アセチルカルニチン関連化合物の光学識別法の開発及び品質管理への応用に関する研究(博士論文要録)

概要

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Acetyl-L-carnitine (L-AC) has an effect of cerebral metabolism improvement. However, the enantiomer, acetyl-D-carnitine (D-AC), does not show this effect. Several methods for the determination of D-AC in L-AC have been developed, but they were not sufficient for quality control. The author has developed an indirect HPLC enantioseparation method and a direct one for the determination of D-AC in L-AC and NMR enantioseparation methods with chiral shift reagents. 1) AC and C could be separated with an ODS column by reversed-phase HPLC after derivatization with L-alanine-β-naphthy-lamide. 2) AC could be separated directly by reversed-phase chiral HPLC using SUMICHIRAL OA-6100 with a mobile phase of 2mmol/L aqueous CuSO_4 solution containing 500mmol/L NaClO_4. 3) The NMR method with (+)-(R)-18-crown-6 tetracarboxylic acid as a chiral shift reagent was successfully applied for determining of the enantiomeric purity of L-alanine-β-naphthylamide. 4) Enantiomer signal separation of AC was obtained on the NMR analysis by diastereomeric interaction with Pr[hfc]_3 as a chiral lanthanide shift reagent. These four methods were found to be applicable as practical quality control methods for the enantiomeric excess determination.
2007-02-05