Abstract
Synthetic cell wall oligosaccharides are promising molecular tools for investigating the structure and function of plant cell walls. Their well-defined structure and high purity prevents misinterpretations of experimental data, and the possibility to introduce chemical handles provides means for easier localization and detection. Automated glycan assembly as emerged has a powerful new method for the efficient preparation of oligosaccharide libraries. We recently made use of this technology to prepare a collection of plant cell wall glycans for cell wall research. In this chapter, detailed experimental procedures for the automated synthesis of oligosaccharides that are ready for use in biological assays are described.
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References
Albersheim P, Darvill A, Roberts K, Sederoff R, Staehelin A (2011) In: Masson S (ed) Plant cell walls. Taylor and Francis Publishing Group, LLC, Abington
Falk A, Price NJ, Raikhel NV, Keegstra K (2002) An Arabidopsis gene encoding an α-xylosyltransferase involved in xyloglucan biosynthesis. Proc Natl Acad Sci 99:7797–7802
Sampedro J, Pardo B, Gianzo C, Guitian E, Revilla G, Zarra I (2010) Lack of α-xylosidase activity in Arabidopsis alters xyloglucan composition and results in growth defects. Plant Physiol 154:1105–1115
Pedersen HL, Fangel JU, McCleary B, Ruzanski C, Rydahl MG, Ralet MC, Farkas V, von Schantz L, Marcus SE, Andersen MC, Field R, Ohlin M, Knox JP, Clausen MH, Willats WG (2012) Versatile high resolution oligosaccharide microarrays for plant glycobiology and cell wall research. J Biol Chem 287(47):39429–39438
Boltje TJ, Buskas T, Boons GJ (2009) Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research. Nat Chem 1(8):611–622
Kolarich D, Lepenies B, Seeberger PH (2012) Glycomics, glycoproteomics and the immune system. Curr Opin Chem Biol 16(1–2):214–220
Nakahara Y, Ogawa T (1990) Stereoselective total synthesis of dodecagalacturonic acid, a phytoalexin elicitor of soybean. Carbohydr Res 205:147–159
Scanlan EM, Mackeen MM, Wormald MR, Davis BG (2010) Synthesis and solution-phase conformation of the RG-1 fragment of the plant polysaccharide pectin reveals a modification-modulated assembly mechanism. J Am Chem Soc 132:7238–7239
Rao Y, Buskas T, Albert A, O'Neill MA, Hahn MG, Boons GJ (2008) Synthesis and immunological properties of a tetrasaccharide portion of the B side chain of rhamnogalacturonan II (RG-II). ChemBioChem 9(3):381–388
Clausen M, Madsen R (2004) Synthesis of oligogalacturonates conjugated to BSA. Carbohydr Res 339(13):2159–2169
Frechet JM, Schuerch C (1971) Solid-phase synthesis of oligosaccharides. I. Preparation of the solid support. Poly[p-(1-propen-3-ol-1-yl)styrene]. J Am Chem Soc 93:492–496
Seeberger PH, Haase W-C (2000) Solid-phase oligosaccharide synthesis and combinatorial carbohydrate libraries. Chem Rev 100:4349–4393
Seeberger PH (ed) (2001) Solid support oligosaccharide synthesis and combinatorial carbohydrate libraries. Wiley-VCH, New York, NY
Bennett CS (2014) Principles of modern solid-phase oligosaccharide synthesis. Org Biomol Chem 12:1686–1698
Kröck L, Esposito D, Castagner B, Wang C-C, Bindschädler P, Seeberger PH (2012) Streamlined access to conjugation-ready glycans by automated synthesis. Chem Sci 3:1617–1622
Seeberger PH (2008) Automated oligosaccharide synthesis. Chem Soc Rev 37:19–28
Seeberger PH (2015) The logic of automated glycan assembly. Acc Chem Res 48:1450–1463
Plante OJ, Palmacci ER, Seeberger PH (2001) Automated solid-phase synthesis of oligosaccharides. Science 291:1523–1527
Schmidt D, Schuhmacher F, Geissner A, Seeberger PH, Pfrengle F (2015) Automated synthesis of arabinoxylan-oligosaccharides enables characterization of antibodies that recognize plant cell wall glycans. Chem Eur J 21:5709–5713
Senf D, Ruprecht C, de Kruijff GHM, Simonetti SO, Schuhmacher F, Seeberger PH, Pfrengle F (2017) Active site-mapping of xylan-deconstructing enzymes with Arabinoxylan oligosaccharides produced by automated glycan assembly. Chem Eur J 23:3197–3205
Bartetzko MP, Schuhmacher F, Hahm HS, Seeberger PH, Pfrengle F (2015) Automated glycan assembly of oligosaccharides related to Arabinogalactan proteins. Org Lett 17:4344–4347
Bartetzko MP, Schuhmacher F, Seeberger PH, Pfrengle F (2017) Determining substrate specificities of β1,4-endo-galactanases using plant Arabinogalactan oligosaccharides synthesized by automated glycan assembly. J Org Chem 82:1842–1850
Dallabernardina P, Schuhmacher F, Seeberger PH, Pfrengle F (2016) Automated glycan assembly of xyloglucan oligosaccharides. Org Biomol Chem 14:309–313
Dallabernardina P, Ruprecht C, Smith PJ, Hahn MG, Urbanowicz BR, Pfrengle F (2017) Automated glycan assembly of galactosylated xyloglucan oligosaccharides and their recognition by plant cell wall glycan-directed antibodies. Org Biomol Chem 15:9996–10000
Dallabernardina P, Schuhmacher F, Seeberger PH, Pfrengle F (2017) Mixed-linkage glucan oligosaccharides produced by automated glycan assembly serve as tools to determine the substrate specificity of lichenase. Chem Eur J 23:3191–3196
Bartetzko MP, Pfrengle F (2019) Automated glycan assembly of plant oligosaccharides and their application in cell wall biology. ChemBioChem 20:877–885
Ruprecht C, Bartetzko MP, Senf D, Dallabernadina P, Boos I, Andersen MCF, Kotake T, Knox JP, Hahn MG, Clausen MH, Pfrengle F (2017) A synthetic glycan microarray enables epitope mapping of plant cell wall glycan-directed antibodies. Plant Physiol 175:1094–1104
Hahm HS, Schuhmacher F, Seeberger PH (2016) Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages. Nat Chem 7:12482
Eller S, Collot M, Yin J, Hahm HS, Seeberger PH (2013) Automated solid-phase synthesis of chondroitin sulfate glycosaminoglycans. Angew Chem Int Ed 52:5858–5861
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Pfrengle, F. (2020). Automated Glycan Assembly of Plant Cell Wall Oligosaccharides. In: Popper, Z. (eds) The Plant Cell Wall. Methods in Molecular Biology, vol 2149. Humana, New York, NY. https://doi.org/10.1007/978-1-0716-0621-6_28
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DOI: https://doi.org/10.1007/978-1-0716-0621-6_28
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