HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS		QUICK SEARCH:   [advanced] Author: Keyword(s): Year:  Vol:  Page:

This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Citation Map Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Request Permissions Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Manzi, A. E. Articles by Varki, A. Search for Related Content PubMed PubMed Citation Articles by Manzi, A. E. Articles by Varki, A. Social Bookmarking                      What's this?

J. Biol. Chem., Vol. 265, Issue 14, 8094-8107, May, 1990

Studies of naturally occurring modifications of sialic acids by fast- atom bombardment-mass spectrometry. Analysis of positional isomers by periodate cleavage [published erratum appears in J Biol Chem 1990 Jul 25;265(21):12749]

AE Manzi, A Dell, P Azadi and A Varki
Department of Medicine, San Diego Veterans Medical Center, La Jolla, California.

A variety of modifications of sialic acids have been described in nature. There are currently many difficulties in the detection and quantitation of these modified sialic acids from biological sources. We report here that fast-atom bombardment-mass-spectrometry (FAB-MS) of native sialic acids provides specific detection and quantitation of many previously known compounds. Derivatization of the sialic acids by reduction and peracylation under acidic conditions prior to FAB-MS provides further confirmation of their identity and improves the sensitivity of detection. Samples containing as little as 100 ng of a derivatized sialic acid loaded onto the FAB target allowed accurate identification. Mixtures of sialic acids could be analyzed, and minor components were seen, at levels undetectable by other currently known techniques. Analysis of known mixtures of different sialic acids gave reproducible relative signal intensities, indicating that quantitative data can be derived from the FAB-MS spectra. After reduction and peracylation, each sialic acid gave two major molecular ions, corresponding to the fully derivatized linear species and a lactone form, and a minor ion, corresponding to an anhydro form. Lactone formation was minimal in the case of four substituted sialic acids, indicating that the hydroxyl group at the 4-position is involved in lactonization. Differentiation between different positional isomers of the modified sialic acids could be achieved using controlled degradation with periodate, tagging of the fragments with p- aminobenzoic acid ethyl ester under acid reducing conditions, peracylation, and FAB-MS of the derivatized products. We used this FAB- MS strategy to identify a novel sialic acid, 8-O-methyl-7,9-di-O-acetyl- N-glycolyl-neuraminic acid from the starfish Pisaster brevispinus, and to demonstrate the presence of a previously undetected sialic acid, 4,8- anhydro-N-acetyl-neuraminic acid in acid hydrolysates of horse serum. We also use FAB-MS to show that the alkaline conditions traditionally used for analytical de-O-acetylation of sialic acids causes substantial conversion of 4-O-acetylated sialic acids into the same anhydro compound.
CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    What's this?

This article has been cited by other articles:

				M. L. Warwas, J. N. Watson, A. J. Bennet, and M. M. Moore Structure and role of sialic acids on the surface of Aspergillus fumigatus conidiospores Glycobiology, April 1, 2007; 17(4): 401 - 410. [Abstract] [Full Text] [PDF]

				E. C. M. Brinkman-Van der Linden, T. Angata, S. A. Reynolds, L. D. Powell, S. M. Hedrick, and A. Varki CD33/Siglec-3 Binding Specificity, Expression Pattern, and Consequences of Gene Deletion in Mice Mol. Cell. Biol., June 15, 2003; 23(12): 4199 - 4206. [Abstract] [Full Text] [PDF]

				D. Zhang, J. Takahashi, T. Seno, Y. Tani, and T. Honda Analysis of Receptor for Vibrio cholerae El Tor Hemolysin with a Monoclonal Antibody That Recognizes Glycophorin B of Human Erythrocyte Membrane Infect. Immun., October 1, 1999; 67(10): 5332 - 5337. [Abstract] [Full Text] [PDF]

				Y. C. Barnes, T. P. Skelton, I. Stamenkovic, and D. C. Sgroi Sialylation of the Sialic Acid Binding Lectin Sialoadhesin Regulates Its Ability to Mediate Cell Adhesion Blood, February 15, 1999; 93(4): 1245 - 1252. [Abstract] [Full Text] [PDF]

				M. D. Rolsma, T. B. Kuhlenschmidt, H. B. Gelberg, and M. S. Kuhlenschmidt Structure and Function of a Ganglioside Receptor for Porcine Rotavirus J. Virol., November 1, 1998; 72(11): 9079 - 9091. [Abstract] [Full Text] [PDF]

				M. Krishna and A. Varki 9-O-Acetylation of Sialomucins: A Novel Marker of Murine CD4 T Cells that Is Regulated during Maturation and Activation J. Exp. Med., June 2, 1997; 185(11): 1997 - 2013. [Abstract] [Full Text] [PDF]

				W.-X. Shi, R. Chammas, and A. Varki Linkage-specific Action of Endogenous Sialic Acid O-Acetyltransferase in Chinese Hamster Ovary Cells J. Biol. Chem., June 21, 1996; 271(25): 15130 - 15138. [Abstract] [Full Text] [PDF]

				E. R. Sjoberg, R. Chammas, H. Ozawa, I. Kawashima, K.-H. Khoo, H. R. Morris, A. Dell, T. Tai, and A. Varki Expression of De-N-acetyl-gangliosides in Human Melanoma Cells Is Induced by Genistein or Nocodazole J. Biol. Chem., February 17, 1995; 270(7): 2921 - 2930. [Abstract] [Full Text] [PDF]