[60]Fullerenyl amino acids and peptides: a review of their synthesis and applications

Abstract

This review reports on the latest progress in the synthesis of fullerenyl amino acids and related derivatives, and categorises the molecules into functional types for different uses: these include directly attached fullerenyl amino acids, fullerenyl N-and C-capping amino acids, and those amino acids in which the [60]fullerene group is attached to the amino acid side chain. These first and last mentioned derivatives have the potential to be incorporated into non-terminal positions of peptides. The applications of these substrates, by integration into different biological and materials chemistry programs, are also highlighted. This review reports on the latest progress in the synthesis of fullerenyl amino acids and related derivatives, and categorises the molecules into functional types for different uses: these include directly attached fullerenyl amino acids, fullerenyl N-and C-capping amino acids, and those amino acids in which the [60]fullerene group is attached to the amino acid side chain. These first and last mentioned derivatives have the potential to be incorporated into non-terminal positions of peptides. Disciplines Medicine and Health Sciences | Social and Behavioral SciencesThe applications of these substrates, by integration into different biological and materials chemistry programs, are also highlighted.

Fullerenes in biology and medicine

“…101 studied the rate constants of highly hydroxylated fullerene C 60 (OH) 36 interacting with hydroxyl radicals ( ● OH) and hydrated electrons. The rate constant for the reaction of C 60 (OH) 36 with ● OH was 2.0×10 9 dm 3 mol -1 s -1 , which was similar to that for C 60 (OH) 18 ), 4.5×10 -8 dm 3 mol -1 s -1 . 102 These results showed that the decreased number of π bonds, due to the larger number of OH groups attached to the fullerene, did not significantly affect the rate constant for the reaction with hydroxyl radicals.…”

Individual (f,tA)‐ and (f,tC)‐Fullerene‐Based Nickel(II) Glycinates: Protected Chiral Amino Acids Directly Linked to a Chiral π‐Electron System

“…Currently, 20 years after the pioneering work of Prato and co‐workers on stereoselective preparation of diasteroisomeric fullero‐pyrrolidines, still only few examples of stereoselective functionalization of fullerenes are known . Mainly, these are five‐membered carbo‐ and heterocyclic fullerene derivatives with chiral elements located exclusively in the addends or in the side chain of the amino acid . The first examples of an amino acid directly linked to a fullerene obtained by Prato and co‐workers were of the fullero‐pyrrolidine type .…”

[60]Fullerene-peptides: bio-nano conjugates with structural and chemical diversity

“…Following this report, a wide range of alternative linkage groups have been reported as being equally effective in facilitating the attachment of a preformed peptide [24][25][26][27][28][29][30] . Much of this work has been subject to recent reviews [17][18][19][20] , and a selection of the [60]fullerene derivatives used are also shown in Figure 3. One important route that was demonstrated with the immunomodulating peptide tuftsin (Thr-Lys-Pro-Arg) allowed for the covalent conjugate to be formed via either reaction with the amine or carboxylic acid termini ( Figure 4), which provides a flexibility to attach further substituents.…”

“…The topic of [60]fullerene-peptide derivatives has been reviewed [17][18][19][20] ; however, recent results have shown the versatility of both synthetic methods and applications, and suggest that a fresh view is warranted.…”