Binding of amino acids in water to a highly electron-rich aromatic cavity of pyrogallol or resorcinol cyclic tetramer as π-base

Kobayashi, Kenji; Tominaga, Makio; Asakawa, Yuji; Aoyama, Yasuhiro

doi:10.1016/s0040-4039(00)60692-5

Cited by 33 publications

(9 citation statements)

References 10 publications

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“…Complex formation in solution of calixarene-based hosts with various substrates (nonpolar molecules, 204 carbohydrates, 205 amino acids, 206 alcohols or ketones, 207 neutral ditopic molecules including amides, 208 quaternary ammonium ions, etc 209 ) has been reported by many workers. In every case the nonpolar CH group was found to contribute in the binding.…”

Section: Calixarene Complexesmentioning

confidence: 99%

CH/? hydrogen bonds in crystals

Nishio¹

2004

CrystEngComm

1,389

781

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The nature and characteristics of the CH/p interaction are discussed by comparison with other weak molecular forces such as the CH/O and OH/p interaction. The CH/p interaction is a kind of hydrogen bond operating between a soft acid CH and a soft base p-system (double and triple bonds, C 6 and C 5 aromatic rings, heteroaromatics, convex surfaces of fullerenes and nanotubes). The consequences of CH/p hydrogen bonds in supramolecular chemistry are reviewed on grounds of recent crystallographic findings and database analyses. The topics include intramolecular interactions, crystal packing (organic and organometallic compounds), host/ guest complexes (cavity-type inclusion compounds of cyclodextrins and synthetic macrocyclic hosts such as calixarenes, catenanes, rotaxanes and pseudorotaxanes), lattice-inclusion type clathrates (including liquid crystals, porphyrin derivatives, cyclopentadienyl compounds and C 60 fullerenes), enantioselective clathrate formation, catalytic enantioface discriminating reactions and solid-state photoreaction. The implications of the CH/p concept for crystal engineering and drug design are evident.

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Section: Calixarene Complexesmentioning

confidence: 99%

CH/? hydrogen bonds in crystals

Nishio¹

2004

CrystEngComm

1,389

781

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“…Derivatives of calix[ n ]arenes such as p -sulphonate or methoxycarboxylic derivatives form stable complexes with Zn 2+ , Cu 2+ , Ni 2+ under neutral or alkaline conditions [ 226 , 227 , 228 ]. Water soluble resorcin[4]arene derivatives are able to form complexes, not only with the metal ions, but also with amino acids, sugars, and nucleosides [ 229 , 230 , 231 ]. It was demonstrated that p -sulfonatocalix[4,6,8]arene and C -nonylresorcin[4]arene possess antimicrobial activity against fungal and bacterial microorganisms [ 232 ].…”

Section: Influence Of Growth Conditions On Microalgal Resistance Tmentioning

confidence: 99%

Effect of Metals, Metalloids and Metallic Nanoparticles on Microalgae Growth and Industrial Product Biosynthesis: A Review

Miazek

Iwanek

Remacle

et al. 2015

IJMS

212

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Microalgae are a source of numerous compounds that can be used in many branches of industry. Synthesis of such compounds in microalgal cells can be amplified under stress conditions. Exposure to various metals can be one of methods applied to induce cell stress and synthesis of target products in microalgae cultures. In this review, the potential of producing diverse biocompounds (pigments, lipids, exopolymers, peptides, phytohormones, arsenoorganics, nanoparticles) from microalgae cultures upon exposure to various metals, is evaluated. Additionally, different methods to alter microalgae response towards metals and metal stress are described. Finally, possibilities to sustain high growth rates and productivity of microalgal cultures in the presence of metals are discussed.

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“…The hosts include many of the most familiar organic receptors, some of which required special substituents to make them water-soluble: resorcinols, [13] resorcinarenes, [14] cyclophanes, [15] azacyclophanes, [16] ammonium cyclophanes, [17] crown ethers and their nitrogen analogues (macrocyclic polyamines), [18] calixarenes, [19] the cyclophanes of Dougherty and co-workers, [20] a macrocyclic derivative of Tröger's base, [21] flavinophanes, [22] metal-free porphyrins, [23] cyclotetrachromotropylene, [24] the aromatic hosts of Lehn and coworkers, [25] hexapus, [26] and cucurbituril [27] (Figure 6). The K a values are mostly within the range of 1 to 10 7 m À1 (see Figure 5).…”

Section: Synthetic Hostsmentioning

confidence: 99%

“…Examples of non-cyclodextrin water-soluble hosts for organic molecules. [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27] Figure 7. Plot of DH versus DS for non-cyclodextrin organic hostguest complexes in aqueous solution; [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27] linear regression gives DH = 310.7(AE 33.2) DSÀ3.3(AE 0.4).…”

Section: Synthetic Hostsmentioning

confidence: 99%

Binding Affinities of Host–Guest, Protein–Ligand, and Protein–Transition‐State Complexes

et al. 2003

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The affinities of hosts—ranging from small synthetic cavitands to large proteins—for organic molecules are well documented. The average association constants for the binding of organic molecules by cyclodextrins, synthetic hosts, and albumins in water, as well as of catalytic antibodies or enzymes for substrates are 103.5±2.5 M−1. Binding affinities are elevated to 108±2 M−1 for the complexation of transition states and biological antigens by antibodies or inhibitors by enzymes, and to 1016±4 M−1 for transition states with enzymes. The origins of the distributions of association constants observed for the broad range of host–guest systems are explored in this Review, and typical approaches to compute and analyze host–guest binding in solution are discussed. In many classes of complexes a rough correlation is found between the binding affinity and the surface area that is buried upon complexation. Enzymes transcend this effect and achieve transition‐state binding much greater than is expected from the surface areas.

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Binding of amino acids in water to a highly electron-rich aromatic cavity of pyrogallol or resorcinol cyclic tetramer as π-base

Cited by 33 publications

References 10 publications

CH/? hydrogen bonds in crystals

CH/? hydrogen bonds in crystals

Effect of Metals, Metalloids and Metallic Nanoparticles on Microalgae Growth and Industrial Product Biosynthesis: A Review

Binding Affinities of Host–Guest, Protein–Ligand, and Protein–Transition‐State Complexes

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