Advances in Organic Synthesis

Volume: 11

Supramolecular Chemistry of Modified Amino Acids and Short Peptides

Author(s): Joanna Bojarska, Krzysztof Kaczmarek, Janusz Zabrocki and Wojciech M. Wolf

Pp: 43-107 (65)

DOI: 10.2174/9781681087474118110004


Supramolecular synthesis is a perfect complementary to molecular synthesis in order to create supramolecular assemblies which would not be available by the use of covalent bonds only. The beauty of this advanced synthesis lies in a spontaneous reaction via noncovalent intercontacts, offering endless possibilities, without outside help. Recently, short peptides have attracted an increasing interest due to their advantages and applications, inter alia supramolecular biofunctional materials, in drug delivery, cancer therapy or immunology. Amino acids, simple building blocks in living systems whose architecture is controlled by a plethora of intermolecular interactions, have a valuable input in understanding highly complex biological systems and processes. Subtle supramolecular intercontacts in precise co-operation just like virtuosos play a symphony of life. So, the design of smart bio-inspired materials should be based on the knowledge of intercontacts at a molecular and higher topological level. Nevertheless, information on this subject is very scarce. This chapter is a brief review focused on supramolecular chemistry of short peptides in relation to laboratory synthesis and more comprehensive reaction mechanisms. It summarizes the latest scientific findings scattered across the world literature, the most perspective ways of synthesis and takes a holistic look at the supramolecular landscape in the context of subtle supramolecular effects via modern both experimental and theoretical methods. Special attention is paid to the supramolecular H-bond synthon concept, which evolves in various research areas in an intriguing manner. Synthon methodology is as important in supramolecular chemistry as the reaction mechanism in traditional synthesis. For the synthetic chemists, synthons involving relevant intercontacts are invaluable in the synthetic strategy of self-assembly. We hope that this publication highlighting an innovative approach will contribute to the development of short peptide-based supramolecular chemistry.

Keywords: Amino acids, Cyclic peptides, Non-covalent interactions, Organic synthesis, Short peptides, Supramolecular architecture, Supramolecular assembly, Supramolecular synthesis, Supermolecule, Synthon concept.

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