Application of a high-throughput enantiomeric excess optical assay involving a dynamic covalent assembly: parallel asymmetric allylation and ee sensing of homoallylic alcohols

Jo, Hyun Hwa; Gao, Xiaohui; You, Lei; Anslyn, Eric V.; Krische, Michael J.

doi:10.1039/c5sc02416a

Cited by 42 publications

(32 citation statements)

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“…However, the large number of low-selectivity sensors is the key to overcome the problem of complicated matrixes. [12][13][14][15][16][17][18] The discrimination made by the receptors is achieved by a characteristic "ngerprint" related to each system sensor analyte. This characteristic pattern is usually represented by an ensemble of parameters which are not easily described via simple calibration methods.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular cages as differential sensors for dicarboxylate anions: guest length sensing using principal component analysis of ESI-MS and ¹H-NMR raw data

et al. 2019

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Section: Introductionmentioning

confidence: 99%

Supramolecular cages as differential sensors for dicarboxylate anions: guest length sensing using principal component analysis of ESI-MS and ¹H-NMR raw data

et al. 2019

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“…Anslyn [30][31][32][33][34][35][36] and their co-workers with tris(2-pyridylmethyl)amine (TPMA) metal complexes.…”

Section: Introductionmentioning

confidence: 99%

Second‐Generation Tris(2‐pyridylmethyl)amine–Zinc Complexes as Probes for Enantiomeric Excess Determination of Amino Acids

et al. 2017

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Self‐assembly through imine condensation chemistry in combination with metal coordination is becoming one of the leading strategies for the preparation of stereodynamic probes for the determination of enantiomeric excess. Recently, we reported a novel molecular architecture based on a modified tris(2‐pyridylmethyl)amine–zinc(II) complex [TPMA = tris(2‐pyridylmethyl)amine] that is able to function as an optical probe for the determination of the enantiomeric excess of amino acids. Herein, we report on how a slight modification of the TPMA ligand enhances both the dichroic response and the stability of the system. The novel probe provides a much higher dichroic signal compared with the previously reported system.

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“…The addition of a chiral analyte leads preferentially to the formation of one diasteroisomer that furnishes back the optical chiral information. Within these stereodynamic probes, tris(2‐pyridylmethyl)amine (TPMA)–based metal complexes have shown to be versatile chemical systems for the determination of ee . This ligand assumes a propeller‐like arrangement around the metal center that in solution is in equilibrium between the two helical configurations (clockwise and counterclockwise).…”

Section: Introductionmentioning

confidence: 99%

“…Within these stereodynamic probes, tris(2-pyridylmethyl)amine (TPMA)-based metal complexes have shown to be versatile chemical systems for the determination of ee. [16][17][18][19][20][21][22] This ligand assumes a propeller-like arrangement around the metal center that in solution is in equilibrium between the two helical configurations (clockwise and counterclockwise). In the presence of a suitable analyte, one [This article is part of the Special Thematic Issue in Memory of Ettore Castiglioni: Chiroptical Spectroscopy: Instrumentation, Experimental Aspects and Application.…”

Section: Introductionmentioning

confidence: 99%

A stereodynamic fluorescent probe for amino acids. Circular dichroism and circularly polarized luminescence analysis

