Synthesis of novel cyclopeptides containing heterocyclic skeletons

Abstract

This review highlights different approaches for the synthesis of cyclopeptides containing heterocyclic skeletons such as triazole, imidazole, tetrazole, oxazole and thiazole.

Grafting Bis(heteroaryl) Motifs into Ring Structures

“…This connectivity could potentially confer distinct conformational properties. Heterocyclic grafts in peptide macrocycles are known to reduce conformational flexibility through the introduction of an sp 2 ‐rich segment within the macrocyclic backbone , . In the case of cyclo‐GFGAH, the 1 H NMR spectrum hydrogen‐bonding pattern of the N τ ‐regioisomer was compared with a homedetic analog by variable temperature 1 H NMR (Figure A ).…”

Recent Progress in Solid‐Phase Total Synthesis of Naturally Occurring Small Peptides

“…[16][17][18][19][20][21][22] Accompanying these developments of solid-phase organic synthesis, some synthetic methodologies primarily utilized in the solution phase successfully transferred onto the solid phase, which is in turn to promote the development of solid-phase peptide synthesis. [23][24][25][26][27] Although some reviews related to the SPPS have mentioned some cases of natural peptides in recent years, they are mainly focused on the topics of the green and sustainable SPPS, [28][29][30] synthesis of one specified category of peptides, [31] or talking about certain strategies (Fmoc SPPS, [32] peptide ligation, [33] transition-metal catalysis, [34] etc.). Few of them are specially focused on the naturally occurring small peptide synthesis.…”

“…In addition, the solid‐phase synthesis of small organic molecules has been rapidly developed since 1990s [16–22] . Accompanying these developments of solid‐phase organic synthesis, some synthetic methodologies primarily utilized in the solution phase successfully transferred onto the solid phase, which is in turn to promote the development of solid‐phase peptide synthesis [23–27] …”

Impact of the Histidine-Triazole and Tryptophan-Pyrene Exchange in the WHW Peptide: Cu(II) Binding, DNA/RNA Interactions and Bioactivity

“…Namely, 1,2,3-triazoles possesses two nitrogen atoms capable of coordinating metals and represents a good ligand moiety for transition metal complexes [23,24]. They are often used in peptides to mimic a trans-amide bond [25][26][27] and as an attractive bridging group to link two pharmacophores [28,29]. More importantly, the introduction of 1,2,3-triazoles by copper(I)-catalysed 'click' chemistry (CuAAC) is often used for the introduction of various molecular tools, like fluorophores or similar.…”