Organic Chemistry, Short Talk
OC-013

Glucose-derived selective receptors of amino acids in aqueous environments.

B. Lewandowski1, M. M. Most2*, L. B. Boll1*, P. Gödtel2*, Z. L. Pianowski2*
1Laboratory of Organic Chemistry ETH Zürich, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland, 2Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Kaiserstrasse 12, 76131 Karlsruhe, Germany

Amino acids play key roles in numerous biological processes.[1] They also found applications in asymmetric synthesis and catalysis,[2] chemical biology[3] and materials science.[4] Selective binding of amino acids, in particular in water, is therefore important for diagnostic, medicinal and technological purposes.[5] However, it is also challenging since it requires a combination of hydrophobic and polar interactions for binding.[6] Recently, we reported glucose-derived crown and benzocrown ethers capable of enantioselective binding of amino acid esters with hydrophobic and aromatic side chains in water.[7,8] Herein, we will present a glucose naphtho crown ether (Fig. 1a) which binds tryptophan selectively over other amino acids in aqueous media.[9] This receptor is also capable of binding to tryptophan residues within peptides. The naphthalene unit in the receptor allows to monitor the binding process with fluorescence spectroscopy.

Furthermore, we will present glucose-based photoswitchable receptors of amino-acid esters and biogenic amines (Fig. 1b).[10] The tetrafluoroazobenzene unit in the receptors structure allows to control their binding affinity to dicationic guests, such as lysine, arginine and ornithine esters, in water and PBS buffer, using light. The Z isomers of the receptors display 3-4 x higher affinities to the guests than the E isomers.

[1] Amino Acids: Biochemistry and Nutrition (Ed.: G. Wu), CRC Press, Boca Raton, 2010.

[2] S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471–5569.

[3] Z. Cheng, E. Kuru, A. Sachdeva, N. Wendrell, Nature Rev. Chem. 2020, 4, 275–290.

[4] D. Chakraborty, E. Gazit, Chem. Nano. Mat. 2018, 4, 730–740.

[5] D. Maity, C. Schmuck "Synthetic receptors for amino acids and peptides” in Monographs in Supramolecular Chemistry (Ed.: B. Smith) The Royal Society of Chemistry, 2015, pp. 326–368.

[6] H. P. Ferguson Johns, E. E. Harrison, K. J. Stingley, M. L. Waters, Chem. Eur. J. 2021, 27, 6620–6644.

[7] P. Dominique, M. Schnurr, B. Lewandowski, Chem. Commun. 2021, 57, 3476–3479.

[8] M. H. Chak, M. Schnurr, B. Lewandowski, Eur. J. Org. Chem. 2023, e202300305.

[9] G. Gallo, B. Lewandowski, Beilstein J. Org. Chem. 2025, 21, 541–546.

[10] M. M. Most, L. B. Boll, P. Gödtel, Z. L. Pianowski, B. Lewandowski, Commun. Chem. 2025, 8, 50.