Separation of Alkyne Enantiomers by Chiral Column HPLC Analysis of Their Cobalt-Complexes
Qiaoyun Liu,
Jing Wang,
Junfei Li,
Xiaolei Wang,
Shichao Lu,
Xuan Li,
Yaling Gong,
Shu Xu
Affiliations
Qiaoyun Liu
School of Chemistry and Material Science, Shanxi Normal University, 1 Gongyuan Street, Linfen, Shanxi 041004, China
Jing Wang
School of Chemistry and Material Science, Shanxi Normal University, 1 Gongyuan Street, Linfen, Shanxi 041004, China
Junfei Li
School of Chemistry and Material Science, Shanxi Normal University, 1 Gongyuan Street, Linfen, Shanxi 041004, China
Xiaolei Wang
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A NanWei Road, Xicheng Distrct, Beijing 100050, China
Shichao Lu
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A NanWei Road, Xicheng Distrct, Beijing 100050, China
Xuan Li
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A NanWei Road, Xicheng Distrct, Beijing 100050, China
Yaling Gong
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A NanWei Road, Xicheng Distrct, Beijing 100050, China
Shu Xu
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A NanWei Road, Xicheng Distrct, Beijing 100050, China
Separation of the enantiomers of new chiral alkynes in strategic syntheses and bioorthogonal studies is always problematic. The chiral column high-performance liquid chromatography (HPLC) method in general could not be directly used to resolve such substrates, since the differentiation of the alkyne segment with the other alkane/alkene segment is not significant in the stationary phase, and the alkyne group is not a good UV chromophore. Usually, a pre-column derivatization reaction with a tedious workup procedure is needed. Making use of easily-prepared stable alkyne-cobalt-complexes, we developed a simple and general method by analyzing the in situ generated cobalt-complex of chiral alkynes using chiral column HPLC. This new method is especially suitable for the alkynes without chromophores and other derivable groups.
