Synthesis and chiral recognition of novel amylose derivatives containing regioselectively benzoate and phenylcarbamate groups.
A new class of regioselectively substituted amylose derivatives bearing three different substituents at 2-, 3- and 6-positions, and two different substituents at 2-position and 3-, 6-positions were synthesized by a sequential process based on the esterification of 2-position of a glucose unit. Their chiral recognition abilities were evaluated as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC). Each derivative had its own characteristic recognition ability depending on the arrangement of side chains at the three positions. Among the derivatives, amylose 2-(4-t-butylbenzoate) and amylose 2-(4-chlorobenzoate) series exhibited high chiral recognition. Some racemates can be efficiently separated on these derivatives as well as on the amylose tris-3,5-dimethylphenylcarbamate, which is commercially available as Chiralpak AD and one of the most powerful CSPs. The structures of the amylose derivatives were also investigated by circular dichroism spectroscopy.
Shen
Jun
J
School of Material Science and Chemical Engineering, Harbin Engineering University, Harbin, China.
Ikai
Tomoyuki
T
Okamoto
Yoshio
Y
D000688:Amylose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D001565:Benzoates / Q000138:chemical synthesis / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D002942:Circular Dichroism; D008958:Models, Molecular; D048448:Phenylcarbamates / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D001565:Benzoates; D048448:Phenylcarbamates; D000688:Amylose