Enantiorecognition ability of peptoids with α-chiral, aromatic side chains

Investigation of peptoid chiral stationary phases varied in absolute configuration

“…For example, based on separation factors, S-R-R form CSP 3 separated TR 4, TR 5 and TR 8 best; S-R-S form CSP 4 resolved TR 1, TR 3, TR 6 and TR 7 best; while S-S-R form CSP 5 separated TR 9 slightly better than others. Especially, most of these outstanding separations are observed exceed those obtained on previously reported (Nspe) 6 based CSP [24].…”

“…Binaphthol (TR 1) and some of its analogs can be well enantioseparated by peptoid CSPs [24,25]. Herein, significantly different separations of some axially chiral analytes are observed on CSPs varied in configuration form.…”

“…In our first paper, we investigated enantiorecognition abilities of peptoid CSPs varied in the chain length of selector [24]. Subsequently, through introducing achiral alkyl group or new chiral block as terminal motif of peptoid selector, we improved selectivity of peptoid CSP efficiently [25].…”

Improvement of peptoid chiral stationary phases by modifying the terminal group of selector

“…Stationary phase (Nspe) 4 -silica refers to CSP based on peptoid with four Nspe units and was prepared in our previous work [24]. The synthesis of CSP-1-CSP-7 is described in Supporting Information.…”

“…Peptoids are a diverse family of non-natural oligomers and were usually developed to mimic bioactive polypeptides by taking advantage of their structural similarities with peptides and more feasible modifications in structure [22,23]. Recently, we prepared and evaluated CSPs based on peptoids for the first time [24]. The previously investigated peptoid selectors were based on (S)-N-(1-phenylethyl)glycine (Nspe) monomer and varied in chain length from 3 to 7 chiral units.…”