Synthesis of a <i>C</i><sub>3</sub>‐Symmetric Furyl‐Cyclopeptide Platform with Anion Recognition Properties

Molina, Lidia; Moreno‐Clavijo, Elena; Vargas, Ângelo; Carmona, Ana T.; Robina, Inmaculada

doi:10.1002/ejoc.201000219

Cited by 9 publications

(6 citation statements)

References 69 publications

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“…Cyclopeptide-based receptors have also been described featuring only abiotic amino acids along the ring. Somewhat related to the compounds described in the previous section are the furan-derived cyclopeptides 49a-d described by Chakraborty and coworkers [175,176] and the structurally related analog 50 developed in the Robina group (Figure 19a) [177]. According to force-field calculations, 49a preferentially adopts an almost planar C 3 symmetric conformation with converging NH groups.…”

Section: Cyclic Peptides Not Containing α-Amino Acid-derived Subunitsmentioning

confidence: 90%

Synthetic Receptors Based on Abiotic Cyclo(pseudo)peptides

Kubik

2022

Molecules

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Work on the use of cyclic peptides or pseudopeptides as synthetic receptors started even before the field of supramolecular chemistry was firmly established. Research initially focused on the development of synthetic ionophores and involved the use of macrocycles with a repeating sequence of subunits along the ring to facilitate the correlation between structure, conformation, and binding properties. Later, nonnatural amino acids as building blocks were also considered. With growing research in this area, cyclopeptides and related macrocycles developed into an important and structurally diverse receptor family. This review provides an overview of these developments, starting from the early years. The presented systems are classified according to characteristic structural elements present along the ring. Wherever possible, structural aspects are correlated with binding properties to illustrate how natural or nonnatural amino acids affect binding properties.

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Section: Cyclic Peptides Not Containing α-Amino Acid-derived Subunitsmentioning

confidence: 90%

Synthetic Receptors Based on Abiotic Cyclo(pseudo)peptides

Kubik

2022

Molecules

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“…64 Another furyl cyclopeptide 37 has recently been developed by Robina and co-workers, the ability of which to bind cyanide, acetate and chloride anions was determined by 1 H NMR titrations in CD 3 CN. 65 This ''bowl-like'' structure was found to form 1 : 1 anion : receptor complexes with cyanide, acetate and chloride anions where chloride was found to have the tightest association with receptor 37 exhibiting a binding constant of K = 1.63 Â 10 4 M À1 .…”

Section: Backbone Modified Cyclic Peptidesmentioning

confidence: 99%

Anion recognition by cyclic peptides

Elmes

Jolliffe

2015

Chem. Commun.

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Anion binding selectivity can often be controlled by judicious arrangement of recognition moieties around an anion of interest. Indeed, nature takes advantage of large peptides/proteins to provide highly efficient and selective anion receptors using a small number of amino acid building blocks placed in a precise arrangement. Cyclic peptides are ideal synthetic scaffolds to position binding residues in a similarly preorganised manner as their synthetic versatility and rigidified structure allows precise control over their size and shape. This review summarises the recent use of such cyclic peptide scaffolds as receptors for various anionic species.

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“…The only example of a macrocycle containing a 2,4disubstituted furan moiety is compound 251 (Scheme 50). 114 The building block for its synthesis was compound 252, which was prepared as follows. Condensation of benzyl acetoacetate with D-xylose led to the formation of polyol 253.…”

Section: Incorporation Of Furan By Positions 2 Andmentioning

confidence: 99%

Heteroaryl Rings in Peptide Macrocycles

2019

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This Review is devoted to the chemistry of macrocyclic peptides having heterocyclic fragments in their structure. These motifs are present in many natural products and synthetic macrocycles designed against a particular biochemical target. Thiazole and oxazole are particularly common constituents of naturally occurring macrocyclic peptide molecules. This frequency of occurrence is because the thiazole and oxazole rings originate from cysteine, serine, and threonine residues. Whereas other heteroaryl groups are found less frequently, they offer many insightful lessons that range from conformational control to receptor/ligand interactions. Many options to develop new and improved technologies to prepare natural products have appeared in recent years, and the synthetic community has been pursuing synthetic macrocycles that have no precedent in nature. This Review attempts to summarize progress in this area.

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Synthesis of a C₃‐Symmetric Furyl‐Cyclopeptide Platform with Anion Recognition Properties

Abstract: A new furyl amino acid derivative was trimerized to give a linear peptide and finally was cyclized. The newly generated cyclopeptide was subjected to a conformational study in order to be considered as a C 3 -symmetric platform for the ratio-

Cited by 9 publications

References 69 publications

Synthetic Receptors Based on Abiotic Cyclo(pseudo)peptides

Synthetic Receptors Based on Abiotic Cyclo(pseudo)peptides

Anion recognition by cyclic peptides

Heteroaryl Rings in Peptide Macrocycles

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Synthesis of a C3‐Symmetric Furyl‐Cyclopeptide Platform with Anion Recognition Properties

Abstract: A new furyl amino acid derivative was trimerized to give a linear peptide and finally was cyclized. The newly generated cyclopeptide was subjected to a conformational study in order to be considered as a C 3 -symmetric platform for the ratio-

Cited by 9 publications

References 69 publications

Synthetic Receptors Based on Abiotic Cyclo(pseudo)peptides

Synthetic Receptors Based on Abiotic Cyclo(pseudo)peptides

Anion recognition by cyclic peptides

Heteroaryl Rings in Peptide Macrocycles

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Product

Resources

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Synthesis of a C₃‐Symmetric Furyl‐Cyclopeptide Platform with Anion Recognition Properties