Investigation of Novel Peptide Chiral Selectors Prepared by Solid-Phase Synthesis with a tert-Butoxycarbonyl Amino Acid

Abstract

A new class of chiral stationary phases (CSP) with peptide chiral selectors was prepared by solid-phase synthesis with a tert-butoxycarbonyl-L-amino acid on silica. The type of amino acid that is favorable for this class of CSP is discussed. Using the CSP with the phenylalanine peptide selector, the effect of peptide length on the enantioselectivity was investigated in normal-phase mode. The applicability of the CSP with a phenylalanine peptide to chiral ligand-exchange chromatography was also examined.

Development and Pharmaceutical Applications of Functional Stationary Phases for Capillary Electrochromatography and Chiral Separation

“…Also, Chen used poly(N-benzyl-L-glutamine)-coated silica for the chiral separation of hydantoins [35]. We developed a novel CSP with phenylalanine (Phe) peptide as chiral selector [36][37][38]. The CSP was prepared on APS by solid-phase synthesis with tert-butoxycarbonyl (Boc) amino acids.…”

Effects of Temperature and Mobile Phase Condition on Chiral Recognition of Poly(l-phenylalanine) Chiral Stationary Phase

“…Boc-L-Phe (1.5 g), DCC (1.23 g) and DIEA (100 L) were added to a suspension of APS (0.7 mmol/g, 5 g) and DCM (25 m L) and the mixture was stirred at room temperature for 2 h. Boc groups were then removed from Phe residues with TFA (25% in DCM). The same procedure was repeated seven times to obtain an octapeptide selector on APS [APS-(Phe) 8 -H]. APS-(Phe) 8 …”

“…The same procedure was repeated seven times to obtain an octapeptide selector on APS [APS-(Phe) 8 -H]. APS-(Phe) 8 …”

“…To date, CSPs with several chiral selectors, such as cyclodextrins [1], macrocyclic antibiotics [2], polysaccharide derivatives [3], modified amino acids [4], proteins [5] and cinchona alkaloids [6], have been reported and some of them are commercially available. We recently developed new series of the CSPs having poly(L-Phe) peptide selector and successfully applied for chiral separations of some pharmaceuticals in reversed-and normal-phase modes [7,8]. Previous study suggests that the octapeptide selector is the best and the series of selectors are mainly in the -helical state and this conformation partially contributes to chiral recognition [7].…”

Investigation of peptoid chiral stationary phases varied in absolute configuration

“…Especially, polymeric or oligomeric CSPs that can usually provide excellent enantioselectivity and sample loading ability attracted much more attention, such as CSPs based on derived polysaccharide [3,4], cyclodextrin [5,6], protein [7][8][9][10], oligopeptide [11,12], network polymer [13,14], polymeric diamine derivative [15][16][17] and so on. The ordered secondary structure of polymer selector is generally considered very important in enantiorecognitions [12,[18][19][20].…”