SialoGlyco Chemistry and Biology II: Tools and Techniques to Identify and Capture Sialoglycans PDF
Preview SialoGlyco Chemistry and Biology II: Tools and Techniques to Identify and Capture Sialoglycans
Topics in Current Chemistry 367 Rita Gerardy-Schahn Philippe Delannoy Mark von Itzstein Editors SialoGlyco Chemistry and Biology II Tools and Techniques to Identify and Capture Sialoglycans 367 Topics in Current Chemistry Editorial Board: H. Bayley, Oxford, UK K.N. Houk, Los Angeles, CA, USA G. Hughes, CA, USA C.A. Hunter, Sheffield, UK K. Ishihara, Chikusa, Japan M.J. Krische, Austin, TX, USA J.-M. Lehn, Strasbourg Cedex, France R. Luque, C(cid:1)ordoba, Spain M. Olivucci, Siena, Italy J.S. Siegel, Tianjin, China J. Thiem, Hamburg, Germany M. Venturi, Bologna, Italy C.-H. Wong, Taipei, Taiwan H.N.C. Wong, Shatin, Hong Kong V.W.-W. Yam, Hong Kong, China S.-L. You, Shanghai, China Aims and Scope TheseriesTopicsinCurrentChemistry presentscriticalreviews ofthepresent and futuretrendsinmodernchemicalresearch.Thescopeofcoverageincludesallareasof chemical science including the interfaces with related disciplines such as biology, medicineandmaterialsscience. Thegoalofeachthematicvolumeistogivethenon-specialistreader,whetheratthe universityorinindustry,acomprehensiveoverviewofanareawherenewinsightsare emergingthatareofinteresttolargerscientificaudience. Thuseachreviewwithinthevolumecriticallysurveysoneaspectofthattopicand places it within the context of the volume as a whole. The most significant developments of the last 5 to 10 years should be presented. A description of the laboratoryproceduresinvolvedisoftenusefultothereader.Thecoverageshouldnot be exhaustive in data, but should rather be conceptual, concentrating on the methodological thinking that will allow the non-specialist reader to understand the informationpresented. Discussionofpossiblefutureresearchdirectionsintheareaiswelcome. Reviewarticlesfortheindividualvolumesareinvitedbythevolumeeditors. Readership:researchchemistsatuniversitiesorinindustry,graduatestudents. Moreinformationaboutthisseriesat http://www.springer.com/series/128 Rita Gerardy-Schahn (cid:129) Philippe Delannoy (cid:129) Mark von Itzstein Editors SialoGlyco Chemistry and Biology II Tools and Techniques to Identify and Capture Sialoglycans With contributions by (cid:1) (cid:1) (cid:1) (cid:1) (cid:1) B. Ernst J. Finne K. Fukase G. Herrler J. Hirabayashi (cid:1) (cid:1) (cid:1) (cid:1) C.-H. Hsu E. Jakobsson A. Jokilammi S. Kelm (cid:1) (cid:1) (cid:1) (cid:1) K. Kitajima H.D. Klenk A. Kuno C.-H. Liang (cid:1) (cid:1) (cid:1) (cid:1) M. Matrosovich S. Meinke C. Sato O. Schwardt (cid:1) (cid:1) (cid:1) (cid:1) D. Schwarzer K. Tanaka H. Tateno J. Thiem (cid:1) N. Varki C.-Y. Wu Editors RitaGerardy-Schahn PhilippeDelannoy InstituteforCellularChemistry LilleUniversityofScienceandTechnology Hannover,Germany Villeneuved’AscqCedex,France MarkvonItzstein InstituteforGlycomics GriffithUniversity Southport,Queensland Australia ISSN0340-1022 ISSN1436-5049 (electronic) TopicsinCurrentChemistry ISBN978-3-319-21316-3 ISBN978-3-319-21317-0 (eBook) DOI10.1007/978-3-319-21317-0 LibraryofCongressControlNumber:2015944515 SpringerChamHeidelbergNewYorkDordrechtLondon ©SpringerInternationalPublishingSwitzerland2015 Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpartof the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilarmethodologynowknownorhereafterdeveloped. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publicationdoesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexempt fromtherelevantprotectivelawsandregulationsandthereforefreeforgeneraluse. Thepublisher,theauthorsandtheeditorsaresafetoassumethattheadviceandinformationinthis book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained hereinorforanyerrorsoromissionsthatmayhavebeenmade. Printedonacid-freepaper Springer International Publishing AG Switzerland is part of Springer Science+Business Media (www.springer.com) Preface Nature’s enormous potential for the shaping of structures is made possible by the use ofsugars.1These molecular buildingblocksare