Supramolecular Chemistry of Modified Amino Acids and Short Peptides
Pp. 43-107 (65)
Joanna Bojarska, Krzysztof Kaczmarek, Janusz Zabrocki and Wojciech M. Wolf
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
Amino acids, Cyclic peptides, Non-covalent interactions, Organic
synthesis, Short peptides, Supramolecular architecture, Supramolecular assembly,
Supramolecular synthesis, Supermolecule, Synthon concept.
Department of Chemistry, Institute of General and Ecological Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Lodz, Poland.