Glycobiology, Vol 8, 685-694, Copyright © 1998 by Society for Glycobiology
KR Anumula and ST Dhume
Facile labeling of oligosaccharides (acidic and neutral) in a nonselective
manner was achieved with highly fluorescent anthranilic acid (AA,
2-aminobenzoic acid) (more than twice the intensity of 2- aminobenzamide,
AB) for specific detection at very high sensitivity. Quantitative labeling
in acetate-borate buffered methanol (approximately pH 5.0) at 80 degreesC
for 60 min resulted in negligible or no desialylation of the
oligosaccharides. A high resolution high performance liquid chromatographic
method was developed for quantitative oligosaccharide mapping on a
polymeric-NH2bonded (Astec) column operating under normal phase and anion
exchange (NP-HPAEC) conditions. For isolation of oligosaccharides from the
map by simple evaporation, the chromatographic conditions developed use
volatile acetic acid-triethylamine buffer (approximately pH 4.0) systems.
The mapping and characterization technology was developed using well
characterized standard glycoproteins. The fluorescent oligosaccharide maps
were similar to the maps obtained by the high pH anion-exchange
chromatography with pulsed amperometric detection (HPAEC-PAD), except that
the fluorescent maps contained more defined peaks. In the map, the
oligosaccharides separated into groups based on charge, size, linkage, and
overall structure in a manner similar to HPAEC-PAD with contribution of
-COOH function from the label, anthranilic acid. However, selectivity of
the column for sialic acid linkages was different. A second dimension
normal phase HPLC (NP-HPLC) method was developed on an amide column (TSK
Gel amide-80) for separation of the AA labeled neutral complex type and
isomeric structures of high mannose type oligosaccharides. The
oligosaccharides labeled with AA are compatible with biochemical and
biophysical techniques, and use of matrix assisted laser desorption mass
spectrometry for rapid determination of oligosaccharide mass map of
glycoproteins is demonstrated. High resolution of NP-HPAEC and NP-HPLC
methods combined with mass spectrometry (MALDI-TOF) can provide an
effective technology for analyzing a wide repertoire of oligosaccharide
structures and for determining the action of both transferases and
glycosidases.
ORIGINAL ARTICLES
High resolution and high sensitivity methods for oligosaccharide mapping and characterization by normal phase high performance liquid chromatography following derivatization with highly fluorescent anthranilic acid
Bioanalytical Sciences Dept., UW2951, Research and Development, SmithKline Beecham Pharmaceuticals, King of Prussia, PA 19406, USA.
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