Zinc(II) complex of terpyridine-crown macrocycle: A new motif in fluorescence sensing of zwitterionic amino acids

Kwong, Hoi‐Lun; Wong, Wing‐Leung; Lee, Chi‐Sing; Yeung, Chi‐Tung; Teng, Pang-Fei

doi:10.1016/j.inoche.2009.06.013

Cited by 50 publications

(16 citation statements)

References 36 publications

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“…152) has been developed for molecular recognition of zwitterionic amino acids in water/DMF solution with strong binding to S -aspartate ( K ass = 4.5 × 10 4 M −1 ) and R -cysteine ( K ass = 2.5 × 10 4 M −1 ) [676]. The Zn(II)-tpy subunit co-ordinates with the carboxylate group of the zwitterionic amino acids, and functions as a chromophore (λ max = 348 nm) for the fluorescence sensing in aqueous solutions.…”

Section: Reviewmentioning

confidence: 99%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

219

130

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SummaryAmmonium ions are ubiquitous in chemistry and molecular biology. Considerable efforts have been undertaken to develop synthetic receptors for their selective molecular recognition. The type of host compounds for organic ammonium ion binding span a wide range from crown ethers to calixarenes to metal complexes. Typical intermolecular interactions are hydrogen bonds, electrostatic and cation–π interactions, hydrophobic interactions or reversible covalent bond formation. In this review we discuss the different classes of synthetic receptors for organic ammonium ion recognition and illustrate the scope and limitations of each class with selected examples from the recent literature. The molecular recognition of ammonium ions in amino acids is included and the enantioselective binding of chiral ammonium ions by synthetic receptors is also covered. In our conclusion we compare the strengths and weaknesses of the different types of ammonium ion receptors which may help to select the best approach for specific applications.

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Section: Reviewmentioning

confidence: 99%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

219

130

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“…The ammonium group of the zwitterionic AAs can coordinate with [Zn (6)] 2+ because of the crown ether subunit in complex [Zn (6)] 2+ , thus providing a stronger binding affinity toward L-AAs, such as L-aspartate (K = 4.5×10 4 M −1 ) and Lcysteine (Cys) (K = 2.5×10 4 M −1 ), as compared with [Zn (7)] 2+ without crown ether. The binding affinity of [Zn (6)] 2+ with L-AAs is highly associated with the coordinating abilities of the side chain on AAs ( Figure 2) [42]. On the other hand, it is difficult to differentiate L-aspartate from L-Cys.…”

mentioning

confidence: 99%

Fluorescent/luminescent detection of natural amino acids by organometallic systems

Wang

Liu

Tong

et al. 2015

Coordination Chemistry Reviews

123

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Section: Discussionmentioning

confidence: 99%

“…Kwong et al designed terpyridino‐crown ether ( S,S,S,S,S,S )‐ 11 and its Zn 2+ complex ( S,S,S,S,S,S )‐ 12 (Figure ) for fluorescent sensing of amino acids and their derivatives . The complexation processes with the guests could also be followed by absorption spectral changes . Addition of the enantiomers of PhgOMe·Cl (Figure ) to ligand ( S,S,S,S,S,S )‐ 11 in dichloromethane induced quenching of the emission peak at 355 nm, and the simultaneous appearance of a weak band at 430 nm .…”

Section: Discussionmentioning

confidence: 99%

Optically active crown ether‐based fluorescent sensor molecules: A mini‐review

Móczár

Huszthy

2018

Chirality

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This mini‐review focuses on fluorescent optically active crown ethers (polymeric derivatives are not included) reported in the literature (according to our knowledge), of which enantiomeric recognition ability, and in some cases, also inorganic cation complexation properties, were investigated by the sensitive and versatile fluorescence spectroscopy. These crown ether‐based chemosensors contain various fluorophore signaling units such as binaphthyl, anthracene, pyrene, tryptophan, benzimidazole, terpyridine, acridine, phenazine, acridone, BODIPY, and another conjugated aromatic one.

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Zinc(II) complex of terpyridine-crown macrocycle: A new motif in fluorescence sensing of zwitterionic amino acids

Cited by 50 publications

References 36 publications

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Fluorescent/luminescent detection of natural amino acids by organometallic systems

Optically active crown ether‐based fluorescent sensor molecules: A mini‐review

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