Synthesis and characterization of water-soluble C₆₀–peptide conjugates

• Yue Ma,
• Lorenzo Persi and
• Yoko Yamakoshi

Beilstein J. Org. Chem. 2024, 20, 777–786, doi:10.3762/bjoc.20.71

• of hydrophilic oligopeptide anchors (oligo-Lys, oligo-Glu, and oligo-Arg) were synthesized. A previously reported Prato reaction adduct of a biscarboxylic acid-substituted C60 derivative was subjected to a solid phase synthesis for amide formation with N-terminal amines of peptides on resin to

• inhibition [34]. For the covalent functionalization, we have previously developed a versatile and convenient biscarboxylic acid-substituted C60 derivative (3, Figure 1) [35], which was prepared via the Prato reaction [36]. We used this derivative 3 as a starting material and synthesized a series of water

• on resin, a GABA residue was attached to the N-terminus of the peptide in order to provide a less-hindered primary amine, enabling an efficient amide conjugation reaction with biscarboxylic acid-substituted C60 derivative 3. Compound 3 was prepared by Prato reaction of C60 and an N-glycine derivative

Site-selective covalent functionalization at interior carbon atoms and on the rim of circumtrindene, a C₃₆H₁₂ open geodesic polyarene

• Hee Yeon Cho,
• Ronald B. M. Ansems and
• Lawrence T. Scott

Beilstein J. Org. Chem. 2014, 10, 956–968, doi:10.3762/bjoc.10.94

• ; polycyclic aromatic hydrocarbon; Prato reaction; Introduction Investigations into the structures and properties of geodesic polyarenes began with the synthesis of corannulene (1, C20H10) in 1966 [1][2] and were greatly stimulated by the discovery of buckminsterfullerene (2, C60) in 1985 (Figure 1) [3

• [29][30] and the Prato reaction [31][32] are illustrated in Scheme 1. The Bingel–Hirsch reaction affords a cyclopropanated fullerene 7, and the Prato reaction gives a [3 + 2] cycloaddition adduct 8. Concurrent with the development of covalent functionalization, numerous noncovalent functionalization

• side electronically more favorable for a nucleophilic attack. Prato reaction Cycloadditions to the π-system constitute another major family of fullerene reactions. In particular, 1,3-dipolar reagents readily add to the 6:6-bond of fullerene C60, which acts as a good dipolarophile. Among such [3 + 2

Tuning the interactions between electron spins in fullerene-based triad systems

• Maria A. Lebedeva,
• Thomas W. Chamberlain,
• E. Stephen Davies,
• Bradley E. Thomas,
• Martin Schröder and
• Andrei N. Khlobystov

Beilstein J. Org. Chem. 2014, 10, 332–343, doi:10.3762/bjoc.10.31

• the nature of the fullerene cages resulting in the preparation of six fullerene–linker–fullerene (triad) compounds (Figure 1). The fullerenes were functionalised via Prato reaction chemistry forming a pyrrolidine ring across the [6.6] bond of the cage [21]. The resulting pyrrolidine functionalised

• the assignment of redox processes in the triad species. The triads 1–3 were synthesised in five steps by functionalisation of each fullerene cage using the Prato reaction, addition of the terephthalate spacer to the fulleropyrrolidine unit and subsequent coupling of two fullerene moieties [20]. The