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ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES BY MATRIX-ASSISTED LASER DESORPTION/IONIZATION MASS SPECTROMETRY:AN UPDATE FOR THE PERIOD 2005–2006

David J.Harvey*

Department of Biochemistry,Oxford Glycobiology Institute,

University of Oxford,Oxford OX13QU,UK

Received 01December 2008;received (revised)26June 2009;accepted 13July 2009

Published online in Wiley InterScience (http://www.doczj.com/doc/75ecfebc960590c69ec376c7.html )DOI 10.1002/mas.20265

This review is the fourth update of the original review,published

in 1999,on the application of MALDI mass spectrometry to the

analysis of carbohydrates and glycoconjugates and brings

coverage of the literature to the end of 2006.The review covers

fundamental studies,fragmentation of carbohydrate ions,

method developments,and applications of the technique to the

analysis of different types of carbohydrate.Specific compound

classes that are covered include carbohydrate polymers from

plants,N-and O-linked glycans from glycoproteins,glycated

proteins,glycolipids from bacteria,glycosides,and various other

natural products.There is a short section on the use of MALDI-

TOF mass spectrometry for the study of enzymes involved in

glycan processing,a section on industrial processes,particularly

the development of biopharmaceuticals and a section on the use

of MALDI–MS to monitor products of chemical synthesis of

http://www.doczj.com/doc/75ecfebc960590c69ec376c7.html rge carbohydrate–protein complexes and

glycodendrimers are highlighted in this final section.#2010

Wiley Periodicals,Inc.,Mass Spec Rev

Keywords:MALDI;carbohydrates;glycoproteins;glycolipids

I.INTRODUCTION

This review is a continuation of the four earlier ones in this series

(Harvey,1999,2006,2009)on the application of MALDI

mass spectrometry to the analysis of carbohydrates and

glycoconjugates and is intended to bring the coverage of the

literature to the end of 2006.MALDI continues to be a major

technique for the analysis of carbohydrates although electrospray

is becoming increasingly popular.Figure 1shows the year-by-

year increase in articles reporting use of MALDI for the period

1991–2006.As the review is designed to complement the earlier

work,structural formulae,etc.that were presented earlier are not

repeated.However,a citation to the structure in the earlier work is

indicated by its number with the prefix ‘‘1’’(i.e.,1/x refers to

structure x in the first review and 2/x to the second).Other reviews

and review-type articles directly concerned with,or including

MALDI analysis of glycoconjugates to have been published

during the review period include general reviews on miniatur-

ized separation techniques including LC/MALDI-TOF/TOF (Mechref &Novotny,2006),solid-phase tools such as micro-arrays (Larsen et al.,2006),capillary electrophoresis-MS (Campa et al.,2006;Huck et al.,2006),atmospheric pressure MALDI (Creaser &Ratcliffe,2006).More specific reviews include those on the analysis of polysaccharides (Cui,2005),glycoproteins and attached glycans (Aitken,2005;Morelle &Michalski,2005;Budnik,Lee,&Steen,2006;Geiser,Silvescu,&Reinhold,2006;Geyer &Geyer,2006;Harvey,Dwek,&Rudd,2006;Haslam,Khoo,&Dell,2006a;Haslam,North,&Dell,2006b;Kondo et al.,2006;Morelle et al.,2006a),N -(Harcum,2005;Harvey,2005d,e;Medzihradszky,2005;Bardor et al.,2006;Jang-Lee et al.,2006)and O -linked (Peter-Katalinic,2005)glycosylation,bacterial glycoproteomics (Hitchen &Dell,2005),protein glycation (Lapolla et al.,2006;Niwa,2006;Silva ´n et al.,2006),GPI anchors (Baldwin,2005),proteoglycans (Didraga,Barroso,&Bischoff,2006),glycosyla-minoglycans (Gama &Hsieh-Wilson,2005;Pojasek,Raman,&Sasisekharan,2005;Sasisekharan et al.,2006),glycosphingoli-pids (Levery,2005;Zheng,Wu,&Hancock,2006b),and flavonoids (de Rijke et al.,2006).The book on mass spectrometry in biophysics by Kaltashov and Eyles (2005)also contains information.II.THEORY Knochenmuss (2006)has summarized ion formation mecha-nisms in UV MALDI and emphasized that a two-step mechanism of ionization during or shortly after the laser pulse,followed by secondary reactions in the expanding plume of desorbed material is gaining acceptance.He concludes by saying that:‘‘To the extent that local thermal equilibrium is approached in the plume,the mass spectra may be straightforwardly interpreted in terms of charge transfer thermodynamics.’’Gas-phase cationization has been demonstrated in an experiment in which two target spots were prepared and illuminated simultaneously with the laser.One spot contained polyethylene glycol (PEG)and dihydroxybenzoic acid (DHB,1/26),whereas the other contained DHB and lithium hydroxide.Even though the PEG and lithium did not come into contact on the

target,[M þLi]þions were observed in the spectrum.However,

because of difficulties in removing residual Na þand K þfrom the

DHB,the authors cou
ld not conclude that gas-phase cationization

DHB,the authors could not conclude that gas-phase cationization

was the only or major process operating under normal MALDI

conditions (Erb,Hanton,&Owens,2006).Mass Spectrometry Reviews

#2010by Wiley Periodicals,Inc.————*Correspondence to:David J.Harvey,Department of Biochemistry,Oxford Glycobiology Institute,University of Oxford,Oxford OX1

3QU,UK.E-mail:david.harvey@bioch.ox.ac.uk

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