Synthesis and structure of lower rim C-linked tetra-N-tosyl peptidocalix[4]arenes

Sdira, Sofiane Ben; Baudry, R.; Félix, C.; Giudicelli, Marie-BéatriceA.; Lamartine, R.

doi:10.1016/j.tetlet.2004.07.078

Cited by 8 publications

(5 citation statements)

References 25 publications

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“…The NMR in CDCl 3 solutions at 300 K and mass spectrometry studies were carried out to disclose the supramolecular interactions involved in the enantioselective recognition of N-tosyl-amino acids (Val, Leu, and Phe). All receptors, 53a-b and 54a-b, formed stable 1 : 1 complexes with amino acids in CDCl 3 with moderate values of binding constants compared with those obtained for anionic guests, [110][111][112] which may be due to the rather weak hydrogen bonding interaction between the host and the guest. Receptors 53b…”

Section: Chiral Recognition Of Amino Acids By Peptido-and Glycocalix[...mentioning

confidence: 82%

“…110 Structurally related with chiral receptors p-tert-butylcalix [4]arenes 1,3-difunctionalized are the chiral p-tert-butylcalix [4]arenes (52a-e) perfunctionalised at the lower rim with amino acid units. 112 The recognition properties of N-tosylated calix [4]arene derivative 52a towards various anions, such as tetrabutylammonium chloride (K ass = 4900 M À1 ), bromide (K ass = 3800 M À1 ), dihydrogenphosphate (K ass = 2300 M À1 ), hydrogen sulfate (K ass = 3700 M À1 ) were investigated by 1 H NMR experiments in CDCl 3 . This receptor forms 1 : 1 complexes in CDCl 3 , confirmed by Job plots with all studied anions.…”

Section: Chiral Recognition Of Amino Acids By Peptido-and Glycocalix[...mentioning

confidence: 99%

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Recognition of amino acids by functionalized calixarenes

et al. 2011

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The calixarenic receptors exhibit remarkable host-guest properties towards biologically relevant guests. Aspects of complex formation reactions between both native and derivatized amino acids, di-and tripeptides with calixarenic (chiral or not) receptors are summarized in this critical review. Thus, the discussions emphasize the parameters that affect the molecular binding selectivity and efficiency of functionalized calix[n]arenes towards these substrates. A brief survey on their application in separation of amino acids is also considered (123 references).

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Section: Chiral Recognition Of Amino Acids By Peptido-and Glycocalix[...mentioning

confidence: 82%

Section: Chiral Recognition Of Amino Acids By Peptido-and Glycocalix[...mentioning

confidence: 99%

Recognition of amino acids by functionalized calixarenes

et al. 2011

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“…From the data shown in Table 1 we can deduce that all hosts had moderate binding constants compared with those obtained from anionic guests, 13,14 which may be due to the rather weak hydrogen bonding interaction between the host and the guest. Nevertheless, these values are in accordance with those described in the literature for neutral guests.…”

Section: Complexation Studiesmentioning

confidence: 95%

“…9h,11,12 In previous studies, we described the synthesis of chiral calix [4]arenes grafted with amino-acid units. 13,14 The binding abilities of these receptors with amino-acid carboxylate derivatives were performed. These studies confirmed the need and the effectiveness of hydrogen bonding and p-p stacking.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective recognition of amino acids by chiral peptido-calix[4]arenes and thiacalix[4]arenes

Bois¹,

Bonnamour²,

Duchamp³

et al. 2009

New J. Chem.

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In order to prepare new molecular hosts able to discriminate enantiomers of amino-acid derivatives, we have synthesized chiral thiacalix[4]arenes. Extensive studies using NMR and mass spectrometry techniques allow us to determine the major supramolecular interactions involved in the recognition process. Moreover, a titration study enables us to determine the binding constant between these new hosts and a series of amino-acid derivatives. Finally, we have also demonstrated that these calixarenes are able to discriminate enantiomers of amino-acid guests.

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“…Sdira et al [63,64] synthesized calix [4]arene-based chiral receptors, amino acid conjugates 56a-56e and compound 57 in a cone conformation, functionalized by α-hydroxyamide groups at the lower rim. Strong complexation of 56a was revealed; it gave rise to 1 : 1 complexes with anions with the following binding constants K ass in CDCl 3 : 4900 (Cl -), 3800 (Br -), 3700 (HSO 4 -), and 2300 l mol -1 (H 2 PO 4 -).…”

Section: Chiral Receptors and Enantio-selective Recognitionmentioning

confidence: 99%