4-(N,N-dimethylaminosulfonyl)-7-(2-chloroformylpyrrolidin-1-yl)-2,1,3-benzoxadiazole: novel fluorescent chiral derivatization reagents for the resolution of alcohol enantiomers by high-performance liquid chromatography
4-(N,N-dimethylaminosulfonyl)-7-(2-chloroformylpyrrolidin-1-yl)-2,1,3-benzoxadiazole: novel fluorescent chiral derivatization reagents for the resolution of alcohol enantiomers by high-performance liquid chromatography
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4-(N,N-二甲基氨基磺酰基)-7-(2-氯甲酰吡咯烷-1-基)-2,1,3-苯并恶二唑：新型荧光手性衍生试剂，用于高效液相色谱法拆分醇对映体
DOI：
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发表时间：
1993
期刊：
影响因子：
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通讯作者：
K. Imai
中科院分区：
文献类型：
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作者：
T. Toyo′oka;M. Ishibashi;T. Terao;K. Imai
合成了光学活性衍生试剂4-（N，N-二甲氨基磺酰基）-7-（2-氯甲酰基吡咯烷-1-基）-2，1，3-苯并恶二唑[（R）-（+）-DBD-Pro-COCI和（S）-（-）-DBD-Pro-COCI]，用于高效液相色谱法分离醇对映体。这些试剂在吡啶存在下与羟基反应，吡啶作为催化剂与氯化氢反应。衍生自醇和试剂的非对映体的最大激发和发射波长分别约为450和560 nm。随着介质中乙腈浓度的增加，衍生物的发射波长略微向蓝色偏移;然而，激发波长保持恒定。用正相色谱法，以正己烷-乙酸乙酯为洗脱剂，有效地分离了脂肪醇衍生的非对映体。采用反相柱，以水-乙腈为洗脱剂，实现了不完全分离。当（R）-（+）-DBD-Pro-COCI用作衍生化试剂时，对应于R-构型的醇比对应于S-构型的醇洗脱得更快。正如预期的那样，当用（S）-（-）-DBD-Pro-COCI制备非对映体时，醇的洗脱顺序相反。疏水性醇衍生的非对映异构体的Rs值大于亲水性醇衍生的非对映异构体的Rs值。
Optically active derivatization reagents, 4-(N,N-dimethylaminosulfonyl)-7-(2-chloroformylpyrrolidin-1-yl)-2,1,3-benzoxadiazole [(R)-(+)-DBD-Pro-COCI and (S)-(–)-DBD-Pro-COCI], were synthesized to permit the separation of alcohol enantiomers by high-performance liquid chromatography. The reagents react with hydroxyl groups in the presence of pyridine, which functions as a catalyst and reacts with hydrogen chloride. The maximum excitation and emission wavelengths of the diastereomers derived from the alcohols and the reagents were approximately 450 and 560 nm, respectively. The emission wavelengths of the derivatives shifted slightly towards the blue with increasing acetonitrile concentration in the medium; however, the excitation wavelengths remained constant. The diastereomers derived from some aliphatic alcohols were efficiently resolved by normal-phase chromatography with hexane-ethyl acetate as the eluent. Incomplete separation was realized with a reversed-phase column with water-acetonitrile as the eluent. When (R)-(+)-DBD-Pro-COCI was used as the derivatization reagent, alcohols corresponding to the R-configuration were eluted faster than those corresponding to the S-configuration. As expected, the elution order of the alcohols was reversed when the diastereomers were prepared with (S)-(-)-DBD-Pro-COCI. The Rs values of diastereomers derived from hydrophobic alcohols are larger than those from hydrophilic alcohols.
使用改良环糊精缓冲液通过毛细管电泳进行碱性药物的手性分离和血清中布比卡因对映体的定量。
DOI：
10.1016/0021-9673(92)87133-s
发表时间：
1992
期刊：
Journal of chromatography
影响因子：
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作者：
Soini,H;Riekkola,ML;Novotny,MV
通讯作者：
Novotny,MV