al-Kindy S, Santa T, Fukushima T, Homma H, Imai K
Department of Chemistry, College of Science, Sultan Qaboos University, Sultanate of Oman.
Biomed Chromatogr. 1998 Sep-Oct;12(5):276-80. doi: 10.1002/(SICI)1099-0801(199809/10)12:5<276::AID-BMC747>3.0.CO;2-Y.
4-(2-carboxypyrrolidin-1-yl)-7-nitro-2,1,3-benzoxadiazole (NBD-Pro), 4-(2-carboxypyrrolidin-1-yl)-7-(N,N-dimethylamino-sulphonyl)-2,1,3 - benzoxadiazole DBD-Pro), 4-(N-1-carboxyethyl-N-methyl)amino-7-nitro-2,1,3-benzoxadiazole NBD-N-Me-Ala), 4-(N-1-carboxyethyl-N-methyl) amino-7-(N,N-dimethylamino-2,1,3-benzoxadiazole. (DBD-N-Me-Ala) have been synthesized for the resolution of enantiomers of amines by high performance liquid chromatography (HPLC). The reagents react with amino group at room temperature in the presence of activation agents, 2,2'-dipyridyl disulphide (DPDS) and triphenylphosphine (TPP) to produce the corresponding diastereomers. The derivatives were detected at lambda ex = 469, lambda em = 569 for DBD-moeity and lambda ex = 469, lambda em = 535 for NBD moeity. The resulting diastereomers were efficiently resolved using reversed-phase column with aqueous acetonitrile and aqueous methanol as the mobile phase. The elution order of the derivatives were D and L when proline was used as the chiral selector but the order was reversed when the diastereomers were prepared with the reagent containing N-methyl alanine as the chiral selector. DBD-Pro and NBD-Pro seem to give better separation as compared to DBD-N-Me-Ala and NBD-N-Me-Ala.
4-(2-羧基吡咯烷-1-基)-7-硝基-2,1,3-苯并恶二唑（NBD-Pro）、4-(2-羧基吡咯烷-1-基)-7-(N,N-二甲基氨基磺酰基)-2,1,3-苯并恶二唑（DBD-Pro）、4-(N-1-羧基乙基-N-甲基)氨基-7-硝基-2,1,3-苯并恶二唑（NBD-N-Me-Ala）、4-(N-1-羧基乙基-N-甲基)氨基-7-(N,N-二甲基氨基)-2,1,3-苯并恶二唑（DBD-N-Me-Ala）已被合成用于通过高效液相色谱法（HPLC）拆分胺类对映体。这些试剂在活化剂2,2'-二吡啶二硫化物（DPDS）和三苯基膦（TPP）存在下于室温与氨基反应生成相应的非对映异构体。对于DBD部分，衍生物在激发波长λex = 469、发射波长λem = 569处检测；对于NBD部分，在激发波长λex = 469、发射波长λem = 535处检测。使用以乙腈水溶液和甲醇水溶液为流动相的反相柱可有效拆分生成的非对映异构体。当使用脯氨酸作为手性选择剂时，衍生物的洗脱顺序为D型和L型，但当用含N-甲基丙氨酸的试剂作为手性选择剂制备非对映异构体时，顺序相反。与DBD-N-Me-Ala和NBD-N-Me-Ala相比，DBD-Pro和NBD-Pro似乎具有更好的分离效果。
