Controlled synthesis and chiral recognition of immobilized cellulose and amylose tris(cyclohexylcarbamate)s/3-(triethoxysilyl)propylcarbamates as chiral packing materials for high-performance liquid chromatography.
The cyclohexylcarbamates of cellulose and amylose bearing a controlled amount of 3-(triethoxysilyl)propyl residue were synthesized by a one-pot process and efficiently immobilized onto silica gel through the intermolecular polycondensation of triethoxysilyl group. Their chiral recognition abilities were evaluated as chiral packing materials (CPMs) for high-performance liquid chromatography (HPLC). The immobilized CPMs exhibited comparable or higher recognition abilities than the conventional coated-type CPMs. The universal solvent compatibility of the immobilized CPMs clearly contributes to the improvement of chiral recognition for most racemates used in the present study. Interestingly, a significantly improved resolution for racemic trans-stilbene oxide (α=2.23) could be attained on the immobilized CPM using the eluent containing 30 vol.% chloroform in hexane, which cannot be used for the conventional coated-type CPMs. On the CPMs, almost no resolution of trans-stilbene oxide was attained by a typical eluent, hexane-2-propanol mixture (90/10, v/v). The novel immobilized CPM can also be used in thin-layer chromatography (TLC) due to the absence of an aromatic group.
Polymer Materials Research Center, College of Material Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China.
Jun
J
Shen
Shuangyan
S
Liu
Pengfei
P
Li
Xiande
X
Shen
Yoshio
Y
Okamoto
D000688:Amylose / Q000031:analogs & derivatives* / Q000737:chemistry; D002219:Carbamates / Q000138:chemical synthesis / Q000737:chemistry*; D002482:Cellulose / Q000031:analogs & derivatives* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation*; D002855:Chromatography, Thin Layer / Q000295:instrumentation; D008956:Models, Chemical; D009930:Organic Chemicals / Q000737:chemistry / Q000302:isolation & purification; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D002219:Carbamates; D009930:Organic Chemicals; D012821:Silanes; D002482:Cellulose; D000688:Amylose