Abstract
Densely packed carbohydrate clusters on cell surfaces play essential roles in varieties of bioprocesses. Little information has been, however, accumulated so far concerning their structural/functional details. In this chapter, we discuss artificial systems to investigate carbohydrate-carbohydrate interactions within/between the carbohydrate cluster(s). Among such artificial systems, much attention will be especially placed on glycosylated tris-bipyridine ferrous complexes for monitoring not only carbohydrate-carbohydrate interactions within the glycocluster but also their resultant conformational changes.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Altamore TM, Fernández-García C, Gordon AH, Hübscher T, Promsawan N, Ryadnov MG, Doig AJ, Woolfson DN, Gallagher T (2011) Randomcoil: α-helix equilibria as a reporter for the LewisX–LewisX interaction. Angew Chem Int Ed 50:11167–11171
Chen Q, Cui Y, Zhang T, Cao J, Han B (2010) Fluorescent conjugated polyfluorene with pendant lactopyranosyl ligands for studies of Ca2+- mediated carbohydrate-carbohydrate interaction. Biomacromolecules 11:13–19
de la Fuente JM, Eaton P, Barrientos AG, Menéndez M, Penadés S (2005) Thermodynamic evidence for Ca2+ mediated self-aggregation of Lewis X gold glyconanoparticles. A model for cell adhesion via carbohydrate-carbohydrate interaction. J Am Chem Soc 127:6192–6197
Eggens I, Fenderson B, Toyokuni T, Dean B, Stroud M, Hakomori S (1989) Specific Interaction between Le and Le determinants. J Biol Chem 264:9476–9484
Gege C, Geyer A, Schmidt RR (2002) Carbohydrate-carbohydrate recognition between Lewis X blood group antigens, mediated by calcium ions. Eur J Org Chem 2475:2485
Handa K, Hakomori S (2012) Carbohydrate to carbohydrate interaction in development process and cancer progression. Glycoconj J 29:627–637
Hasegawa T, Sasaki T (2003) Glyco-helix: parallel lactose-lactose interactions stabilize an α-helical structure of multi-glycosylated peptide. Chem Commun 8:978–979
Hasegawa T, Numata M, Asai M, Takeuchi M, Shinkai S (2005) Colorimetric calcium-response of β -lactosylated μ-oxo-bis-[5,15-mesodiphenylporphyrinatoiron(III)]. Tetrahedron 61:7783–7788
Jayaraman N, Maiti K, Naresh K (2013) Multivalent glycoliposomes and micelles to study carbohydrate–protein and carbohydrate–carbohydrate interactions. Chem Soc Rev 42:4640–4656
Lai C, Hütter J, Hsu C, Tanaka H, Varela-Aramburu S, De Cola L, Lepenies B, Seeberger PH (2016) Analysis of carbohydrate−carbohydrate interactions using sugar-functionalized silicon nanoparticles for cell imaging. Nano Lett 16:807–811
Lorenz B, de Cienfuegos LÁ, Oelkers M, Kriemen E, Brand C, Stephan M, Sunnick E, Yüksel D, Kalsani V, Kumar K, Werz DB, Janshoff A (2012) Model system for cell adhesion mediated by weak carbohydrate−carbohydrate interactions. J Am Chem Soc 134:3326–3329
Matsuura K, Kobayashi K (2004) Analysis of GM3-Gg3 interaction using clustered gycoconjugate models constructed from glycolipid monolayers and artificial glycoconjugate polymers. Glycoconj J 21:139–148
Matsuura K, Oda R, Kitakouji H, Kiso M, Kitajima K, Kobayashi K (2004) Surface plasmon resonance study of carbohydrate-carbohydrate interaction between various gangliosides and Gg3-carrying polystyrene. Biomacromolecules 5:937–941
Nonaka Y, Uruno R, Dai F, Matsuoka R, Nakamura M, Iwamura M, Iwabuchi H, Okada T, Chigira N, Amano Y, Hasegawa T (2016) Hexavalent glycoclusters having tris-bipyridine ferrous complex cores as minimum combinatorial libraries for probing carbohydrate-carbohydrate interactions. Tetrahedron 72:5456–5464
Otsuka A, Sakurai K, Hasegawa T (2009) Ferrocenes with two carbohydrate appendages at the upper and lower rings are useful for investigating carbohydrate–carbohydrate interactions. Chem Commun 36:5442–5444
Pincet F, Bouar TL, Zhang Y, Esnault J, Mallet J, Perez E, Sinay P (2001) Ultraweak sugar-sugar interactions for transient cell adhesion. Biophys J 80:1354–1358
Prinetti A, Loberto N, Chigorno V, Sonnino S (2009) Glycosphingolipid behaviour in complex membranes. Biochim Biophys Acta 1788:184–193
Reynolds AJ, Haines AH, Russell DA (2006) Gold glyconanoparticles for mimics and measurement of metal ion-mediated carbohydratecarbohydrate interactions. Langmuir 22:1156–1163
Seah N, Santacroce PV, Basu A (2009) Probing the lactose·GM3 carbohydrate-carbohydrate interaction with glycodendrimers. Org Lett 11:559–562
Simpson GL, Gordon AH, Lindsay DM, Promsawan N, Crump MP, Mulholland K, Hayter BR, Gallagher T (2006) Glycosylated foldamers to probe the carbohydrate−carbohydrate interaction. J Am Chem Soc 128:10638–10639
Yu S, Kojima N, Hakomori S, Kudo S, Inoue S, Inoue Y (2002) Binding of rainbow trout sperm to egg is mediated by strong carbohydrate-to−+carbohydrate interaction between (KDN)GM3 (deaminated neuraminyl ganglioside) and Gg3-like epitope. PNAS 99:2854–2859
Zhao J, Liu Y, Park H, Boggs JM, Basu A (2012) Carbohydrate-coated fluorescent silica nanoparticles as probes for the galactose/3-sulfogalactose carbohydrate−carbohydrate interaction using model systems and cellular binding studies. Bioconjug Chem 12:1166–1173
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2018 Springer Nature Singapore Pte Ltd.
About this chapter
Cite this chapter
Hasegawa, T. (2018). Synthesis of Glycosylated Metal Complexes for Probing Carbohydrate-Carbohydrate Interactions. In: Yamaguchi, Y., Kato, K. (eds) Glycobiophysics. Advances in Experimental Medicine and Biology, vol 1104. Springer, Singapore. https://doi.org/10.1007/978-981-13-2158-0_2
Download citation
DOI: https://doi.org/10.1007/978-981-13-2158-0_2
Published:
Publisher Name: Springer, Singapore
Print ISBN: 978-981-13-2157-3
Online ISBN: 978-981-13-2158-0
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)