title: Pattern-based recognition for the rapid determination of identity, concentration, and enantiomeric excess of subtly different threo diols.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
authors.forename: Shagufta H
authors.initials: SH
authors.lastname: Shabbir
authors.forename: Leo A
authors.initials: LA
authors.lastname: Joyce
authors.forename: Gabriella M
authors.initials: GM
authors.lastname: da Cruz
authors.forename: Vincent M
authors.initials: VM
authors.lastname: Lynch
authors.forename: Steven
authors.initials: S
authors.lastname: Sorey
authors.forename: Eric V
authors.initials: EV
authors.lastname: Anslyn
mesh_terms: 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
chemical_list: D000438:Alcohols; D001897:Boronic Acids
references.citation: Chem Rev. 2000 Jul 12;100(7):2649-78
references.pmid: 11749299
references.citation: Org Lett. 2001 May 3;3(9):1311-4
references.pmid: 11348222
references.citation: Angew Chem Int Ed Engl. 2003 May 9;42(18):2070-2
references.pmid: 12746826
references.citation: Angew Chem Int Ed Engl. 2003 Dec 15;42(48):5984-7
references.pmid: 14679549
references.citation: J Am Chem Soc. 2006 May 3;128(17):5652-3
references.pmid: 16637629
references.citation: Proc Natl Acad Sci U S A. 2009 Jun 30;106(26):10487-92
references.pmid: 19332790
references.citation: J Am Chem Soc. 2006 Feb 1;128(4):1222-32
references.pmid: 16433539
references.citation: Angew Chem Int Ed Engl. 2004 Sep 27;43(38):5013-6
references.pmid: 15384110
references.citation: J Am Chem Soc. 2005 Jun 22;127(24):8610-1
references.pmid: 15954763
references.citation: Chemistry. 2007;13(1):99-104
references.pmid: 17066491
references.citation: J Am Chem Soc. 2008 Sep 17;130(37):12328-33
references.pmid: 18714993
references.citation: J Am Chem Soc. 2001 Sep 19;123(37):9206-7
references.pmid: 11552847
references.citation: J Am Chem Soc. 2007 Jun 20;129(24):7538-44
references.pmid: 17530846
references.citation: J Am Chem Soc. 2006 Feb 22;128(7):2421-5
references.pmid: 16478197
references.citation: J Org Chem. 2009 Jun 5;74(11):4055-60
references.pmid: 19391608
references.citation: Cell Mol Life Sci. 2006 Jul;63(13):1465-75
references.pmid: 16732429
references.citation: Chemistry. 2004 Aug 6;10(15):3792-804
references.pmid: 15281164
references.citation: Angew Chem Int Ed Engl. 2002 Jan 4;41(1):124-7
references.pmid: 12491459
references.citation: J Am Chem Soc. 2008 Jul 23;130(29):9232-3
references.pmid: 18572934
references.citation: Nature. 2000 Aug 17;406(6797):710-3
references.pmid: 10963592
references.citation: Anal Chem. 2007 Jun 15;79(12):4716-9
references.pmid: 17511423
references.citation: Org Lett. 2006 May 11;8(10):1971-4
references.pmid: 16671759
references.citation: Org Lett. 2005 Aug 4;7(16):3441-4
references.pmid: 16048312
references.citation: J Am Chem Soc. 2004 Mar 31;126(12):3676-7
references.pmid: 15038696
references.citation: Angew Chem Int Ed Engl. 2001 Sep 3;40(17):3118-3130
references.pmid: 29712042
references.citation: Science. 2000 Oct 13;290(5490):307-13
references.pmid: 11030644
references.citation: J Am Chem Soc. 2005 Mar 30;127(12):4260-9
references.pmid: 15783208