Pattern-based recognition for the rapid determination of identity, concentration, and enantiomeric excess of subtly different threo diols.
A pattern-based recognition approach for the rapid determination of the identity, concentration, and enantiomeric excess of chiral vicinal diols, specifically threo diols, has been developed. A diverse enantioselective sensor array was generated using three chiral boronic acid receptors and three pH indicators. The optical response produced by the sensor array was analyzed by two pattern-recognition algorithms: principal component analysis and artificial neural networks. Principal component analysis demonstrated good chemoselective and enantioselective separation of the analytes, and an artificial neural network was used to accurately determine the concentrations and enantiomeric excesses of five unknown samples with an average absolute error of +/-0.08 mM in concentration and 3.6% in enantiomeric excess. The speed of the analysis was enhanced by using a 96-well plate format, portending applications in high-throughput screening for asymmetric-catalyst discovery. X-ray crystallography and (11)B NMR spectroscopy was utilized to study the enantioselective nature of the boronic acid host 2.
Shabbir
Shagufta H
SH
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
Joyce
Leo A
LA
da Cruz
Gabriella M
GM
Lynch
Vincent M
VM
Sorey
Steven
S
Anslyn
Eric V
EV
D000438:Alcohols / Q000032:analysis*; D001897:Boronic Acids / Q000737:chemistry; D002623:Chemistry Techniques, Analytical / Q000191:economics / Q000379:methods*; D015394:Molecular Structure; D010363:Pattern Recognition, Automated / Q000191:economics / Q000379:methods*; D013237:Stereoisomerism
D000438:Alcohols; D001897:Boronic Acids
Chem Rev. 2000 Jul 12;100(7):2649-78
11749299
Org Lett. 2001 May 3;3(9):1311-4
11348222
Angew Chem Int Ed Engl. 2003 May 9;42(18):2070-2
12746826
Angew Chem Int Ed Engl. 2003 Dec 15;42(48):5984-7
14679549
J Am Chem Soc. 2006 May 3;128(17):5652-3
16637629
Proc Natl Acad Sci U S A. 2009 Jun 30;106(26):10487-92
19332790
J Am Chem Soc. 2006 Feb 1;128(4):1222-32
16433539
Angew Chem Int Ed Engl. 2004 Sep 27;43(38):5013-6
15384110
J Am Chem Soc. 2005 Jun 22;127(24):8610-1
15954763
Chemistry. 2007;13(1):99-104
17066491
J Am Chem Soc. 2008 Sep 17;130(37):12328-33
18714993
J Am Chem Soc. 2001 Sep 19;123(37):9206-7
11552847
J Am Chem Soc. 2007 Jun 20;129(24):7538-44
17530846
J Am Chem Soc. 2006 Feb 22;128(7):2421-5
16478197
J Org Chem. 2009 Jun 5;74(11):4055-60
19391608
Cell Mol Life Sci. 2006 Jul;63(13):1465-75
16732429
Chemistry. 2004 Aug 6;10(15):3792-804
15281164
Angew Chem Int Ed Engl. 2002 Jan 4;41(1):124-7
12491459
J Am Chem Soc. 2008 Jul 23;130(29):9232-3
18572934
Nature. 2000 Aug 17;406(6797):710-3
10963592
Anal Chem. 2007 Jun 15;79(12):4716-9
17511423
Org Lett. 2006 May 11;8(10):1971-4
16671759
Org Lett. 2005 Aug 4;7(16):3441-4
16048312
J Am Chem Soc. 2004 Mar 31;126(12):3676-7
15038696
Angew Chem Int Ed Engl. 2001 Sep 3;40(17):3118-3130
29712042
Science. 2000 Oct 13;290(5490):307-13
11030644
J Am Chem Soc. 2005 Mar 30;127(12):4260-9
15783208