Transitioning enantioselective indicator displacement assays for alpha-amino acids to protocols amenable to high-throughput screening.

Journal of the American Chemical Society
Diana Leung, Eric V Anslyn

Abstract

Enantioselective indicator displacement assays (eIDAs) for alpha-amino acids were conducted in a 96-well plate format to demonstrate the viability of the technique for the high-throughput screening (HTS) of enantiomeric excess (ee) values. Chiral receptors [Cu(II)(1)](2+) and [Cu(II)(2)](2+) with the indicator chrome azurol S were implemented for the eIDAs. Enantiomeric excess calibration curves were made using both receptors and then used to analyze true test samples. These results were compared to those previously obtained with a conventional UV-vis spectrophotometer, and they showed little to no loss of accuracy, while the speed of analysis was increased. A sample of valine of unknown ee was synthesized through an asymmetric reaction to produce a realistic reaction sample, which was analyzed using receptor [Cu(II)(1)](2+). The experimentally determined ee using our eIDA was compared to that obtained by chiral HPLC and (1)H NMR chiral shift reagent analysis. This gave errors of 4.7% and 12.0%, respectively. In addition to the use of ee calibration curves, an artificial neural network (ANN) was used to determine the % L-amino acid of the test samples and of the sample of valine of unknown ee from the asymmetric reaction. This ...Continue Reading

Citations

Mar 5, 2011·The Journal of Organic Chemistry·Takuya MatsumotoTetsuo Nagano
Feb 19, 2009·The Journal of Organic Chemistry·Hai-Ming Guo, Fujie Tanaka
May 19, 2016·Organic Letters·Huayin HuangHongjun Fan
Oct 5, 2016·Journal of the American Chemical Society·Zeus A De Los Santos, Christian Wolf
Sep 8, 2010·Chemical Society Reviews·Pavel AnzenbacherMaria E Kozelkova
Jul 12, 2011·Organic & Biomolecular Chemistry·Xia YangYixiang Cheng
Sep 6, 2011·Chemical Society Reviews·Diana LeungEric V Anslyn
Jun 28, 2019·Organic & Biomolecular Chemistry·Samantha L PilicerChristian Wolf
Feb 20, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Huiyeong JuYoichi Habata
Oct 16, 2012·Chemical Communications : Chem Comm·Daniel P Iwaniuk, Christian Wolf
May 21, 2010·Analytical Chemistry·David K BwambokIsiah M Warner
Jun 19, 2021·Organic & Biomolecular Chemistry·Ishfaq Ahmad Rather, Rashid Ali
Sep 9, 2010·The Journal of Organic Chemistry·Daniel P Iwaniuk, Christian Wolf
Feb 27, 2015·Chemical Reviews·Lei YouEric V Anslyn
Feb 14, 2012·Organometallics·Sung Ok KangEric V Anslyn
Oct 1, 2019·Journal of the American Chemical Society·F Yushra ThanzeelChristian Wolf

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