et al. 2017

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The use of stereodynamic probes is becoming one of the leading strategies for the fast and effective determination of enantiomeric excess. Recently, we reported a series of novel molecular architectures based on a modified tris(2-pyridylmethyl)amine complex (TPMA), which are able to amplify the electronic CD, in the case of Zn(II) assemblies and vibrational CD, in the case of Co(II) assemblies. Herein, we report a structural modification of the ligand with the purpose to obtain a fluorescent chiral probe. The study deals with the synthesis of the novel ligand, the formation of the self-assembly system with amino acids, and the study of the electronic CD and circularly polarized luminescence. KEYWORDS CD, CPL, enantiomeric excess, self-assembly, supramolecular chemistry | INTRODUCTIONIn the last few decades, several research groups have been studying chiral sensors because of the important applications that chiral molecules have in several fields of science, ranging from catalysis to materials. Under this respect, special attention has been paid to searching new methods and techniques for the determination of enantiomeric excess (ee) that are faster and cheaper than traditional chromatographic methods. [1][2][3][4] In this context, several supramolecular architectures have been developed to gather an optical signal that can be easily measured through the most common spectroscopic techniques, ie, circular dichroism (CD). [5][6][7][8][9][10][11][12][13][14][15] Usually, these supramolecular sensors possess at least one labile stereogenic element that interconverts between 2 enantiomeric forms. The addition of a chiral analyte leads preferentially to the formation of one diasteroisomer that furnishes back the optical chiral information. Within these stereodynamic probes, tris(2-pyridylmethyl)amine (TPMA)-based metal complexes have shown to be versatile chemical systems for the determination of ee. [16][17][18][19][20][21][22] This ligand assumes a propeller-like arrangement around the metal center that in solution is in equilibrium between the two helical configurations (clockwise and counterclockwise configuration is preferred, and the resulting diasteroisomer is able to provide a chiroptical signal. 23,24 Recently, we have started to combine the TPMA scaffold with dynamic covalent chemistry (DCC) of imines formation. [25][26][27][28][29]31 has already shown its fundamental role in the formation of new complex nano-architectures. In particular, we described two novel supramolecular architectures based on modified TPMA metal complexes (Scheme 1): the dinuclear 1-Zn-aa and 3-Zn-aa, and the trinuclears 2-Zn-aa and 2-Co-aa. These systems have shown to perform as probes for amino acids, 32-35 furnishing dichroic signals characteristic of the amino acidic side chain and proportional to the enantiomeric excess. While all systems are effective using electronic CD, the presence of cobalt(II) in 2-Co-aa induces additionally gigantic (or: huge) vibrational CD bands, allowing the measurement of a VCD spectrum in onl...

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Application of a high-throughput enantiomeric excess optical assay involving a dynamic covalent assembly: parallel asymmetric allylation and ee sensing of homoallylic alcohols

Abstract: Parallel synthesis and high-throughput ee screening.

Cited by 42 publications

References 50 publications

Supramolecular cages as differential sensors for dicarboxylate anions: guest length sensing using principal component analysis of ESI-MS and ¹H-NMR raw data

Supramolecular cages as differential sensors for dicarboxylate anions: guest length sensing using principal component analysis of ESI-MS and ¹H-NMR raw data

Second‐Generation Tris(2‐pyridylmethyl)amine–Zinc Complexes as Probes for Enantiomeric Excess Determination of Amino Acids

A stereodynamic fluorescent probe for amino acids. Circular dichroism and circularly polarized luminescence analysis

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Application of a high-throughput enantiomeric excess optical assay involving a dynamic covalent assembly: parallel asymmetric allylation and ee sensing of homoallylic alcohols

Abstract: Parallel synthesis and high-throughput ee screening.

Cited by 42 publications

References 50 publications

Supramolecular cages as differential sensors for dicarboxylate anions: guest length sensing using principal component analysis of ESI-MS and 1H-NMR raw data

Supramolecular cages as differential sensors for dicarboxylate anions: guest length sensing using principal component analysis of ESI-MS and 1H-NMR raw data

Second‐Generation Tris(2‐pyridylmethyl)amine–Zinc Complexes as Probes for Enantiomeric Excess Determination of Amino Acids

A stereodynamic fluorescent probe for amino acids. Circular dichroism and circularly polarized luminescence analysis

Contact Info

Product

Resources

About

Supramolecular cages as differential sensors for dicarboxylate anions: guest length sensing using principal component analysis of ESI-MS and ¹H-NMR raw data

Supramolecular cages as differential sensors for dicarboxylate anions: guest length sensing using principal component analysis of ESI-MS and ¹H-NMR raw data