Enantioseparation using amylose esters as chiral stationary phases for high-performance liquid chromatography

Abstract

Novel amylose ester derivatives were synthesized and their chiral recognition abilities as chiral stationary phases for highperformance liquid chromatography were evaluated. Compared with amylose benzoate derivatives, cinnamate derivatives showed a higher chiral recognition ability and some racemates could be efficiently resolved. The recognition abilities of these derivatives varied significantly depending on the types and positions of substituents introduced into the phenyl group. Among the prepared derivatives, the nonsubstituted cinnamate derivative showed a relatively high chiral recognition, and interestingly, its ability was influenced by the preparation conditions of packing materials using silica gel as a support.

Efficient Separation of Enantiomers Using Stereoregular Chiral Polymers

“…These findings initiated the systematic studies of the benzoate and phenylcarbamate derivatives of polysaccharides, particularly cellulose and amylose. A series of cellulose (60 in Figure 25) 203 and amylose tribenzoates (61 in Figure 25) 204 has been prepared in our group. The obtained cellulose tribenzoates with electrondonating substituents, such as an alkyl group, exhibited a higher chiral recognition ability than those with electron-withdrawing substituents, such as a halogen.…”

Chiral separation materials based on derivatives of 6‐amino‐6‐deoxyamylose

“…The ADMPC showed an enantioseparation capability, which was even higher than that of cellulose tris(3,5‐dimethylphenylcarbamate) (CDMPC). Since then, amylose derivatives have attracted much more attention in enantioseparation field, amylose tris(phenylcarbamate)s in particular 8–12 . Different from cellulose tris(benzoate)s, 13–15 such as cellulose tris(4‐methylbenozate), amylose tris(benzoate)s used as CSs were seldomly reported 8 .…”

“…Since then, amylose derivatives have attracted much more attention in enantioseparation field, amylose tris(phenylcarbamate)s in particular 8–12 . Different from cellulose tris(benzoate)s, 13–15 such as cellulose tris(4‐methylbenozate), amylose tris(benzoate)s used as CSs were seldomly reported 8 . The reason might be that amylose tris(benzoate)s were not versatile in chiral recognition 16 .…”

Highly C6-selective and quantitative modification of cellulose: nucleoside-appended celluloses to solubilize single walled carbon nanotubes

“…Many research groups have launched their intense research efforts to functionalize various linear polysaccharides to access polysaccharide-based advanced materials through chemical modifications (Furuhata et al 1995;Li et al 2009;Roy et al 2009). Silica gels coated with polysaccharide derivatives are, for example, now widely used as stationary phase for chiral separation (Ikai et al 2008;Sugiura et al 2010). The 3D structures of these polysaccharide derivatives are, however, distorted through conventional random modifications, mainly because of breakage of the essential hydrogen bondings (3-OH of cellulose, 2-OH of curdlan, etc.).…”