in F4 and F5 were also deduced. The investigation demonstrated that negative-ion ES-CID-MS/MS was an efficient method for the sequence analysis of the pyruvylated galactan sulfate-derived oligosaccharides which revealed the patterns of substitution and glycosidic linkages. The pyruvylated galactan sulfate-derived oligosaccharides were novel sulfated oligosaccharides different from other algal polysaccharide-derived oligosaccharides.

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Authors+Show Affiliations

Key Laboratory of Marine Drugs, Ministry of Education, Institute of Marine Drug and Food, Ocean University of China, Qingdao 266003, People's Republic of China; Department of Food and Biochemical Engineering, Yantai Vocational College, Yantai 264670, People's Republic of China.

Key Laboratory of Marine Drugs, Ministry of Education, Institute of Marine Drug and Food, Ocean University of China, Qingdao 266003, People's Republic of China. Electronic address: wenjunmqd@hotmail.com.

Key Laboratory of Marine Drugs, Ministry of Education, Institute of Marine Drug and Food, Ocean University of China, Qingdao 266003, People's Republic of China.

Key Laboratory of Marine Drugs, Ministry of Education, Institute of Marine Drug and Food, Ocean University of China, Qingdao 266003, People's Republic of China.

Key Laboratory of Marine Drugs, Ministry of Education, Institute of Marine Drug and Food, Ocean University of China, Qingdao 266003, People's Republic of China.

Key Laboratory of Marine Drugs, Ministry of Education, Institute of Marine Drug and Food, Ocean University of China, Qingdao 266003, People's Republic of China.

Key Laboratory of Marine Drugs, Ministry of Education, Institute of Marine Drug and Food, Ocean University of China, Qingdao 266003, People's Republic of China.

Key Laboratory of Marine Drugs, Ministry of Education, Institute of Marine Drug and Food, Ocean University of China, Qingdao 266003, People's Republic of China.

Key Laboratory of Marine Drugs, Ministry of Education, Institute of Marine Drug and Food, Ocean University of China, Qingdao 266003, People's Republic of China.

MeSH

Carbohydrate SequenceGalactansOligosaccharidesPyruvatesSpectrometry, Mass, Electrospray IonizationSulfatesTandem Mass Spectrometry

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27471831

Citation

Li, Na, et al. "Sequence Analysis of the Pyruvylated Galactan Sulfate-derived Oligosaccharides By Negative-ion Electrospray Tandem Mass Spectrometry." Carbohydrate Research, vol. 433, 2016, pp. 80-8.

Li N, Mao W, Liu X, et al. Sequence analysis of the pyruvylated galactan sulfate-derived oligosaccharides by negative-ion electrospray tandem mass spectrometry. Carbohydr Res. 2016;433:80-8.

Li, N., Mao, W., Liu, X., Wang, S., Xia, Z., Cao, S., Li, L., Zhang, Q., & Liu, S. (2016). Sequence analysis of the pyruvylated galactan sulfate-derived oligosaccharides by negative-ion electrospray tandem mass spectrometry. Carbohydrate Research, 433, 80-8. https://doi.org/10.1016/j.carres.2016.07.018

Li N, et al. Sequence Analysis of the Pyruvylated Galactan Sulfate-derived Oligosaccharides By Negative-ion Electrospray Tandem Mass Spectrometry. Carbohydr Res. 2016 Oct 4;433:80-8. PubMed PMID: 27471831.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Sequence analysis of the pyruvylated galactan sulfate-derived oligosaccharides by negative-ion electrospray tandem mass spectrometry. AU - Li,Na, AU - Mao,Wenjun, AU - Liu,Xue, AU - Wang,Shuyao, AU - Xia,Zheng, AU - Cao,Sujian, AU - Li,Lin, AU - Zhang,Qi, AU - Liu,Shan, Y1 - 2016/07/20/ PY - 2016/05/11/received PY - 2016/07/05/revised PY - 2016/07/18/accepted PY - 2016/7/30/entrez PY - 2016/7/30/pubmed PY - 2017/2/28/medline KW - 1-Phenyl-3-methyl-5-pyrazolone (PubChem CID: 90474051) KW - Acetonitrile (PubChem CID: 6342) KW - Ammonium bicarbonate (PubChem CID: 14013) KW - Barium rhodizonic acid (PubChem CID: 45048930) KW - Codium divaricatum KW - D-galactose (PubChem CID: 6036) KW - Deuterium oxide (PubChem CID: 24602) KW - ES-CID-MS/MS KW - Oligosaccharides KW - Potassium bromide (PubChem CID: 253877) KW - Pyruvylated galactan sulfate KW - Sequence KW - Sodium hydroxide (PubChem CID: 14798) KW - Sulfuric acid (PubChem CID: 1118) KW - Trifluoroacetic acid (PubChem CID: 6422) SP - 80 EP - 8 JF - Carbohydrate research JO - Carbohydr Res VL - 433 N2 - Five sulfated oligosaccharide fragments, F1-F5, were prepared from a pyruvylated galactan sulfate from the green alga Codium divaricatum, by partial depolymerization using mild acid hydrolysis and purification with gel-permeation chromatography. Negative-ion electrospray tandem mass spectrometry with collision-induced dissociation (ES-CID-MS/MS) is attempted for sequence determination of the sulfated oligosaccharides. The sequence of F1 with homogeneous disaccharide composition was first characterized to be Galp-(4SO4)-(1 → 3)-Galp by detailed nuclear magnetic resonance spectroscopic analyses. The fragmentation pattern of F1 in the product ion spectra was established on the basis of negative-ion ES-CID MS/MS, which was then applied to sequence analysis of other sulfated oligosaccharides. The sequences of F2 and F3 were deduced to be Galp-(4SO4)-(1 → 3)-Galp-(1 → 3)-Galp-(1 → 3)-Galp and 3,4-O-(1-carboxyethylidene)-Galp-(6SO4)-(1 → 3)-Galp, respectively. The sequences of major fragments in F4 and F5 were also deduced. The investigation demonstrated that negative-ion ES-CID-MS/MS was an efficient method for the sequence analysis of the pyruvylated galactan sulfate-derived oligosaccharides which revealed the patterns of substitution and glycosidic linkages. The pyruvylated galactan sulfate-derived oligosaccharides were novel sulfated oligosaccharides different from other algal polysaccharide-derived oligosaccharides. SN - 1873-426X UR - https://www.unboundmedicine.com/medline/citation/27471831/Sequence_analysis_of_the_pyruvylated_galactan_sulfate_derived_oligosaccharides_by_negative_ion_electrospray_tandem_mass_spectrometry_ DB - PRIME DP - Unbound Medicine ER -