Chiral recognition of cyclic α‐hydroxyketones by CD‐sensitive zinc tetraphenylporphyrin tweezer

Ishii, Hideki; Chen, Yihui; Miller, Ross A.; Karady, Sandor; Nakanishi, Koji; Berova, Nina

doi:10.1002/chir.20166

Cited by 26 publications

(24 citation statements)

References 42 publications

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“…As in previous reports, [5][6][7][8] distribution graphs of (dihedral angle values y have been plotted. For the first time in this type of analysis, values of y are plotted against the Boltzmann population of the corresponding structure.…”

Section: Molecular Modeling Protocolmentioning

confidence: 99%

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CD‐sensitive Zn‐porphyrin tweezer host‐guest complexes, part 1: MC/OPLS‐2005 computational approach for predicting preferred interporphyrin helicity

et al. 2009

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This article describes a computational study on dimeric zinc porphyrin tweezer complexes with primary/secondary amines and secondary alcohols that validates the use of Optimized Potential for Liquid Simulations (OPLS-2005) as the lead computational choice for assisting the tweezer methodology in the absolute configurational assignment of organic compounds. A supramolecular, microscale approach known as the tweezer method has been widely applied in the past decade for determining the absolute configuration of chiral substrates that are difficult to study by other readily available methods. The method relies on a host/guest complexation mechanism between a porphyrin tweezer moiety and a substrate, after its conversion into a bidentate conjugate. The formation of 1:1 complexes is a stereodifferentiating process: upon complexation, the originally achiral tweezer adopts a preferential interporphyrin helicity, dictated by the absolute configuration of the chiral substrate. By correctly predicting the sign of the interporphyrin helicity in the complex, OPLS-2005 provides a correlation between the observed circular dichroism (CD) signal and the absolute configuration of the substrate. It also offers a great degree of insight into the structural factors responsible for chiral recognition and the amplitude of exciton couplets. Moreover, the preferential binding sites between the Zn-tweezer and secondary amine conjugates were revealed by using the new computational approach.

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Section: Molecular Modeling Protocolmentioning

confidence: 99%

“…The substrates from which the conjugates are derived play important biological roles 5,[36][37][38][39] and belong to the secondary amine, primary amine and secondary alcohol families: (7), and (S)-methyl 2-(2-(3-aminopropylamino)acetamido)propanoate (8), presented in Figure 3.…”

Section: Introductionmentioning

confidence: 99%

CD‐sensitive Zn‐porphyrin tweezer host‐guest complexes, part 1: MC/OPLS‐2005 computational approach for predicting preferred interporphyrin helicity

et al. 2009

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“…Much more sensitive chirality "sensing" was achieved by forming supramolecular complexes of primary chiral amines with pentanediol-linked zinc porphyrins, referred to as a "zinc porphyrin tweezer" [17,40,41], as shown in Fig. 6.…”

Section: Zinc Porphyrin Tweezersmentioning

confidence: 99%

Transition metal-based chiroptical switches for nanoscale electronics and sensors

Canary

Mortezaei

Liang

2010

Coordination Chemistry Reviews

127

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“…[1][2][3][4][5] There has also been growing interest in recent years in applying faster and easy-to-use spectroscopic techniques to determine chiral purity, that is, the enantiomeric excess (%ee) of a particular enantiomer in an enantiomer mixture. [6][7][8][9][10] This growing interest can be attributed to modern drug discoveries that demand quicker synthesis of chiral compounds. Consequently, these discoveries have led to a desire for faster and more efficient chiral analysis tools.…”

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confidence: 99%

Determination of the enantiomeric excess of an M3 antagonist drug substance by chemometric analysis of the IR spectra of different guest‐host complexes

et al. 2006

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A novel approach for the potential on-line determination of the enantiomeric excess (ee) of an M3 antagonist drug substance combining attenuated total reflectance infrared (ATR-IR) spectroscopy, guest-host complexes, and chemometric data analysis is described. Chiral recognition through a formation of diastereomeric complexes was measured by ATR-IR. Small changes on the IR spectra reflect the interaction between the guest (M3) and host (chiral selector). These changes are measured as a function of M3 enantiomer excess. The standard error of prediction is 1.3 ee%. The prediction results based on the IR method were in good agreement with the gravimetric method. The robustness of the calibration model was evaluated by varying the concentration of the chiral selector, the pH of the solution, and the organic solvents. The stability of the calibration model was also demonstrated through measuring different sets of samples on different days.

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Chiral recognition of cyclic α‐hydroxyketones by CD‐sensitive zinc tetraphenylporphyrin tweezer

Cited by 26 publications

References 42 publications

CD‐sensitive Zn‐porphyrin tweezer host‐guest complexes, part 1: MC/OPLS‐2005 computational approach for predicting preferred interporphyrin helicity

CD‐sensitive Zn‐porphyrin tweezer host‐guest complexes, part 1: MC/OPLS‐2005 computational approach for predicting preferred interporphyrin helicity

Transition metal-based chiroptical switches for nanoscale electronics and sensors

Determination of the enantiomeric excess of an M3 antagonist drug substance by chemometric analysis of the IR spectra of different guest‐host complexes

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