Differentiation of enantiomers remains one of the most attractive and important research areas due to its impact on pharmaceutical, chemical, biotechnology, and food industries. The development of fast and reliable chiral sensors remains a challenge to achieve on-line analysis of enantiomers [1].

In our studies we found that structures formed by self organization of N-lipidated amino acids [2] and peptides [3] immobilized in a regular pattern on a cellulose surface  via  triazine  linker  are  able  to  recognize  the  shape  and  properties  of  ligands,  and  then selectively bind guest molecules matching the requirements of the binding pocket. Our previous studies documented that the process of binding guest molecules is reversible and competitive.

Due to the conformational  flexibility  of  both  interacting  partners,  the  relative  direction  of  the  functional groups  of  a  ligand  as  well  as  that  of  the  binding  pockets  could  be  readjusted  to  the  most energetically favored orientation of both counterparts. Therefore, it has been expected that ligand binding profile to the receptor pocket formed from chiral        N-lipidated peptides immobilized on chiral solid support (cellulose) will be depended on the configuration of the ligand. To check the versatility of artificial receptors formed by self-organization of N-lipidated amino acids and peptides immobilized on cellulose as a stereosectors it has been compared binding profile for both enantiomers of Aib-Ala. It has been found that binding pockets of artificial receptors are able to differentiate configuration of docked molecules.

Acknowledgement:

This work was supported by Ministry of Science and Education Poland N N 405 669540.

References:

[1] Manoli, K.; Magliulo, M.; Torsi, L. Top Curr Chem. 2013, 341, 133.

[2] Fraczyk, J.; Kaminski, Z. J. J. Comb. Chem. 2008, 10, 934.

[3] a) Fraczyk, J.; Malawska, B,; Kaminski, Z. J. J. Comb. Chem. 2009, 11, 446; b) Fraczyk,  J.;  Kolesinska,  B.;  Czarnecka,  A.;  Malawska,  B.;  Wieckowska,  A.;  Bajda,  M.; Kaminski, Z. J. QSAR & Comb. Sci. 2009, 28, 728.

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