title: Sequence analysis of the pyruvylated galactan sulfate-derived oligosaccharides by negative-ion electrospray tandem mass spectrometry.
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.
authors.affiliation: 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.
authors.forename: Na
authors.initials: N
authors.lastname: Li
authors.affiliation: 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.
authors.forename: Wenjun
authors.initials: W
authors.lastname: Mao
authors.affiliation: 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.
authors.forename: Xue
authors.initials: X
authors.lastname: Liu
authors.affiliation: 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.
authors.forename: Shuyao
authors.initials: S
authors.lastname: Wang
authors.affiliation: 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.
authors.forename: Zheng
authors.initials: Z
authors.lastname: Xia
authors.affiliation: 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.
authors.forename: Sujian
authors.initials: S
authors.lastname: Cao
authors.affiliation: 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.
authors.forename: Lin
authors.initials: L
authors.lastname: Li
authors.affiliation: 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.
authors.forename: Qi
authors.initials: Q
authors.lastname: Zhang
authors.affiliation: 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.
authors.forename: Shan
authors.initials: S
authors.lastname: Liu
mesh_terms: D002240:Carbohydrate Sequence; D005685:Galactans / Q000737:chemistry; D009844:Oligosaccharides / Q000032:analysis* / Q000737:chemistry; D011773:Pyruvates / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D013431:Sulfates / Q000737:chemistry*; D053719:Tandem Mass Spectrometry
chemical_list: D005685:Galactans; D009844:Oligosaccharides; D011773:Pyruvates; D013431:Sulfates
keywords: 1-Phenyl-3-methyl-5-pyrazolone (PubChem CID: 90474051); Acetonitrile (PubChem CID: 6342); Ammonium bicarbonate (PubChem CID: 14013); Barium rhodizonic acid (PubChem CID: 45048930); Codium divaricatum; D-galactose (PubChem CID: 6036); Deuterium oxide (PubChem CID: 24602); ES-CID-MS/MS; Oligosaccharides; Potassium bromide (PubChem CID: 253877); Pyruvylated galactan sulfate; Sequence; Sodium hydroxide (PubChem CID: 14798); Sulfuric acid (PubChem CID: 1118); Trifluoroacetic acid (PubChem CID: 6422)