Synthetic carbohydrate-based materials

Dr. Martina Delbianco, Max Planck Institute of Colloids and Interfaces, Postdam-Golm, Germany

Natural biopolymers have inspired the development of synthetic analogues capable of adopting defined conformations and forming programmable three-dimensional architectures. These compounds are mainly based on peptides and nucleic acids, that are well understood at the molecular level. In contrast, the complexity of carbohydrate synthesis and structural analysis have prevented access to synthetic carbohydrates capable of adopting defined geometries. In the Delbianco group, we prepare well-defined oligosaccharides to understand how the primary sequence affects the carbohydrate conformation.¹ With multiple analytical techniques, we study the conformation of single carbohydrate chains² and explore how several carbohydrate molecules aggregate to form a material³. Building on this fundamental knowledge, we present the rational design and synthesis of a glycan adopting a stable secondary structure,⁴ challenging the common belief that glycans are not capable of folding due to their flexibility. The ability to control the conformation of glycans could lead to the generation of programmable 3-D architectures, with applications in catalysis and nanotechnology.

References:
1. Y. Yu, T. Tyrikos-Ergas, Y. Zhu, G. Fittolani, V. Bordoni, A. Singhal, R. J. Fair, A. Grafmüller, P. H. Seeberger, M. Delbianco, Angew. Chem., Int. Ed. 2019, 58, 1433-7851
2. X. Wu, M. Delbianco, K. Anggara, T. Michnowicz, A. Pardo-Vargas, P. Bharate, S. Sen, M. Pristl, S. Rauschenbach, U. Schlickum, S. Abb, P. H. Seeberger, K. Kern, Nature 2020, 582, 375-378.
3. G. Fittolani, D. Vargová, P. H. Seeberger, Y. Ogawa, M. Delbianco, J. Am. Chem. Soc. 2022, 144, 12469-12475.
4. G. Fittolani, T. Tyrikos-Ergas, Y. Yu, N. Yadav, P.H. Seeberger, J. Jiménez-Barbero, M. Delbianco, Synthesis of a glycan hairpin, Nat. Chem., 2023, 15, 1461