Complexation of arginine with a cyclopeptide in polar solvents and water

Bitta, Joachim; Kubik, Stefan

doi:10.1016/s1472-7862(02)00073-4

Cited by 8 publications

(2 citation statements)

References 17 publications

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“…Further structural modifications of these cyclopeptides mainly involved the introduction of substituents into the aromatic subunits to induce affinity for carbohydrates [98,99] or amino acids [100], or into the proline rings to mediate sulfate binding [101]. In addition, the replacement of amide groups along the ring by other linking units was also explored.…”

Section: Cyclic Peptides and Pseudopeptides Containing Six-membered A...mentioning

confidence: 99%

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 and Pseudopeptides Containing Six-membered A...mentioning

confidence: 99%

Synthetic Receptors Based on Abiotic Cyclo(pseudo)peptides

Kubik

2022

Molecules

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“…There are various experimental [6][7][8] and theoretical [9][10][11][12] studies dedicated to examine different aspects of this phenomenon. The cyclic peptides are used as excellent host in host-guest chemistry because they could form inclusion complexes with guest molecules [13][14][15][16][17][18][19][20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric discrimination of leucine enantiomers by nanotubular cyclic peptides: DFT and ONIOM calculation of the absorption spectra of guested enantiomers

Shahangi

Chermahini

Farrokhpour

et al. 2016

J Incl Phenom Macrocycl Chem

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In this work, the inclusion complexes of leucine as the guest and a series of cyclic peptides with four to nine alanine as building block (host molecules) were investigated by M062X/6-31 ? G (d) level of theory. The calculations predicted the stability of the enantiomers in the cavity of cyclic peptides and the possibility of distinction between the enantiomers for the used level of theory. The results indicated that the most stable aggregate is formed between CyclAla9 and R and S-leucine enantiomers and CyclALA4 have the least interaction with R and S-leucine enantiomers. Geometrical changes of leucine due to complexation and hydrogen bonding were considered. The NBO calculations for analyzing the nature of the intermolecular hydrogen bonds were performed. In another part of this work, the UV absorption spectra of complexes of R, and S-leucine with CyclAla9 calculated using ONIOM method in the gas phase and it was showed that the UV absorption spectroscopy could be used as a chirality discriminator tool in recognition of enantiomers in the gas phase.

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Cyclopeptide Derived Synthetic Receptors

Kubik

2010

Artificial Receptors for Chemical Sensors

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Complexation of arginine with a cyclopeptide in polar solvents and water

Cited by 8 publications

References 17 publications

Synthetic Receptors Based on Abiotic Cyclo(pseudo)peptides

Synthetic Receptors Based on Abiotic Cyclo(pseudo)peptides

Enantiomeric discrimination of leucine enantiomers by nanotubular cyclic peptides: DFT and ONIOM calculation of the absorption spectra of guested enantiomers

Cyclopeptide Derived Synthetic Receptors

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