Chiral separations using dipeptide polymerized surfactants: effect of amino acid order

Analytical Chemistry
E J BilliotI M Warner

Abstract

Chiral separations using various polymerized dipeptide surfactants in electrokinetic capillary chromatography (EKC) are investigated. The two main dipeptide surfactants used in this study were sodium N-undecylenyl-L-valine-L-leucine (L-SUVL), and sodium N-undecylenyl-L-leucine-L-valine (L-SULV). These studies were performed in order to determine if the order of amino acids in dipeptide surfactants is important in terms of chiral recognition and separations. Both the monomer and the polymer of these two surfactants were compared for the separation of two model atropisomers, (+/-)-1,1-bi-2-naphtol (BOH) and (+/-)-1,1'-bi-2-naphthyl-2,2'-diyl hydrogen phosphate (BNP). Some advantages and disadvantages of the polymer relative to the monomer are discussed. Four other surfactants, the polymers of sodium N-undecylenyl-L-leucine-L-leucine (L-SULL), sodium N-undecylenyl-L-valine-L-valine (L-SUVV), sodium N-undecylenyl-L-valine (L-SUV), and sodium N-undecylenyl-L-leucine (L-SUL), were also used in this study, and their performance was compared to that of poly(L-SULV). These data show conclusively that the order of amino acids in dipeptide surfactants has a dramatic effect on chiral recognition. Our investigations indicate that poly-(L-SU...Continue Reading

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Citations

May 11, 2005·Analytical and Bioanalytical Chemistry·Louis BluhmTingyu Li
Aug 7, 2001·Journal of Chromatography. a·F H BilliotI M Warner
Sep 28, 1999·Pharmaceutical Science & Technology Today·E C Soo de Biasi V
May 7, 2002·Journal of Chromatography. a·Fereshteh Haddadian BilliotIsiah M Warner
Aug 21, 2013·Open Journal of Physical Chemistry·Kevin F MorrisYayin Fang
Feb 18, 2012·Journal of Chromatographic Science·Andriana S ConstantinouConstantina P Kapnissi-Christodoulou
Oct 7, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Tetsuo Okada
Nov 20, 2012·Electrophoresis·Despina A TsioupiConstantina P Kapnissi-Christodoulou
Feb 24, 2001·Electrophoresis·G Gübitz, M G Schmid
Jan 6, 2010·Magnetic Resonance in Chemistry : MRC·Stephanie A KingsburyKevin F Morris
Jan 20, 2006·Electrophoresis·Carmen García-Ruiz, María Luisa Marina
Jan 10, 2012·Electrophoresis·Despina A TsioupiConstantina P Kapnissi-Christodoulou
Dec 22, 1999·Electrophoresis·V Kasicka
May 14, 2018·Chemistry and Physics of Lipids·William M Penny, Christopher P Palmer
Sep 1, 2006·The Journal of Physical Chemistry. B·Kevin F MorrisCynthia K Larive
Sep 29, 2000·Analytical Chemistry·T J Ward

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