Controlling the Helicity of Hydroxyquinoline Metal Complexes Based on a Macrocyclic Peptide Scaffold

Ziegler, Eva; Haberhauer, Gebhard

doi:10.1002/ejoc.200900250

Cited by 8 publications

(7 citation statements)

References 44 publications

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“…17). 47 Presuming that the transition dipole moment of quinolinolate chelates lies in the ligand plane and is oriented roughly parallel to the vector connecting the N and O donor atoms, the CD spectra clearly imply that the absolute configuration of these complexes is K. The reported computational results are in accord with this analysis.…”

Section: Exciton Coupling In the CD Spectra Of Mononuclear Complexessupporting

confidence: 61%

Exciton coupling in coordination compounds

2011

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This Perspective reviews the impact of exciton coupling on the spectroscopic properties of coordination compounds. Exciton coupling features arise in electronic absorption and circular dichroism spectra when chromophores are brought into close spatial proximity, for example by coordination to a metal centre. The analysis of these features can reveal much information such as the geometry of a complex and its absolute configuration. The extension of the exciton coupling model to polynuclear metallosupramolecular arrays is discussed.

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Section: Exciton Coupling In the CD Spectra Of Mononuclear Complexessupporting

confidence: 61%

Exciton coupling in coordination compounds

2011

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“…The ligand design is based upon a two-synthon approach (Scheme ) by performing a (CuAAC) click reaction with the azide-functionalized hydroxyquinoline complexation unit S1 and an aromatic dialkyne bearing, e.g., a suitable solubilizing group S2 for the formation of the ligand backbone. The azide S1 is obtained in five steps, with the first four steps being well reported in the literature, which yield Boc-protected 3-(bromomethyl)-quinolin-8-ol ( 5 ). , Dialkyne S2 bearing a diphenylamide solubility group was synthesized from commercially available 3,5-dibromobenzoic acid ( 6 ) in four steps via an acid chloride-mediated amide synthesis and Sonogashira reaction. Additionally, we used commercially available 1,3-diethynylbenzene as a replacement for dialkyne S2 to reduce the solubility of the final host for crystallization purposes.…”

Section: Results and Discussionmentioning

confidence: 99%

“…The azide S1 is obtained in five steps, with the first four steps being well reported in the literature, which yield Boc-protected 3-(bromomethyl)-quinolin-8-ol (5). 69,70 Dialkyne S2 bearing a diphenylamide solubility group was synthesized from commercially available 3,5-dibromobenzoic acid (6) in four steps via an acid chloride-mediated amide synthesis and Sonogashira reaction. Additionally, we used commercially available 1,3diethynylbenzene as a replacement for dialkyne S2 to reduce the solubility of the final host for crystallization purposes.…”

Section: ■ Introductionmentioning

confidence: 99%

A Charge-Neutral Self-Assembled L₂Zn₂ Helicate as Bench-Stable Receptor for Anion Recognition at Nanomolar Concentration

2022

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The field of anion recognition chemistry is dominated by two fundamental approaches to design receptors. One relies on the formation of covalent bonds resulting in organic and often neutral host species, while the other one utilizes metal-driven self-assembly for the formation of charged receptors with well-defined nanocavities. Yet, the combination of their individual advantages in the form of charge-neutral metal-assembled bench-stable anion receptors is severely lacking. Herein, we present a fluorescent and uncharged double-stranded hydroxyquinoline-based zinc(II) helicate with the ability to bind environmentally relevant dicarboxylate anions with high fidelity in dimethyl sulfoxide (DMSO) at nanomolar concentrations. These dianions are pinned between zinc(II) centers with binding constants up to 145 000 000 M −1 . The presented investigation exemplifies a pathway to bridge the two design approaches and combine their strength in one structural motif as an efficient anion receptor.

