by Keith W. Bentley, Peng Zhang, and Christian Wolf

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Supplementary Fig. S2 Elution profiles of amino acid derivatives in a UPLC system. The enzyme (1 μg) was incubated with 10 mM D -amino acid (2.5 mM D -Tyr)

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Presentation transcript:

by Keith W. Bentley, Peng Zhang, and Christian Wolf Miniature high-throughput chemosensing of yield, ee, and absolute configuration from crude reaction mixtures by Keith W. Bentley, Peng Zhang, and Christian Wolf Science Volume 2(2):e1501162 February 12, 2016 Copyright © 2016, The Authors

Scheme 1 Concept of chirality sensing and asymmetric reaction analysis with a stereodynamic CD/fluorescence chemosensor and synthesis of bis(2-hydroxy-1-naphthyl)ketone, 1. Concept of chirality sensing and asymmetric reaction analysis with a stereodynamic CD/fluorescence chemosensor and synthesis of bis(2-hydroxy-1-naphthyl)ketone, 1. Keith W. Bentley et al. Sci Adv 2016;2:e1501162 Copyright © 2016, The Authors

Fig. 1 Chiroptical sensing of amines, amino alcohols, and amino acids. Chiroptical sensing of amines, amino alcohols, and amino acids. Top: General CD sensing scheme and substrate scope (only one enantiomer of each substrate is shown) of the zinc complex of 1. Middle: (A) CD spectra of the Zn complex derived from 1 and (1R,2R)-4 (blue) and (1S,2S)-4 (red). (B) CD response to (R)-6 (blue) and (S)-6 (red). (C) CD response to (R)-9 (blue) and (S)-9 (red). Bottom: (D) CD spectra of the Zn complex derived from 1 and nonracemic samples of 14. (E) Plots of the CD amplitudes at 338 nm (blue), 385 nm (red), and 445 nm (green) versus ee. (F) Plot of the fluorescence intensity of the Zn complex derived from 1 and varying equivalents of 14. All CD spectra were collected at 1 mM in diethyl ether. Keith W. Bentley et al. Sci Adv 2016;2:e1501162 Copyright © 2016, The Authors

Fig. 2 Chiroptical sensing of carboxylic acids, hydroxy acids, and diols. Chiroptical sensing of carboxylic acids, hydroxy acids, and diols. Top: Substrate scope using 1 with Me3Al (19 to 24) or Ti(Oi-Pr)4 (25 to 29). Only one enantiomer is shown. Middle: (A) CD spectra of the Al complex derived from 1 and (R)-22 (blue) and (S)-22 (red). (B) Sensor response to (R)-23 (blue) and (S)-23 (red). (C) CD spectra of the Ti complex derived from 1 and (1R,2R)-25 (blue) and (1S,2S)-25 (red). An equivalent of Et3N was added to α-hydroxy acids before analysis. (D) Fluorescence intensity of the Ti complex derived from 1 and varying molar equivalents of 25. (E) Plot of the fluorescence intensity at 600 nm of the Ti complex derived from 1 and varying amounts of 25. (F) Plots of the ICD amplitudes at 375 nm (red) and 470 nm (blue) for the Ti complex derived from 1 and nonracemic samples of 25. (G) ICD intensity at 375 nm (triangles) and 470 nm (diamonds) for the complex obtained from Ti(Oi-Pr)4, 1, and various amounts of (1R,2R)-25 (blue) and (1S,2S)-25 (red). All spectra were collected at 1 mM in diethyl ether. Bottom: Thermodynamically controlled Ti complex formation and equilibrium between homochiral species observed by ESI-MS using (1S,2S)-25 and (2R,3R)-26. Keith W. Bentley et al. Sci Adv 2016;2:e1501162 Copyright © 2016, The Authors

Table 3 Comparison of the yield, ee, and absolute configuration of hydrobenzoin obtained by AD of stilbene. Comparison of the yield, ee, and absolute configuration of hydrobenzoin obtained by AD of stilbene. Keith W. Bentley et al. Sci Adv 2016;2:e1501162 Copyright © 2016, The Authors