Abstract
The realization that the oligosaccharide moieties of glycoconjugates, such as glycoproteins and glycolipids, are involved in important intra- and intercellular of important oligosaccharide structures as tools in analytical and therapeutic studies (see refs. 1 and 2 for reviews). A number of efficient chemical procedures have been developed for the synthesis of the “glyco-” part (see refs. 3–7 for review). However, for the synthesis of a given saccharide structure, an individual strategy has to be set up comprising many laborious protection and deprotection steps for stereo-controlled synthesis, which finally results in only moderate overall yields. As an example, the synthesis of N-acetyllactosamine (LacNAc) involves 12 steps and needs 3 months of lab work (7). A scale-up of the chemical procedure often encounters environmental problems because all steps are carried out in organic solvents.
Keywords
- Enzymatic Synthesis
- Nucleotide Sugar
- Product Solution
- Potassium Acetate
- Product Isolation
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
This is a preview of subscription content, access via your institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsSpringer Nature is developing a new tool to find and evaluate Protocols. Learn more
References
Rademacher, T. W., Parekh, R. B., and Dwek, R. A. (1988) Glycobiology. Annu. Rev. Biochem. 57, 785–838.
Varki, A. (1993) Biological roles of oligosaccharides: all of the theories are correct. Glycobiology 3, 97–130.
Paulsen, H. (1982) Advances in selective chemical synthesis of complex oligosaccharides. Angew. Chem. Int. Ed. Engl. 21, 155–173.
Kondo, H., Aoki, S., Ichikawa, Y., Halcomb, R. L., Ritzen, H., and Wong, C.-H. (1994) Glycosyl phosphites as glycosylation reagents: scope and mechanism. J. Org. Chem. 59, 864–877.
Schmidt, R. R. and Kinzy W. (1994) Anomeric-oxygen activation for glycoside synthesis. The trichloroacetimidate method. Adv. Carbohydr. Chem. Biochem. 50, 21–128.
Garg, H. G., von dem Bruch, K., and Kunz, H. (1994) Developments in the synthesis of glycopeptides containing glycosyl L-asparagine, L-serine and L-threonine. Adv. Carbohydr. Chem. Biochem. 50, 277–310.
Khan, S. H. and Hindsgaul, O. (1994) Chemical synthesis of oligosaccharides, in Frontiers in Molecular Biology, Molecular Glycobiology (Fukuda M. and Hindsgaul O., eds.), IRL, Oxford, pp. 206–229.
Wong, C.-H. and Whitesides, G. M. (1994) Enzymes in Synthetic Organic Chemistry. Elsevier Science, Oxford.
Nilsson, K. G. I. (1996) Synthesis with glycosidases, in Modern Methods in Carbohydrate Synthesis (Khan, S. H. and O’Neill, R. A., eds.), Harwood Academic Publishers, Amsterdam, pp. 518–547.
Palcic M. M. and Hindsgaul, O. (1996) Glycosyltransferases in the synthesis of oligosaccharide analogs. Trends Glycosci. Glycotechnol. 8, 37–49.
Elling, L. (1997) Glycobiotechnology: Enzymes for the synthesis of nucleotide sugars. Adv. Biochem. Eng. Biotechnol. 58, 89–144.
Elling, L. and Kula, M.-R. (1993) Purification of sucrose synthase from rice and its protein-chemical characterization. J. Biotechnol. 29, 277–286.
Elling, L., Güldenberg, B., Grothus, M., Zervosen, A., Péus, M., Helfer, A., Stein, A., et al. (1995) Isolation of sucrose synthase from rice (Oryza sativa) grains in pilot scale for application in carbohydrate synthesis. Biotechnol. Appl. Biochem. 21, 29–37.
Schrader, H. (1998) Phd-thesis, Heimrich Heine University, Drisseldorf, Germany.
Elling, L., Grothus, M., and Kula, M.-R. (1993) Investigation of sucrose synthase from rice for the synthesis of various nucleotide sugars and saccharides. Glycobiology 3, 349–355.
Elling, L. and Kula, M.-R. (1995) Characterization of sucrose synthase from rice grains for the enzymatic synthesis of UDP-and TDP-glucose. Enzyme Microb. Technol. 17, 929–934.
Zervosen, A., Stein, A., Adrian, H., and Elling, L. (1996) Combined enzymatic synthesis of nucleotide (deoxy)sugars from sucrose and nucleoside monophosphates. Tetrahedron 52, 2395–2404.
Stein, A., Kula, M.-R., and Elling, L. (1998) Combined preparative enzymatic synthesis of dTDP-6-deoxy-4-keto-D-glucose from dTDP and sucrose. Glycoconjugate J. 15, 139–145.
Preiss J. (1991) Biology and molecular biology of starch synthesis and its regulation, in Oxford Surveys of Plant Molecular & Cell Biology, vol. 7 (Miflin, B. J., ed.), Oxford University Press, Oxford, pp. 59–114.
Kleczkowski, L. A., Villand, P., Lönneborg, A., Olsen, O.-A., and Ernst, L. (1991) Plant ADP-glucose pyrophosphorylase: recent advances and biotechnological perspectives (a review). Z. Naturforsch. 46c, 605–612.
Preiss, J. and Romeo, T. (1989) Physiology, biochemistry and genetics of bacterial glycogen synthesis. Adv. Microb. Physiol. 30, 183–238.
Zervosen, A. and Elling, L. (1996) A novel three-enzymes-reaction-cycle for the synthesis of N-acetyllactosamine with in situ regeneration of uridine 5′-diphosphate glucose and uridine 5′-diphosphate galactose. J. Am. Chem. Soc. 118, 1836–1840.
Varki, A. (1994) Selectin ligands. Proc. Natl. Acad. Sci. USA 91, 7390–7397.
Montreuil, J., Vliegenthart, J. F. G., and Schachter, H. (eds.) (1995) Glycoproteins. New Comprehensive Biochemistry, vol. 29a. Elsevier, Amsterdam.
Nelsestuen, G. and Kirkwood, S. (1971) The mechanism of action of the uridine diphosphoglucose 4-epimerase. J. Biol. Chem. 246, 7533–7543.
Zervosen, A., Elling, L., and Kula, M.-R. (1994) Continuous enzymatic synthesis of 2′-Deoxythymidine-5′-(α-D-glucopyranosyl)-diphosphate. Angew. Chem. Int. Ed. Engl. 33, 571–572.
Bergmeyer, H. U. (1974) Adenosine 5′-diphosphoglucose. Methods Enzymatic Analysis 7, 496–502.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1999 Humana Press Inc., Totowa, NJ
About this protocol
Cite this protocol
Zervosen, A., Elling, L. (1999). Application of Sucrose Synthase in the Synthesis of Nucleotide Sugars and Saccharides. In: Bucke, C. (eds) Carbohydrate Biotechnology Protocols. Methods in Biotechnology™, vol 10. Humana Press. https://doi.org/10.1007/978-1-59259-261-6_19
Download citation
DOI: https://doi.org/10.1007/978-1-59259-261-6_19
Publisher Name: Humana Press
Print ISBN: 978-0-89603-563-8
Online ISBN: 978-1-59259-261-6
eBook Packages: Springer Protocols