Chiroptical sensing of unprotected amino acids, hydroxy acids, amino alcohols, amines and carboxylic acids with metal salts

Lynch, Ciarán C.; Santos, Zeus A. De los; Wolf, Christian

doi:10.1039/c9cc02525a

Cited by 20 publications

(12 citation statements)

References 52 publications

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“…[18][19][20][21][22] This phenomenon has been recently exploited in a novel chiroptical ee sensing technique which is based on the detection of induced visible ECD bands by complexation of transition metal ions with chiral organic analytes. 24,25 In addition to transition metal ions, it has also been shown that alkali (Li + , Na + , K + ) and alkaline earth metal ions (Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ ) [26][27][28][29][30][31][32][33] have a tendency to form complexes with hydroxycarboxylates. Their presence in solutions of HCAs was shown to induce changes in the intensity and Abstract: Electronic circular dichroism (ECD) and anisotropy spectra carry information on differential absorption of leftand right-circularly polarised light (LCPL and RCPL) by optically active compounds.…”

Section: Introductionmentioning

confidence: 99%

Concentration and pH effect on the electronic circular dichroism and anisotropy spectra of aqueous solutions of glyceric acid calcium salt

et al. 2021

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Electronic circular dichroism (ECD) and anisotropy spectra carry information on differential absorption of left-and right-circularly polarized light (LCPL and RCPL) by optically active compounds. This makes them powerful tools for the rapid determination of enantiomeric excesses (ee) in asymmetric synthetic and pharmaceutical chemistry, as well as for predicting the ee inducible by ultraviolet (UV) CPL. The ECD response of a chiral molecule is, however, critically dependent on the properties of the surrounding medium. Here, we report on the first ECD/anisotropy spectra of aqueous solutions of the calcium salt dihydrate of glyceric acid. A systematic study of the effect of the salt concentration and pH on the chiroptical response revealed significant changes and the appearance of a new ECD band of opposite sign. Based on the literature, this can be rationalized by the increase in the relative proportion of free glyceric acid/glycerate to Ca 2+ complexes with glycerate with decreasing salt concentration or pH. Glyceric acid can be readily produced under astrophysical conditions. The anisotropy spectra of the solution containing prevalently the free form of this dihydroxy carboxylic acid resemble the ones of previously investigated aliphatic chain hydroxycarboxylic acids and proteinogenic amino acids. This indicates possible common handedness of stellar CPL-induced asymmetry in the potential comonomers of primitive proto-peptides.alkaline earth metal, chiral hydroxycarboxylic acid, circularly polarized light, complexation, CPL scenario, enantiomeric excess, homochirality | INTRODUCTIONDifferentiation between enantiomers of a chiral species requires a chiral force. Circularly polarized light (CPL) represents a true chiral entity, 1 and the origin of biological homochirality-uniformity of handedness of amino [This article is part of the Special Issue: Chirality in France. See the first articles for this special issue previously published in Volumes 33:9, 33:10, 33:11, 33:12, and 34:1. More special articles will be found in this issue as well as in those to come.]

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Section: Introductionmentioning

confidence: 99%

Concentration and pH effect on the electronic circular dichroism and anisotropy spectra of aqueous solutions of glyceric acid calcium salt

et al. 2021

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“…In accordance with our chiral amine sensing study, these additional 21 substrates were selected to encompass structures exhibiting asmall aromatic ring as well as some that are devoid of ac hromophore and therefore increasingly challenging.N evertheless,d istinct CD effects were obtained without exception just by fast mixing of the assay components and CD analysis without further delay (see SI). [19,[38][39][40][41][42][43] Scheme 1. Chiroptical redox switching using NaBH 4 and air as external stimuli.…”

Section: Methodsmentioning

confidence: 99%

Chiroptical Switching and Quantitative Chirality Sensing with (Pseudo)halogenated Quinones

Formen

Wolf

2021

Angewandte Chemie

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Pseudo)halogenated quinones react smoothly with chiral amines,amino alcohols,and amino acids toward pushpull conjugates with optical sensing and switching applications. The chiroptically active conjugates serve as redox switches between two reversibly interconverting states with remarkably different UV and CD signatures.A ddition of sodium borohydride generates ahydroquinone derivative that is quantitatively re-oxidized to the original quinone upon exposure to air.This chiroptical quinone/hydroquinone redox switch system combines several attractive features such as simple set-up,u se of inexpensive chemicals,s hort response time,a nd thermal and photochemical stability.Aconceptually new sensing approach that is based on integrated chiroptical amplification and redox switching enables on-the-fly deconvolution of otherwise overlapping CD spectra and is used for quantitative er analysis of challenging samples containing constitutional isomers in varying enantiomeric compositions.

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“…Therefore, recognizing chiral enantiomers is of great significance for drug design and understanding the metabolism and regulation in organisms. At present, the identification and resolution of chiral molecules are usually achieved by means of high-performance liquid chromatography [ 3 ], capillary electrophoresis [ 4 ], electrochemistry [ 5 ], and circular dichroism [ 6 ], which are often time-consuming, require cost-ineffective equipment, produce low responses, and present difficulty achieving real-time online analysis. Consequently, the development of a new type of enantiomer recognition platform is key to meeting the needs of label-free, highly sensitive, fast-response detection.…”

Section: Introductionmentioning

confidence: 99%

Construction and Application of Graphene Oxide-Bovine Serum Albumin Modified Extended Gate Field Effect Transistor Chiral Sensor

Xiao

et al. 2021

Sensors

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Chirality is an essential natural attribute of organisms. Chiral molecules exhibit differences in biochemical processes, pharmacodynamics, and toxicological properties, and their enantioselective recognition plays an important role in explaining life science processes and guiding drug design. Herein, we developed an ultra-sensitive enantiomer recognition platform based on an extended-gate metal-oxide semiconductor field-effect-transistor (Nafion–GO@BSA–EG-MOSFET) that achieved effective chiral resolution of ultra-sensitive Lysine (Lys) and α-Methylbenzylamine (α-Met) enantiodiscrimination at the femtomole level. Bovine serum albumin (BSA) was immobilized on the surface of graphene oxide (GO) through amide bond coupling to prepare the GO@BSA complex. GO@BSA was drop-cast on deposited Au surfaces with a Nafion solution to afford the extended-gate sensing unit. Effective recognition of chiral enantiomers of mandelic acid (MA), tartaric acid (TA), tryptophan (Trp), Lys and α-Met was realized. Moreover, the introduction of GO reduced non-specific adsorption, and the chiral resolution concentration of α-Met reached the level of picomole in a 5-fold diluted fetal bovine serum (FBS). Finally, the chiral recognition mechanism of the as-fabricated sensor was proposed.

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Chiroptical sensing of unprotected amino acids, hydroxy acids, amino alcohols, amines and carboxylic acids with metal salts

Abstract: Optical chirality sensing of unprotected amino acids, hydroxy acids, amino alcohols, amines and carboxylic acids based on a practical mix-and-measure protocol with readily available copper, iron, palladium, manganese, cerium or rhodium salts is demonstrated.

Cited by 20 publications

References 52 publications

Concentration and pH effect on the electronic circular dichroism and anisotropy spectra of aqueous solutions of glyceric acid calcium salt

Concentration and pH effect on the electronic circular dichroism and anisotropy spectra of aqueous solutions of glyceric acid calcium salt

Chiroptical Switching and Quantitative Chirality Sensing with (Pseudo)halogenated Quinones

Construction and Application of Graphene Oxide-Bovine Serum Albumin Modified Extended Gate Field Effect Transistor Chiral Sensor

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