uniqueinprovidingpermuta- tion capacity. From a chemical point of view, sugars are polyhydroxy-aldehydes and -ketones which, under physiological conditions, form ring structures (hemi- acetals).Therelativepositionofhydroxylgroups(OH–groups)totheplaneofthe cyclic scaffold determines their chemical and biological properties. For instance, sugars with distinct biological functions such as glucose and galactose differ chemically in no more than the relative positioning of a single OH– group. Moreover, sugars are multivalent and, because of the anomeric freedom of the reducing end, can generate α- or β-linkages to any one of several positions on a secondmonosaccharide.Thus,thetheoreticalnumberofdistincttrisaccharidesthat canbebuiltbythecombinationof3monosaccharidescanreach27,648whereas3 differentnucleotidesoraminoacidscanformonly6trimers(forreviewsee[1]). Sialic acids are acidic nine-carbon sugars that meet all the above discussed aspectsandarespecialbecausetheadditionofsialicacidtoglycoconjugatesoccurs exclusively at the non-reducing end. Because of this ‘outstanding’ position, sialoglycoconjugates form the‘communication front’ of animal cells. Mandal and colleaguesreviewthisrichnessofthesialomewithafocusontheO-acetylationof sialic acids. O-Acetylation represents a developmentally regulated modification and a marker of some cancer cells such as lymphoblasts in acute lymphoblastic leukemia. In terms of evolution, sialic acids have an interestinghistory withan abundant occurrence in the deuterostome lineage and a scattered expression in bacterial pathogens.Importantly,virusesinfectingthesebacteriabearhighlyspecificrecep- tors recognizing the bacterial sialoglycans. In fact, the use of these unique viral toolsinbiochemistrylaboratorieshasbeenofenormousvalueforthedetectionand characterization of sialoglycans, as is discussed by Jakobsson and colleagues 1Thetermissynonymouslyusedwiththetermcarbohydrates. v vi Preface (seethechaptertitled “Endosialidases: VersatileToolsfor theStudy ofPolysialic Acid”).Moreover,asreviewedbyMatrosovichandcolleagues,manyviralpatho- gensrecognizeandintrudeontheirhostsbyexploitingcellularsialoglycans(seethe chaptertitled“SialicAcidReceptorsofViruses”). Anorganparticularlyrichinsialoglycansisthebrain.Asextensivelyreviewed by Hildebrandt and Dityatev, a large number of reports has demonstrated the essential nature of sialic acid for brain development and function. While the major form of sialic acid in humans is N-acetyl-neuraminic acid (Neu5Ac), most vertebrates, including the great apes, produce N-glycolyl-neuraminic acid (Neu5Gc) at similar or even higher concentrations. However, remarkably, in species where Neu5Gc represents the major sialic acid in peripheral tissues, Neu5Gcisrarelyfoundinbrainstructures,thusraisingthequestionastowhether Neu5Gc could be toxic in the brain (see the review by Davies and Varki). In the lightofevolution,thistissue-selectiveexpulsionofNeu5Gcisexcitingbecausethe gene encoding the hydroxylase needed for the conversion of CMP-Neu5Ac to CMP-Neu5Gc was lost before the emergence of the genus Homo. However, humans can acquire Neu5Gc from dietary sources and a number of studies have shown the presence of Neu5Gc in peripheral tissues. Whether the integration of Neu5Gc into human tissue causes major immune reactions is a matter of debate. Shilova et al. present a primary study in this volume, in which large cohorts of probandswere screened fortheirpatterns ofnaturalantibodies.Surprisingly,only lowconcentrationsofnaturalantibodiesagainstsialoglycanswereidentified. Thecloningofthemajorcomponentsofthesialylationmachineryinmammals generatednewtargetsforthegenerationofknockoutmodelswhichhavebeenused to interrogate the role of sialic acids and sialoglycans in organ development and homeostasis. The lessons learned by the use of these mouse models to re-enact sialoglyco pathologies identified in humans are reviewed by Hinderlich and col- leaguesandSellmeierandcolleagues. Control of sialoglycoconjugate expression in the mammalian system involves theactivityofsialidasesaswellasanabolicpathways.Theinterestinthisimportant