Glycobiology vol 7 no 3 pp. 421-432, 1997
© 1997
research-article |
New sialic acids from biological sources identified by a comprehensive and sensitive approach: liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) of SIA quinoxalinones
INSERM Unitè 377 1 Place de Verdun. 59045 Lille Cedex, France
1Glycobiology Program, Cancer Center, School of Medicine, University of California San Diego 9500 Gilman Drive, La Jolla. CA 92093-0687, USA
2To whom correspondence should be addressed at: Cancer Center 0687, UCSD School of Medicine, La Jolla, CA 92093–0687, USA
Received on September 17, 1996; revised on November 21, 1996; accepted on November 22, 1996
Sialic acids are a family of 9-carbon carboxylated sugars, where different substitutions of the backbone define over 30 members. Biological roles of these substitutions have been missed until recently because of their low abundance and lability to conventional isolation/purification methods. This new approach characterizes sialic acids using electrospray ionization-mass spectrometry (ESI-MS) to monitor the HPLC separation of their DMB (1,2-diamino-4,5-methylenedioxy-benzene) derivatives (quinoxalinones). A combination of retention times and spectra characteristics allows definition of the type and position of the various substituents. This approach requires no previous purification, involving a simple derivatization reaction followed by direct injection on the microbore HPLC column. A complete spectrum, including molecular ions and CAD fragments of a sialic acid qainoxalinone, is obtained by injecting 10–20 pmol of the compound. Individual quinoxalinones can be purified by regular RP-HPLC and analyzed by direct-injection ESI-MS or LSIMS. Using this approach, we identified 28 different sialic acids, including the following new species: Neu5Gc9Lt (BSM), anhydro derivatives of Neu5Ac other than the 4,8-anhydro (horse serum hydrolyzates), KDNS(7)Ac and KDN5(7),9Ac2 (amphibian Pleurodeles waltl), four isomers of Neu5Gc8MexAc and three anhydro derivatives of Neu5Gc8MS (glycolipids of the starfish Pisaster brevirpinus), and Neu5Ac8S (in addition to Neu5Gc8S, in the glycolipids of the sea urchin Lovenia cordiformis). Results show the usefulness of LC-ESIMS to study sialic acid diversity, and identification of small amounts of unexpected sialic acids or new members of their family.
sialic acid purification electrospray ionizationmass spectrometry quinoxalinone
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