US 12,486,293 B2
Chirality sensing with molecular click chemistry probes
Christian Wolf, Arlington, VA (US); Fathima Yushra Thanzeel, Washington, DC (US); and Kaluvu Balaraman, Arlington, VA (US)
Assigned to GEORGETOWN UNIVERSITY, Washington, DC (US)
Appl. No. 17/265,147
Filed by GEORGETOWN UNIVERSITY, Washington, DC (US)
PCT Filed Jul. 30, 2019, PCT No. PCT/US2019/044189
§ 371(c)(1), (2) Date Feb. 1, 2021,
PCT Pub. No. WO2020/028396, PCT Pub. Date Feb. 6, 2020.
Claims priority of provisional application 62/712,150, filed on Jul. 30, 2018.
Prior Publication US 2022/0380395 A1, Dec. 1, 2022
Int. Cl. C07F 9/00 (2006.01); C07D 311/18 (2006.01); C07F 9/52 (2006.01); C07F 9/6574 (2006.01); C07F 9/6584 (2006.01); G01N 21/33 (2006.01)
CPC C07F 9/65848 (2013.01) [C07D 311/18 (2013.01); C07F 9/52 (2013.01); C07F 9/65744 (2013.01); G01N 21/33 (2013.01)] 25 Claims
OG exemplary drawing
 
1. An analytical method comprising:
providing a sample containing a chiral analyte that can exist in stereoisomeric forms;
providing an achiral probe selected from the group consisting of coumarin-derived Michael acceptors, dinitrofluoroarenes and analogs thereof, arylsulfonyl chlorides and analogs thereof, arylchlorophosphines and analogs thereof, aryl halophosphites, and halodiazaphosphites;
contacting the sample with the probe under conditions to permit covalent binding of the probe to the analyte; and
performing a first spectroscopic analysis using one of circular dichroism (CD), optical rotatory dispersion and polarimetry, and/or a second spectroscopic analysis using one of ultraviolet (UV) spectroscopy and fluorescence spectroscopy to obtain, based on any covalent binding that occurs during said contacting, one or more of an absolute configuration of the analyte in the sample, concentration of the analyte in the sample, and an enantiomeric composition of the analyte in the sample.