group of enzymes was underestimated in the past but is currentlyescalating. This volumeisdirectingmajorattentiontothesedevelopmentsbyprovidingadetailed review on structure-function and phylogenetic analyses prepared by Monti and Miyagi. Consideringthattheoutsideoftheanimalcellsisdominatedbythepresenceof sialoglycans, it is not difficult to deduce that there must be numerous counter- receptors to decipher the information presented in the sialome. This fact requests bothnovelanalyticaltechniquespermittingthequantitativedeterminationofindi- vidual glycotopes and techniques that allow a holistic monitoring of variations in the cellular sialome such as those occurring during cell differentiation or in cancerogenesis. This analytical area has generated a new research field which is reviewed in this volume by outstanding experts (Kitajima et al., see the chapter titled “Advanced Technologies in Sialic Acid and Sialoglycoconjugate Analysis” andHirabayashietal.,seethechaptertitled“DevelopmentandApplicationsofthe Lectin Microarray”). The search for proteins (factors in general) that specifically Preface vii bind to sialoglycans is a success story that impressively demonstrates the added value of interdisciplinary collaborative research activities in the field of glycobiology.Innovativearraytechnologiesdevelopedbysyntheticorganicchem- istshavepavedthewayforthesearchofbindingmoleculesnotonlyatthecellular levelbutalsosystematically.Thesetopicsarereviewedinthreedifferentchapters byLiang etal.(seethe chaptertitled“Sialoside Arrays: New Synthetic Strategies andApplications”),TanakaandFukase(seethechaptertitled“ChemicalApproach to a Whole Body Imaging of Sialo-N-Linked Glycans”), and Meinke and Thiem (see the chapter titled “Trypanosomal Trans-sialidases: Valuable Synthetic Tools andTargetsforMedicinalChemistry”).Last,butcertainlynotleast,Schwadtetal. (see the chapter titled “SIGLEC-4 (MAG) Antagonists: From the Natural Carbo- hydrateEpitopetoGlycomimetics”)focusonthespecificityofsialylatedcarbohy- drate structures and the development of sialic acid derivatives that mimic these structures.Withmyelin-associatedglycoprotein(MAG)asanexample,thedevel- opmentofmimetics thatbind with lownanomolaraffinityis described.Theleads identified show great promise to be developed further to prevent the inhibitory activityofMAGonnerveregeneration. This edition entitled SialoGlyco Chemistry and Biology I and SialoGlyco Chemistry and Biology II combines 15 chapters from distinguished authors that, together, form a unique reference book which should be of great interest to researchersandteachers. Hannover,Germany RitaGerardy-Schahn Villeneuved’AscqCedex,France PhilippeDelannoy Southport,Australia MarkvonItzstein Reference 1.CohenM,VarkiA(2010)OMICS14(4):455–464.doi:10.1089/omi.2009.0148 ThiSisaFMBlankPage Contents SialicAcidReceptorsofViruses. . .. . . .. . . .. . . .. . . .. . . .. . . .. . . 1 MikhailMatrosovich,GeorgHerrler,andHansDieterKlenk Endosialidases:VersatileToolsfortheStudyofPolysialicAcid. . . . . 29 ElinaJakobsson,DavidSchwarzer,AnneJokilammi,andJukkaFinne AdvancedTechnologiesinSialicAcidandSialoglycoconjugate Analysis. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75 KenKitajima,NissiVarki,andChihiroSato DevelopmentandApplicationsoftheLectinMicroarray. . . . . . . . . . . 105 JunHirabayashi,AtsushiKuno,andHiroakiTateno SialosideArrays:NewSyntheticStrategiesandApplications. . . . . . . 125 Chi-HuiLiang,Che-HsiungHsu,andChung-YiWu SIGLEC-4(MAG)Antagonists:FromtheNaturalCarbohydrate EpitopetoGlycomimetics. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 151 OliverSchwardt,SoergeKelm,andBeatErnst ChemicalApproachtoaWholeBodyImagingofSialo-N-Linked Glycans. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 201 KatsunoriTanakaandKoichiFukase TrypanosomalTrans-sialidases:ValuableSyntheticTools andTargetsforMedicinalChemistry. . . . . . . . . . . . . . . . . . . . . . . . . 231 SebastianMeinkeandJoachimThiem Index. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 251 ix
The list of books you might like
