Application of Electrospray Tandem Mass Spectrometry in Sequence Analysis of Oligosaccharides†

doi:10.7503/cjcu20140629

Abstract

Abstract:

Analysis of oligosaccharide structure and sequence plays a significant role in unravelling the biolo-gical function of glycoconjugates. Electrospray ionization mass spectrometry(ESI-MS) is an important tool for the qualitative and quantitative analysis of oligosaccharides with high sensitivity, high precision and high speed. Some oligosaccharides with different structural characteristics, such as N-glycans, chondroitin sulfate oligosaccharides, human milk oligosaccharides, chitooligosaccharide, alginate oligosaccharides, carrageenan oligosaccharides and sulfated fucan oligosaccharides are discussed in this paper. The application techniques of ESI-MS and fragmentation rule of oligosaccharides in the sequence analysis of the main chain, branch sites, substitution positions of sulfate groups, as well as the monosaccharide composition and the degree of polymerization are summarized. The types of monosaccharide composition can be obtained primarily based on the adjacent m/z difference of B/C fragment ions. The resolution and ionization efficiency of oligosaccharides can be improved by combination with chromatography separation techniques or derivatization methods, and then the molecular weight and degree of polymerization of oligosaccharides can be measured. The information of redu-cing residue and partial sequence of oligosaccharides can be obtained by means of tandem mass spectrometry and characterized derivatization of the reducing end. The types and particular locations of residues can be determined according to their specific fragment ions and abundance. In addition, the branches of oligosaccharide usually occur glycoside bond breakage as a unit or produce D ions, which can be used to determine the branch points. The sulfate groups in different sites can be obtained by their specific cross-ring fragments. The summarization of fragmentation rule of oligosaccharides in ESI-MS provides a guidance to the structure and sequence analysis of unknown oligosaccharides.

Key words: Electrospray ionization mass spectrometry, Oligosaccharide, Fragmentation rule, Sequence analysis

CLC Number:

O629
O657

TrendMD:

CHEN Huanhuan, ZHAO Xia, LUAN Xiaohong, YU Guangli. Application of Electrospray Tandem Mass Spectrometry in Sequence Analysis of Oligosaccharides^†[J]. Chem. J. Chinese Universities, 2015, 36(1): 1.

Figures/Tables 5

References 59

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Monosaccharide species	Molecular formula	Molecular weight	m/z Difference of the adjacent B/C fragmentation	Possible monosaccharides
Hexose	C₆H₁₂O₆	180	162	Glucose(Glc), mannose(Man), galactose(Gal), fructose(Fru)
Methyl pentose	C₆H₁₂O₅	164	146	Rhamnose(Rha), fucose(Fuc)
Anhydro-hexose	C₆H₁₀O₅	162	144	3,6-Anhydro-galactose(A)
Pentose	C₅H₁₀O₅	150	132	Ribose(Rib), arabinose(Ara), xylose(Xyl), lyxose(Lyx)
Hexuronic acid	C₆H₁₀O₇	194	176	Glucuronide(GlcA), galacturonic acid(GalA)
Hexosamine	C₆H₁₃NO₅	179	161	Glucosamine(GlcN), galactosamine(GalN)
Acetylated hexosamine	C₈H₁₅NO₆	221	203	Acetylglucosamine(GlcNAc), acetylgalactosamine(GalNAc)
N-Acetylneuraminic acid(NeuAc)	C₁₁H₁₉NO₉	309	291
N-Glycolylneuraminic acid(NeuGc)	C₁₁H₁₉NO₁₀	325	307

Monosaccharide species	Molecular formula	Molecular weight	m/z Difference of the adjacent B/C fragmentation	Possible monosaccharides
Hexose	C₆H₁₂O₆	180	162	Glucose(Glc), mannose(Man), galactose(Gal), fructose(Fru)
Methyl pentose	C₆H₁₂O₅	164	146	Rhamnose(Rha), fucose(Fuc)
Anhydro-hexose	C₆H₁₀O₅	162	144	3,6-Anhydro-galactose(A)
Pentose	C₅H₁₀O₅	150	132	Ribose(Rib), arabinose(Ara), xylose(Xyl), lyxose(Lyx)
Hexuronic acid	C₆H₁₀O₇	194	176	Glucuronide(GlcA), galacturonic acid(GalA)
Hexosamine	C₆H₁₃NO₅	179	161	Glucosamine(GlcN), galactosamine(GalN)
Acetylated hexosamine	C₈H₁₅NO₆	221	203	Acetylglucosamine(GlcNAc), acetylgalactosamine(GalNAc)
N-Acetylneuraminic acid(NeuAc)	C₁₁H₁₉NO₉	309	291
N-Glycolylneuraminic acid(NeuGc)	C₁₁H₁₉NO₁₀	325	307