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“…Tripodal ligands 35-36 with three 9hydroxyquinoline binding arms form octahedral mononuclear complexes with various trivalent metal ions (Scheme 23.11) [43,44]. Tripodal ligands 35-36 with three 9hydroxyquinoline binding arms form octahedral mononuclear complexes with various trivalent metal ions (Scheme 23.11) [43,44].…”

Section: Applications Of Lissoclinum-related Macrocyclic Peptides As mentioning

confidence: 99%

Structures of Azole‐Containing Macrocyclic Peptides

Haberhauer

2011

Modeling of Molecular Properties

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The substantial subclass of known organic heterocyclic compounds containing a fivemembered aromatic ring with at least one nitrogen atom is termed as the azoles [1]. This parent class of heterocycles, together with its reduced analogs azolines and azolidines, can be found in various important biomolecules, such as amino acid building blocks (proline, histidine, tryptophan) of many proteins (myoglobin, carboxypeptidase A, azurin, etc.), natural tetrapyrrolic pigments (hemoglobin, chlorophyll), vitamins (thiamine, cobalamin, biotin), and nucleobases (adenine, guanine) [2]. In addition, many secondary metabolites of living organisms, many alkaloids contain five-membered aza-heterocycles and demonstrate a wide range of physiological properties [3]. The importance of azole-related synthetic organic compounds is also obvious in everyday life, covering various fields of application in human civilization and economy. For example, synthetic pyrrole and imidazole derivatives are among the most commonly prescribed and top-selling active pharmaceutical ingredients (APIs) (Scheme 23.1) [4], while some of the most profitable crop-protection chemicals also incorporate five-membered aza-, oxaza-, and thiazaheterocycles (Scheme 23.2) [5]. Several industrial food additives contain pyrazole (E102, E107) and imidazole (E234, E239, E626-629, E630-633), as well as thiazole (E239, E700) and isothiazole (E954) substructures [6].Apart from the life sciences and related chemical technologies, other branches of the chemical industry produce and utilize azole derivatives of high structural diversity. For example, quaternary imidazolium and pyrrolium salts with ionic liquid properties excel as reaction mediums, extraction and processing solvents, heat storage and transfer fluids, low-temperature electrolytes, lubricants, or seals [7]. Modeling of Molecular Properties, First Edition. Edited by Peter Comba. Scheme 23.2 Chemical structure of some well-known azole-containing pesticides. 366j 23 Structures of Azole-Containing Macrocyclic Peptides 7 Patellamide D Scheme 23.3 Structural formulae of selected cyclohexa-, cyclohepta-, and cyclooctapeptide Lissoclinum alkaloids. 23.2 Azole-Containing Macrocyclic Peptides in Nature j367 Figure 23.2 Optimized structures of lissoclinamide 7 (3, left) and cis,cis-ceratospongamide (4), using B3LYP/6-31G Ã . 372j 23 Structures of Azole-Containing Macrocyclic Peptides

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Controlling the Helicity of Hydroxyquinoline Metal Complexes Based on a Macrocyclic Peptide Scaffold

Abstract: A straightforward synthesis of a C 3 -symmetric imidazolecontaining macrocyclic peptide with three hydroxyquinoline side arms is presented.

Cited by 8 publications

References 44 publications

Exciton coupling in coordination compounds

Exciton coupling in coordination compounds

A Charge-Neutral Self-Assembled L₂Zn₂ Helicate as Bench-Stable Receptor for Anion Recognition at Nanomolar Concentration

Structures of Azole‐Containing Macrocyclic Peptides

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Controlling the Helicity of Hydroxyquinoline Metal Complexes Based on a Macrocyclic Peptide Scaffold

Abstract: A straightforward synthesis of a C 3 -symmetric imidazolecontaining macrocyclic peptide with three hydroxyquinoline side arms is presented.

Cited by 8 publications

References 44 publications

Exciton coupling in coordination compounds

Exciton coupling in coordination compounds

A Charge-Neutral Self-Assembled L2Zn2 Helicate as Bench-Stable Receptor for Anion Recognition at Nanomolar Concentration

Structures of Azole‐Containing Macrocyclic Peptides

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A Charge-Neutral Self-Assembled L₂Zn₂ Helicate as Bench-Stable Receptor for Anion Recognition at Nanomolar Concentration